19 Things A Well-Dressed Man Wouldn't Be Caught Dead Wearing… And What To Wear Instead


19 fashion mistakes to avoid making if you want to come off as professional, elegant, and dapper (even if you actually aren’t).

We all know that one guy that just always looks so cool and refined and polished, like they generally have their life together, right? Chances are, that’s the exact image he is actively trying to portray, and it is most likely coming from his careful choices in menswear and fashion.

When you want to sell a certain vision of yourself or portray a certain image, your clothing is your biggest advertisement platform. Not exactly sure what your current fashion choices are actually advertising? Then here are 19 mistakes to avoid making if you want to come off as professional, elegant, and dapper (even if you actually aren’t).

1. Don’t wear… sandals.

Unless you’re at the beach or in a public shower, skip the sandals. Flip-flops are easy and comfortable, but they are the worst shoe choice when it comes to portraying the image of a put-together man. If you want to be considered stylish, nix the sandals. Flip-flops? Never in public. And whatever you do, do not combine any sandal with socks!

Instead… try some alpargatas or other classic slip-on loafers (not penny loafers!). These shoes are nice and breezy and season-appropriate that still look stylish. For office wear in the hotter months, try perforated or linen leather shoes that will allow your feet to breathe.

2. Don’t wear…cargo shorts.

Not only do they scream «douchebag,» but they look sloppy and too casual. «But they have all these pockets for all my stuff!» you might say. Yes, but having your pockets stuffed with stuff leaves you looking lumpy, messy, asymmetrical, and poorly put together. Functionality is nice, but you are not a camel.

Instead… if you must go with shorts, get ones that provide clean lines, or at the very at least, asymmetrical and modest pockets.

3. Don’t wear.. a matching tie and pocket square.

Yes, even if your suit came with a matching tie and pocket square, that doesn’t mean you should keep them. If your tie matches your pocket square, you run the risk of looking cheap and gimmicky rather than expensive and polished. You don’t want to look so matchy-matchy that you’re mistaken for a game show host, do you?

Instead… find a tie and pocket square in non-clashing prints that share complementary colors.

4. Don’t wear… short socks.

Even if you think your shapely calves are show-stopping, keep them hidden. There is nothing more inappropriate than exposing those hairy man legs when you sit down because your socks are too short. Even if you shave your legs, it’s still inappropriate. It doesn’t matter how coordinated they are or how seasonally-festive they may be, socks are meant to be an undergarment, not the star of the show.

Instead… over-the-calf socks are a must when it comes to wearing dress pants. No excuses.

5. Don’t wear… a necktie with the button undone.

Choose one: keep the tie or undo the button. You cannot have both. A tie that’s tied over opened buttons makes you look sloppy and unprofessional, like that embarrassingly drunk uncle at your wedding. Also, this goes without saying: do not wear your necktie around your forehead unless you want to look like a frat boy who can’t handle his liquor.

Instead… If you’re wearing a tie and it becomes too hot, take off the tie, roll it up neatly, and put it in your pocket. Then, you can undo that top button to get some air.

6. Don’t wear… shirt collars that are too big.

When the collar is too big underneath a tie, there is a tell-tale puckering in the back because there is simply too much fabric. This bunching is unsightly and advertises that you don’t really know what you’re doing when it comes to fashion.

Instead… do yourself a favor: get properly fitted and purchase shirts in the right size. Two fingers should comfortably fit under your color, and there should be no visible gaps between the collar and your neck when you are standing still.

7. Don’t wear… square-toed shoes.

While square-toed shoes might be more affordable and easier to find, they are just plain ugly, generic, and tell everyone that you don’t know the first thing about style.

Instead… find round-toe or chiseled-toe shoes. They look much more polished and elegant.

8. Don’t wear… tennis socks.

Unless you’re at the gym or playing tennis, the occasions on which you would wear tennis shoes and socks are few and far between. Tennis shoes should only be worn out of necessity — never in the name of fashion, and wearing them with tennis socks just makes you look like a lost Disneyworld tourist.

Instead… wear ankle or no-show/invisible socks that will also help extend your leg line.

9. Don’t wear… a Windsor tie knot.

The problem with this ubiquitous, easy-to-tie knot is that it’s mostly worn with cheap, shiny ties. This makes you resemble more of a sleazy car or insurance salesman, rather than a dapper professional.

Instead… check out our video tutorial for the half-Windsor knot.

10. Don’t wear…. satin silk ties (during daytime).

In the evening, you may want to add some shine to your suit, but shiny, satiny ties should never be worn during the daytime. It looks as though you’ve stepped out of a Men’s Warehouse commercial.

Instead… wear a tie that’s silk and wool, or maybe cashmere, and has a matte look. If you are a fan of big prints on your ties but don’t want to look cheap and tacky, it’s particularly important to make sure it’s a matte look.

11. Don’t wear… sports sunglasses.

Unless you’ve got a frisbee in hand or are commanding a speedboat, these mirrored sports sunglasses have no home amongst your formal or professional wear.

Instead… go for classic sunglasses such as Aviators or Wayfarers.

12. Don’t wear…sports jerseys.

If you’re in a stadium cheering on your favorite game, great. If not, then leave the jersey at home. Your hometown pride will be overshadowed by the inappropriate and immature fashion choice.

Instead… support your team in a more refined way with a nice polo or collared shirt with a modest team logo.

13. Don’t wear… slogan T-shirts.

These t-shirts may be funny, but they are wildly inappropriate and tacky. You’ll come off as an angsty teen with something to say or a thinks-he-funny fratboy douchebag, rather than a polished and confident professional.

Instead… wear solids or refined prints that highlight your personality, not your T-shirt’s.

14. Don’t wear… a regular necktie to a black-tie event.

Just don’t. The requirements of the dress code are IN THE NAME of the dress code. If you wear something other than a nice, black tie, you’ll not just look out of place, but you’ll also be deemed illiterate.

Instead… watch our Black Bow Tie Guide to make sure you look as snazzy as the event you’re attending.

15. Don’t wear… a belt with a vest.

Even a modest belt buckle will be featured in the lower natural gap of the vest and will become a directional arrow to your crotch. Unseemly. Similarly, a necktie or shirt should never peek out from below your vest — it shows you don’t know what you’re doing because you can’t find a properly-fitting necktie or proper length vest.

Instead… Vests should only be worn with suspenders or just side adjusters. Make sure your necktie is the proper length and that the vest is long enough for your torso.

16. Don’t wear… a backpack.

Headed to the gym and hiking an expedition are the only times when a backpack is an appropriate choice for a grown man to cares about style. Otherwise, a backpack simply makes you look like an immature schoolboy off to hit the books, and the backpack’s bulk and weight can be dangerous and uncomfortable.

Instead… grab a nice leather satchel or messenger bag that can hold your gear but keep you looking your age and as a professional.

17. Don’t wear… too-long neckties.

A necktie that is too long for you does nothing but draw the eye to look at… your balls. So unless that’s the look you want to go for, make sure you purchase a tie in the right length according to your height.

Instead… shop our selection of ties for your perfect fit. Gentlemen’s Gazette is the only online retailer that offers all our ties in three different sizes — short, regular, and long — so that you are the focal point, not your grandchildren.

18. Don’t wear… suit jackets with large armholes.

Too big armholes on a suit jacket give you the look of a football linebacker or like a kid playing dress-up in his dad’s borrowed suit. They also restrict your movement and make you look sloppy.

Instead… get a properly fitting suit. Ask a professional to measure you. It’s easy.

19. Don’t wear… a big, gaudy wristwatch.

You might want to show off your 30-year Rolex or newest big bling, but let’s face it — a big, gaudy wristwatch is a scream for attention. It’s a show-off maneuver that doesn’t pay off in the right way.

Instead… aim for something understated and slimmer. Smaller watches look more sophisticated and ooze a sense of refined luxury much more than a snazzy, tacky wrist piece.

Key takeaways

If you’re trying to sell yourself as a well-polished professional man who’s got his crap together, making solid, fashionable choices about your wardrobe are key and these 19 tips are just the start. Whether you want to look powerful, elegant, fresh, or clean and polished, abide by these 19 rules to help you dress the part.