Men’s Style of Dresses For Office

Men are usually replenishment shoppers. You don’t often find them seeking new styles—they just want more of what they already have. They see a hole, a stain, or a worn collar and, bam, off they run to the store or the Internet to replace their favorite items. Ladies, we could take a cue from this style of shopping.

The biggest challenge for men? Taking a minute to look in the mirror and see whether what they have on actually fits. I was recently in a client’s closet, and on the floor were boxes and bags full of newly purchased Jos. A. Banks shirts, pants, and suits. And when I say “newly purchased,” I mean purchased within the last six months. My client had stopped by his favorite store on a sale day to take advantage of the low prices and shopped to his heart’s delight. 

However, it turns out my bargain-seeking shopper had not looked in the mirror in a very long time, because nothing he bought (or owned) really fit. And, by buying so much stuff on sale that didn’t fit, he had actually spent more money than his wife, whose case he sometimes got on for buying full-price items (though her items always fit, and she did buy less than he).

When it comes to fashion, most women think the men in their lives have it pretty easy. And yet, while men have fewer pieces to coordinate and easier maintenance directions on their labels, some still manage to walk into work looking like slobs. The most common complaint I hear is about men in wrinkled or stained clothing. 

If the obvious pen mark you got on your shirt last month has remained intact after a visit to the dry cleaner, it’s time to let it (or your cleaner) go. If you often stain your ties with food, keep a few spares in your desk drawer. One of the quickest ways to lose respect in the boardroom is to look messy or neglectful of your hygiene and appearance. There is an expectation that a smart presenter also be a neat dresser.

Men’s style is mostly about fit. Of course, there are a few rules: match your socks to your pants instead of to your shoes. Update your belt if you move notches or the leather begins to come apart. (If you are losing weight reward yourself, and if you’ve just gained a few pounds, camouflage it.) Polish your shoes. Make sure your clothes are wrinkle-free. Never wear more than two rings, and consider your watch an investment piece.

A polished and successful image is based on the proper fit of your clothes. Are you drowning in an oversized dress shirt, or does your slim-fit shirt pull desperately at the buttons? Are your trousers baggy, tapered, pleated, or all three? Did you polish your shoes last week or last year? These are just a few of the parameters within your control and on which colleagues will judge you. Men (and women) may not always recognize the brand another man is wearing, but it is relatively easy to tell if a coworker maintains good hygiene and takes pride in his professional appearance.

Traditionally, men have measurements they follow and styles they inherited from their fathers, brothers, bosses, or style mentors. My aim is to tell you what’s in and out for you and help you understand the importance of looking in the mirror and identifying a proper fit so that you stay relevant and stylish as you climb the ladder of success. I’d hate for you to be sideswiped by the guy wearing the right tie just because you weren’t paying attention in Fashion 101.

Let’s review some of the style basics about clothing that’s already hanging in your closet or can easily be purchased to update your wardrobe and help you dress to impress:

  • Shirts
  • Pants
  • Suiting
  • Sweaters and outerwear

Shirts

Does quality make a difference? Sure. But also keep your lifestyle in mind. My husband and I lead a busy life, and he loves his iron-free shirts. For these, we go to Brooks Brothers slim-fit custom shop. Online or in store, you can design to your heart’s delight dress shirts that will stay wrinkle-free and can be easily maintained. Priced very closely to off-the-rack shirts, they are a great alternative. 

If you prefer to avoid the outrageous prices at your local dry cleaner, then iron-free material that can be maintained at home is more important than high-luxury linen. While the material should feel nice, your highest priorities should be fit, budget, and a commitment to maintaining and wearing your clothes. Just as women often do—with First Lady Michelle Obama leading the pack—men should feel free to mix high and low pieces for effortless and unique style.

When buying off the rack, check the quality of the buttons; a cross-stitch anchoring a thicker button is a good indicator of its durability. Make it a priority to get measured to ensure the perfect fit.

And, no, you cannot measure yourself. I recommend heading to a quality men’s shopping destination to find out your size. (If you live near a Nordstrom, that’s always a good bet.)

Style

Every ensemble involves wearing a shirt. Learn how to diversify your collection and personalize your look.

Color

I have never been in a guy’s closet that doesn’t have white and blue shirts. Some have only white and blue shirts…and I beg them to include more colors! Others are color hounds and wear a white or blue shirt only if a conservative situation arises. I am a big fan of blue—just vary the shades. Play around with baby blues, French (saturated or medium) blue, and every shade in between, and experiment with textures and weaves. This is the baby step before we move into patterns.

Next up is white—if you love the look of a crisp, white shirt, run to your closest white shirt bar. Thomas Pink offers more than thirty styles of white shirts, making it easy to have fun with this simple classic. Add a texture like herringbone or tonal stripes for a little more style.

Adding color to your work staples will freshen your look and help you stay current. I like pinks, lavenders, stripes, and squares. Stick with lighter shades of pink and purple, and when wearing stripes keep in mind whether you will be matching them to a tie. Fine stripes are easy to wear for the everyday Joe; Bengal (medium) and butcher (medium-wide) stripes are flashier choices for the aficionado. Windowpane and square patterns are a personal favorite because they flatter most body types and come in a variety of sizes and colors. Pinpoint, twill, herringbone, hairline stripes, broken stripes, gingham, and grid styles will also help you round out your wardrobe choices.

Cuff

French or barrel? Monogrammed or left plain? Cuffs are another way to show off your unique personal style. There is a certain elegance to a cuff, and you want to be sure you choose the style that is comfortable and works for you. A button or barrel cuff is classic and perfectly appropriate in most work situations. French cuffs, which require cufflinks to secure around the wrist, are typically more formal, yet offer an opportunity to display a bit of flash for the fashion-forward gentleman. If your wrists are too skinny, cufflinks can make it appear as if you’re wearing your father’s shirt. If your cuff links are too big, they will look ostentatious instead of accenting your overall look.

Many of my clients wonder whether cufflinks will make them appear too slick. Historically, shirts with cufflinks were perceived as something worn only by the wealthy or for special occasions. While that stereotype has certainly changed, there is still a common misconception that wearing cufflinks—or even a nice watch—makes you appear “rich.”

I meet with a lot of government contractors, politicos, and professionals who delicately walk the line between the private and public sector. My best counsel regarding this accessory (and many others) is that if you remain true to yourself, you won’t look overdressed at work. Learn to dress for your audience while being mindful of your own personal and unique style. Being authentic is often admired in fashion—hence signature style statements like Hermès ties, pocket squares, tie clips, cufflinks, or even loud socks.

Mitt Romney is a great example of someone who has struggled to appear relaxed in casual clothes for years, and whose jeans and unbuttoned collars often came across as awkward to voters during the race for the White House in 2012. A costume always looks phony, and Romney was clearly more comfortable in the tailored suits and crisp ties from his private-sector days than the “working sleeves” uniform of a campaign. Authenticity trumps phoniness every time.

Button-Downs, Short-Sleeve Shirts, and Polos

When should you wear a button-down collar? First, let’s define what “button-down” means—it refers to collar type. This is the most casual of dress shirts and the most formal of casual shirts. It’s a choice we often see college students or the younger set make, and it’s also popular for any age in academic, science, and nonprofit workplaces. 

This kind of shirt is not meant to be paired with a tie, due to its more casual nature; however, in any of the aforementioned industry categories, you are likely to see it with a tie and sport coat. Anytime I see a guy on the news in a button-down with a bow tie or maybe a knit tie, his uniform screams reporter, “expert,” or author. Not a bad thing, but it does brand you.

The short-sleeve shirt is often paired with cotton pants in the summer and is definitely only a casual option for the office. Similarly, a polo shirt should be worn to work only on a day deemed to be that casual. Stay away from logos at the office—I have yet to write a dress code where an employer allows them at work (unless it is a company logo). 

Fan of the 49ers? Wear it on the weekend. And that applies even to the “nicer” one you bought for the Super Bowl luxury box you sat in with your boss (on a weekend). Striped polos are more casual than plain ones. Ideally, look for one with cuffs in the same material as the shirt—therefore, not the same polo you would wear on Saturday with the kids eating pizza.

Golf shirts are a favorite at work for many men I know. But even if you are hitting the links that day, please don’t wear your golf shirt to work unless it is logo-free and blends in well enough to look like a regular shirt. Performance tops are not usually included in dress codes—not even high-end ones from your vacation at the Ritz-Carlton. Yes, there are exceptions to every rule, but try to follow this one the best you can.

Generally, the button-down, short-sleeve shirt, and polo are great for a business-casual environment, casual business travel, resort casual, or a weekend networking coffee date.

Fit

Men’s shirt selections have evolved to include a variety of fits for different body shapes. Don’t be intimidated by labels; try on new fits and select the one that works best.

Classic

There was a time not that long ago when most men and women thought there was only one shape of shirt for every man. The classic cut is what most men have worn throughout their professional careers. This style is cut full through the chest, waist, and armholes and has traditionally been sold at most men’s retailers. Most suitable for the stocky and broad guy, it has also been worn by lean, trim, and tall guys. Now there are many newer styles to choose from, so make sure to check your options before just replenishing this traditional, oversized fit.

Style Alert: The modern professional looks for dress shirts without a great deal of excess material in the body.

Slim

The newest style to hit shelves and closets across America is the slim fit. Initially, this style was perceived to be for the thin or fashion-forward guy. However, with so many cuts to choose from even the athletic guy can now sport a slim-fit shirt. Each retailer or designer has its own version—from the extra-slim-fit to the trim-fit. The term does not mean the same thing at every store and some cuts are more generous than others. Proportions should flatter your physique whether you weigh one hundred and fifty or two hundred and seventy-five pounds.

Extra Slim

Don’t be scared of the “extra” part! I have put men over fifty years old in extra-slim-fit shirts. It doesn’t necessarily mean you look ready to hit the clubs. This style is truly suitable for both the slim guy and one who is compact and shorter. Depending on the designer of the shirt, it can work really well for the wearer who is still swimming in a trim cut or whose shoulders don’t quite measure up in a slim cut. If this sounds like you, go on and try it.

Style Alert: Even if you don’t have a trim midsection, you may still be able to wear a slim-fit shirt.

Undershirts

Whichever style of shirt you choose, make sure to assess your undershirt needs. An undershirt can be effective for absorbing sweat, covering chest hair, shoring up see-through shirts, and even offering control. 

I have clients who won’t leave home without their Manx on for compression. Just like Spanx for women, Manx help you stand taller and suck it in. You don’t have to wear undershirts to work, but if you have chest hair that protrudes from your collar or are constantly sweating, I highly recommend them. Calvin Klein makes a style with Modal and Lycra that I particularly like because it is lightweight and does not add bulk, and Banana Republic has one in pima cotton with stretch that also works well. Remember, if we can see the collar of your undershirt, make sure it is not yellowed or worn. Don’t overlook this category!

Collar

A collared dress shirt should be found in almost every working man’s wardrobe. And there are so many collars to choose from—a spread collar, an extreme-spread collar, a curved collar, and a button-down collar. Maybe you prefer a more academic look in a button-down collar or a more conservative point collar (very popular in the hallowed halls of D.C.). 

Perhaps you march down Wall Street wearing a banker’s collar (white, to contrast with the shirt color) or dance to the beat of a club collar (with thinner, rounded edges). Chances are, the everyday working Joe is choosing either the popular point collar, which works well with a four-in-hand knot style, or the trendier medium-spread collar, which is wider and allows for a Windsor or half-Windsor knot.

I love how Thomas Pink, Banana Republic, Brooks Brothers, and even Men’s Wearhouse design exclusive collections. Affordable style exists at every price point. And you don’t need to fly to Hong Kong for a custom design. When you are out there shopping, I want to help you match your body type and face shape to the right collar style.

Spread Collars

If you have a more angular jawline, any version of the spread collar will help you seem to stand taller and even bulk you up a little (making it appear as if you go to the gym even if you don’t). A wider collar broadens the torso and lends the shoulder a strong shape. I love the spread collar, because it holds the eye of your audience and keeps them engaged—great for interviews and standing presentations as well as everyday wear.

Style Alert: Spread collars are almost universally flattering!

Point Collars

The narrow-point collar has long been a standard style in a gentleman’s shirt wardrobe. Considered by many to be the only shirt style to be worn with a tie, it is favored by the more conservative wearer and is a longtime favorite of many men in politics. However, when you choose a point collar, you are directing your audience to look down rather than up to eye level. This is not always a flattering direction. There are different versions of this collar, some narrower than others, but the direction remains the same (toward your midsection and beyond). Still, this style is great for a man with a lean physique who is testifying in court or attending a serious meeting in a conservative or traditional environment.

To any lost (fashion) sheep: be careful when choosing a trendy collar. The club collar may be “in,” but it isn’t for everyone. Just as a banker’s collar matches the business/finance/possibly old-world job industry (picture cigars on the balcony after work), this collar style works well on the slim and young-spirited. If you don’t fit the body type or emotional description of the style, wear a different shirt.

Going Custom

People often wonder, “Should I spend more than I’m accustomed to for better quality?” My main question is always, “Does it fit right, and will you wear it?” The short answer to whether you should invest in custom shirts or even a custom suit is to first analyze your body type. If you are unable to shop off the rack—maybe your shoulders are too broad or your arms too long, then custom is the way to go.

There are also a few versions of custom—you can visit a tailor to design a shirt from scratch or just to alter the length in the arms, if that is your challenge. I have quite a few clients with unique arm measurements (thirty to thirty-two inches, which is on the short side) who love shopping off the rack and have found shirts that fit in the body but just need to be shortened in the arms. Easy! Do it! Have a tailor on speed dial, or if the retailer offers tailoring, take advantage.

If you have extremely long arms, do not settle for wearing shirts with sleeves that are too short—they will not look right. I am going to repeat this, gentlemen: shirts, where the cuff hits at or above the wrist bone, are too short. If this is your style challenge, take it as an indicator that you cannot buy shirts off the rack and must get them custom-made. If you are wondering if this is you, remember that your shirtsleeve should extend a half an inch beyond your jacket sleeve. Similarly, if your neck size is unusual, you are probably a good candidate for custom shirts.

For the true style guy, there is no option other than custom. Time for a new suit? Off he goes to the tailor. This is not for everyone, but if you enjoy having a hand in creating and designing your clothes, custom tailoring is great. And monogramming your shirt cuff or the lining of your jacket lets the world know you are a true auteur of style.

Matching Shirts to Suits and Ties

Matching it all together is the most challenging part of the dressing process. Too many men choose to wear plain shirts or ties because they are worried about their skill in putting together a full ensemble. Once you identify the right fit for you, scale and proportion are key. The scale of the pattern on your tie can be larger or smaller than that of your shirt, but it should not be the same.

Similarly, the scale of stripes or pattern on your suit or sport coat should be different from that of your shirt. For example, when you wear a large check-patterned shirt, the design or weave on your tie should be small or tight (like a dot or spot style). When you wear a finely striped shirt, choose a boldly striped tie. The juxtaposition of large and small makes both of these stylish and successful looks. See page 70 (Neckwear) for more tips.

When choosing a tie, select colors that echo those of the shirt. Prints (like paisley, dots, animals, or floral) set against stripes work well when the shades are similar but the scales differ. If you indulge in busy patterns with your shirt and tie, keep your suit or sport coat neutral. Consider polishing off your look with a pocket square. The easiest way to add this accessory to your look is to select a well-pressed white linen one, neatly folded so there is a sliver of material protruding from your outer chest suit pocket (no more than a half inch). If you want to be a little flashier, choose a patterned style or a pocket square with colored edges that coordinate with your shirt and tie.

Pants

An ill-fitting shirt can be hidden underneath a jacket, but pants that are too big, too tight, too long, or too short, will always be obvious. Make sure the pants hanging in your closet match your current shape.

The Pant Front

The first thing I look for when I sift through a new client’s closet are pleated pants. And you know what? I rarely find a senior executive’s closet without them. My best advice: if you own them, run home and throw them out. 

There is usually one of two reasons you own pleated pants: you belong to a generation that believes in wearing only pleated pants, to maximize the space in the seat area, or you are so fashion-forward (and chances are you are also young) that these pants speak to you and tickle your style fancy. A third reason could be that you haven’t cleaned out your closet in a long, long time.

Flat-front pants are universally flattering. They happen to be having an “in” moment now, but they will always be on my list of must-haves. Sometimes a trend comes along that is just so good it weaves itself into the history of fashion: the flat-front pant is one of those items. In fact, many men in their twenties don’t know any different, while some in their sixties are still trying to come to terms with this shift in style. 

Pleats were once regarded as more formal than flat-front pants, but now they just look conservative or outdated, depending on the wearer (unless that wearer is tall, lean, and the “style guy” at the office). As for the “extra room in the seat” that pleats were once so fondly regarded for providing, men and designers of men’s pants have adjusted their expectations and now happily meet in the middle.

Traditionally, a flat-front pant has a plain hem, while cuffs have accompanied a pleated front. The pleat-and-cuff combination draws a lot of attention to the bottom half of the wearer. The fuller cut adds the illusion of weight, and the cuffs make your legs look more compact. 

Cuffs are directly related to height, so if you are challenged in that department, keep in mind that cuffs will make you appear shorter. (On the opposite extreme, the extra-tall professional athlete often struggles here as well, because adding cuffs to shorten the legs will once again draw attention to them.) I simply don’t recommend this style for the everyday man.

Style Alert: If you are a size 36 waist or higher, pleated pants will make you appear bigger.

If your closet is full of pleated, cuffed pants, you have a couple of options. One is, clearly, to go shopping. The other is to have your current pants altered, to both remove the pleats and release the cuffs. (From a style perspective, single-pleated pants can go without cuffs; double pleats should have cuffs.) If you are an average Joe, five feet eight or shorter, with a size 36 waist or higher, start alterations and hit the stores.

Style Alert: Flat-front, plain-hem pants work on every height, weight, and physique.

The Break

One of the most commonly asked questions from clients is, “Where should I hem my pants to create a break?” This is the dimple or soft gathering of fabric above the shoe on the front of your pants. There are three answers, depending on the look you want. 

The style guy may go for no break and sport the shorter-style pant that hits the top of the shoe, showing off a printed sock. The “working at my desk until 2:00 a.m.” guy (you may know him as the one with stains on his tie and sleeves rolled up all the time) may go for a full break, with just a bit of bunching over the top of the shoe. 

The full break allows for material shrinkage but often just looks like excess fabric at the bottom of the leg. My preference is a mid-break, which ends about one inch above the top of your shoe’s sole. This is neat and smart looking, and sends a neutral style message based on a good fit. The break in your pants is not the place to flex your fashion muscles.

Khaki: A Color or a Material?

The term “khakis” generally refers to the cotton variety of pants, though you will often see it as a color descriptor. These have evolved from casual wear, to iron-free and work-appropriate. The brand Bonobos identified the gap in the market for stylish, casual pants at the office, and I often recommend their styles to clients. 

Khaki-colored pants work well paired with a casual dress shirt, brown belt, and brown shoes, in warmer weather. During the winter months, and to add variety to your business casual wardrobe, stock up on gray and black iron-free dress pants (or just commit to visiting the dry cleaner or using an iron) to pair with button-downs and sweaters, and black accessories.

All pants are not created equal. Cotton-based khakis are different from wool gabardine pants in a khaki color. And a wrinkle-free pant is different from a wrinkled one. In a business-dress environment, the best pant when you’re not wearing a suit is made of gabardine. Of course, keep climate in mind when deciding the material of your trousers. You will want a luxurious and crisp pant; in Miami, that may be a cotton blend, while in Boston it may be wool.

The first colors to include in your dressier trouser wardrobe will be navy and charcoal. They are great base colors that are easy to match and work well with sport coat, shirt, and tie combinations. As you build your professional wardrobe, add medium to light gray, tan, brown, and black trousers to the mix. Just remember, chocolate-brown accessories and black clothes don’t match!

Suiting

The suit is the uniform of the boardroom. A wardrobe staple worn for the past hundred years, it has certainly evolved. Despite such changes as lapel width and number of buttons or vents, as well as changes in industry dress codes, the suit remains the very definition of a power ensemble. Silicon Valley dressing may work in limited environments, but a great-looking suit will work everywhere. A suit keeps you looking important when others don’t, and it projects an aura of power. In fact, its tireless uniform appeal is attractive to many women who mourn the day women’s wear began offering so many choices!

In the last ten years the suit has evolved for many from an everyday staple to an “only when I meet with clients” ensemble. The one constant requirement is that, whether you’re wearing the suit to your first interview, to a client meeting, to ring the bell on Wall Street, or to celebrate closing a deal, it must fit you well. 

The best part about our fashion climate right now is that accessible, affordable fashion is more widely available than ever, so you don’t need to spend a fortune on the suit, as long as you spend a little on a good tailor. I’ve worked with tailors across the globe to customize suits, and I have fooled even the best of eyes with fabulous suits for $250 (I love Alfani at Macy’s.) I’m not saying buy your suits at cheap-chic locations, but good quality (especially if you take care of it) is attainable on a budget. Buying a suit is an investment.

Off the Rack or Custom?

Suits are meant to be altered. Walk into the shopping experience aware that chances are very low you will be able to wear the suit you find the following day. Most high-end and luxury labels still sell suiting in the traditional manner of a “nested suit.” Here, jacket and pants coordinate in size and come as a set. The hem on the pants will usually be unfinished and the jacket will need to be adjusted.

A newer style of off-the-rack suiting is suit separates. Here, you can choose items closer to your exact size. For example, you may find more precise matches to your sizing, like a 36 x 32 pant and a 44 regular jacket. (This size jacket would usually carry a 38 pant.) 

Suit separates are a great solution in a struggling economic climate—wonderful for new grads, job seekers, and daily suit wearers who crave variety. I often find that suit separates mirror the custom suit better than a nested suit, even though a nested suit, which typically costs more, may be made of a higher-quality fabric. And with separates, you can buy an extra pair of pants to maximize the longevity of your suit—a suggestion I often make to clients buying custom suits.

Style Alert: Reinforce the seat of your pants to avoid a split hem and, whenever possible, purchase a second pair of pants to lengthen the life of your suit.

If you are just starting your suit collection, begin with one navy and one gray suit in tropical-weight wool. Navy looks sharp on almost every guy and is easy to match for even the novice dresser. A plain navy suit can be versatile if you are looking to make the most of a limited wardrobe—the jacket turns into a blazer with jeans or trousers, and the pants can always be worn on their own with just a dress shirt. Your second suit should be a medium to charcoal gray—either plain or with a light pinstripe.

The trick to selecting the right kind of pinstripe is to stand about ten feet away from the mirror—if the suit looks mostly like a plain color with just a faint hint of a pinstripe, then you’ve nailed it! If you can really see the pinstripe, this now becomes a memorable suit—a challenge when you are working with a limited wardrobe and budget. Your overall polished image should be what your audience remembers; you don’t want to be thought of as the guy who always wears the pin-striped suit.

Once you have developed your suiting wardrobe, delve into brighter pinstripes, herringbone, or colors like khaki and light gray; shades of blue, brown, or olive; and seasonal fabrics like linen and seersucker.

Fit

Whether you select a custom suit or shop for a look-alike, keep in mind a few fit guidelines.

Jacket sizes are as follows, in correspondence with your height:

Short—Up to 5’9”

Regular—5’10” to 6’

Long—6’ to 6’4”

Extra Long—6’4” and up

Shoulder

The way a suit fits in the shoulder is key and will often tell you if you need to pursue a custom option. The jacket should not pull across the back, and the shoulder pads should end at your shoulders. Be sure to look in a three-way mirror and assess the situation with the tailor. If there are too many horizontal lines, your jacket is too tight; if there are too many vertical ones, it is too big.

Collar

Your jacket collar should sit flush against your dress shirt’s collar, revealing one half inch of your dress shirt (collar) in the back.

Cuff

A suit jacket is traditionally meant to fit shorter in the arms than other jackets. Your shirt should show about a quarter to a half inch below the jacket cuff. This means your jacket will end at or around your wristbone.

Length

A suit jacket should end after your backside does. Typically, it should hit at the bottom of your backside, or where your knuckles land when your hands are by your sides. If it doesn’t, make sure you are not mistakenly wearing a short or long.

Style Alert: Like all rules in fashion, these rules are not hard and fast. I have put someone who is “short,” at five feet eight inches, in a regular jacket instead of a short one because a style was more contemporary and better suited to his physique. And keep in mind that fits can change at different stores. Knowledge is power in creating your look!

Vents

Jackets either come with one center vent, two side vents, or no vent. Historically, the center vent is a more casual American style, side vents an elegant English feature, and no vents Italian. When there is an option, I tend to prefer side vents because they keep a clean line on the jacket as you readjust throughout the day (from sitting to standing, moving hands in and out of pockets). Stay away from a jacket without any vents unless you chose to customize this style for your physique.

Jacket Style

Men have the option of single- or double-breasted suits. While they’ve both had their moments in fashion history, I lean toward the single-breasted suit. A double-breasted suit can look dapper on the right individual, but it makes most men look bigger in the midsection (or just plain old and dated). 

If you are taller, you can go with three buttons on the torso; otherwise, a two-button suit on which the buttons are located a bit higher than they are on the suits from the ’70s is very flattering. With regard to fit, the top button on a two-button suit, or the middle button on a three-button suit, should not hit below the navel. These are also the same (and only) buttons you should close on suits.

Guidance for Going Custom

If you choose to have a suit custom-made, indulge in some of these touches to show off your investment, even if you’re the only one who will appreciate these personalized features.

Lapels

Choose from a peak, notch, or shawl lapel. A wider, more angular peak offers dramatic flair, while a softer, rounded shawl is most often seen on a tuxedo. The notch lapel, with a well-defined “notch” separation between the upper and lower lapel, is standard and always stylish.

Buttons

Working buttons on the sleeves, also known as “surgeons’ cuffs,” are evidence of a custom suit, and a lapel buttonhole is a final flair. Opt for stitching in contrasting colors on either or both of these areas to really show off your investment. If you’ve gone this route, flaunt it!

Ticket pocket

A ticket pocket goes above the right hip pocket and is a signature feature many men choose to include on custom suits. You may not ever put anything in there, but the fact that you can distinguishes you from the average Joe. I like all pockets at the waist to be straight rather than curved, to minimize hips.

Lining

When that jacket gets slung over a chair at your next meeting, make a statement. Choose a lining in a bold color or fun pattern that is uniquely yours. You can also choose to line the material under the collar and, of course, have special monogramming done on the interior pocket. When I was growing up, my mom and I would include hidden messages—“I love you” or “Best Dad”—in my father’s custom clothes.

Sweaters and Outerwear

In the winter, your heaviest layer may be the one your audience notices first. Whether it’s the sweater you wear all day at the office, or the coat you arrive wearing to a meeting, make a positive impression.

Sweaters

If you work in a business-casual environment, sweaters may be a part of your uniform in the winter. Opt for elegant styles in wool or cashmere blends. Quarter-zip and polo styles are among the most professional and flattering options. Crew-neck and V-neck sweaters, as well as cardigans, are traditional styles that are acceptable at the office. However, they draw attention to your midsection, so avoid them if you carry extra weight. Turtlenecks can also be appropriate at the office, but beware of mock necks as they can look dated and old.

Style Alert: Examine your sweaters every year and stop wearing to work those that are pilling, stretched out, or even slightly moth-eaten.

Coats

Dress for the climate you live in, and save the purchase of a coat for last if you don’t need it daily in cooler weather. If you will be wearing a coat to work, make sure it fits as well as your clothes (and has room underneath). I lean toward versatile styles with removable liners. Knee-length trench coats or sporty raincoats work well and match most business-casual (or dressier) attire. In the colder months, look for a winter coat that features clean lines and a simple style to avoid bulk.

Workplace Dressing Dos and Don’ts

Do avoid pants with pleats: they will give your slacks a dated look and add weight to your frame. Choose a more slimming, stylish flat-front design.

Don’t force yourself to choose between comfort and class. Oxfords and loafers can combine the formality of a dress shoe and the comfort of a sneaker. Wear them for work and play.

Do inspect your clothes for evidence of wear and tear—unpolished shoes, frayed cuffs, and underarm stains are not professional.

Don’t underestimate the importance of good grooming—make sure your routine includes a broad range of meticulous personal habits from regular haircuts to trimming fingernails.

Do match your socks to your pants —elongate your frame and streamline your look. Matching your shoes to your belt will break up the outfit appropriately. Avoid bulky belts with gaudy embellishment.

Do look fresh and invest in iron-free shirts or a steamer, or frequent the local dry cleaner to avoid a rumpled, tired look.

Don’t use your work wardrobe as an opportunity for misguided self-expression—steer clear of novelty ties, oversized jewelry, logos, and anything that attracts too much attention.

Do dress for the weather—light layers and natural, breathable fabrics will allow you to control your own temperature. Don’t wear flip-flops, boat shoes, or Crocs in the summer or bulky hiking boots with a suit.

Don’t overexpose yourself—tattoos and piercings should be covered at appropriate times. Don’t allow wardrobe malfunctions to hurt your chances for career advancement.

Parting Thoughts

Men are lucky! You don’t need to have flair to be well dressed. Choose to dress up instead of down, know your size, understand proportion, and make it a priority to look neat and polished. Maintaining a wrinkle-free, well-groomed appearance is a goal even the most style challenged fellow can attain.

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