Nearly a decade ago, we published one of our most divisive videos on the things men should never wear. It struck such a nerve that people filmed their own reaction videos to it. We decided it was time to revisit the subject, this time with two of us trading pet peeves and, on a couple of items, flatly refusing to agree.
New Video
We Revisited the List, and Argued About It
Two of us sat down to trade our biggest style grievances. We agree on most of it, from sneakers with a suit to novelty socks, but two items nearly started a fight: crew-neck sweaters and Belgian loafers. The full list, the reasoning behind every pick, and both debates are in the video.
The Original List That Started It All
I know some of you will say, in this day and age, I can wear whatever I want, and you’re quite right! Today, you can wear whatever you want at the same time, you can also inhale asbestos, or you can drink water from lead pipes. Just because you can, doesn’t mean you should.
19 Things That Should Not Be In Your Classic Wardrobe
1.Sandals
They look particularly bad when you combine them with socks but even on their own, they may be something that people who are really into outdoor stuff wear, however, if you consider yourself stylish or if you care at all about your outward appearance, sandals will always make you look less smart and immature.
The same goes for flip-flops. Unless you’re at the pool or at the beach; a self-respecting man should never wear flip-flops in public. It’s always easy to say what not to wear but what should you wear instead? Well, for summer, I think an ideal shoe is alpargatas, they’re actually shoes that are originally from Majorca. Sometimes they have some rubber added to it and then it’s fabric sometimes it’s woven, sometimes it’s very thin. In any case, it’s a summer shoe, it’s airy, it serves the same purpose of sandals or flip-flops. Yes, it’s a lot more stylish.
If you want to go a notch up in formality, go with perforated punch holed leather shoes, or maybe even linen because it absorbs the moisture from your feet and it looks very summery and elegant.
2. Cargo Shorts
They just make you look like a douche bag, and I know some people love them because they’re functional. Having items in a cargo shorts pockets make you look asymmetrical and because of that, it sends a subconscious signal to others that you’re just not as well put together and they can’t put their finger on it but in any case, they will think less highly of you.
3. Matching Tie & Pocket Square
Oftentimes, they come in sets; usually in ugly, shiny satin and sometimes they even pre-fold pocket squares or pre-tie ties that you clip on and if you wear this, it just looks so cheap and like you don’t know what you’re doing, that you’re better off skipping it altogether. Of course, wearing a tie and a pocket square makes you look dapper and you should do that, however, you should always tie your own tie and fold your own pocket squares. If you’re not sure on how to do that, we have a whole series on different tie knots and how to tie them, as well as how to fold pocket square the easy way, please check them out.
4. Short Socks
My fourth style pet peeve is wearing a suit with short socks. No one wants to see your hairy calves and even if you shave them, it’s just not appropriate especially in a business setting or an office setting, and if you go with a suit, or with long pants, or trousers, or dress pants, you should always have over the calf socks.
How To Combine Socks, Shoes & Pants
5. Unbuttoned Dress Shirt With A Necktie
It just looks sloppy and the sole purpose of wearing a tie is to make you look more dapper and elegant. There’s no functional, no practical reason why we wear a tie, having a top button undone just looks like you don’t care about how you look and you should either wear the tie and wear properly, or not at all. So you find yourself in a situation where it’s too hot, or you feel uncomfortable around your neck, take out the tie, roll it up, put it in a pocket and unbutton the buttons, that looks much better.
6. Big Shirt Collars
I see them all over the place and sometimes you wear them with neckwear which leads to puckering because when you tighten your tie knot, there’s too much fabric and it just leaves unsightly waves. The golden rule of thumb that you read all over the place is that you can put two fingers in your collar and it should comfortably fit. The problem with that is, I’ve never found a collar where I couldn’t put two fingers in because your neck is flexible, because of that, you should wear a collar that doesn’t leave any visible gaps when you stand still. Usually, if your collar is too big, you’ll find that there’s a gap in the front and it should sit snugly against your neck, that will give you a proper look and it’s just dapper.
7. Square-toed Shoes
Usually, it’s what you find in lower end shoes under $100 and they’re just plain ugly and they show everyone around you that you have no clue about dressing well. When I grew up in Germany, there was a company named Lloyd’s and they sold tons of ugly shoes and they were actually a little more expensive so people consider them to be quality dress shoes and for that reason, that style was perpetuated. Fortunately, there are lots of other good companies out there that offer a nice round toe or if you want something a little more square, go with a chisel toe that’s very elegant.
The 4 Biggest Men’s Dress Shoe Mistakes & How To Avoid Them
8. Tennis Socks
Unless you’re at the gym, there’s really no reason you should ever wear them. Wearing white tennis socks with brogues, or with long pants, or even with shorts, in a public setting that is not the gym, make you look like a peasant.
9. Windsor Tie Knot
I know it’s one of the most popular tie knots around because it’s symmetrical and it’s big. The problem is, most people wear it with cheap shiny ties and it makes you look like a used car salesman or an insurance salesman, that is just very sleazy and not pretty competent instead, I suggest you look into the many different tie knots that are out there including the half-Windsor that look much better in my opinion, and are much better suited to an elegant gentleman.
10. Satin Silk Ties
Especially not for day wear! If you want something for the evening, or you want a little bit of shine, I could see that; but most of those ties you get at Walmart or a cheaper outlet like Men’s Wearhouse, and you name it, just look like it, and it will always identify you as a man who doesn’t have a clue about dressing well. Sure you’ve seen those ugly striped ties in multi colors and they’re just so plain ugly, I can’t even find words for it.
Instead, go with a tie that is silk, maybe wool, maybe cashmere, maybe some texture if it’s also going with the jacquard weave, or a print. Look for something more matte that is timeless that will stand the test of time and will always make you look dapper. Case in point, the tie I’m wearing here right now is vintage, I’ve had it for years it’s probably fifty years old but I can still wear it because it’s not shiny, it’s a classic small paisley pattern, and it just always looks dapper.
12 Essential Ties Every Man Should Invest In
11. Sports Sunglasses
Yes, you know what I’m talking about. Those mirrored sunglasses that you maybe wear when you’re outdoor, sometimes they have rainbow colors, and they’re just not something you should ever wear with a formal wardrobe in public. Instead, go with classic sunglasses; they’ve stood the test of time such as maybe a pair of aviators, maybe Wayfarers, or maybe you want to be like Steve McQueen, the king of cool.
12. Jerseys
By that, I mean sports jerseys that usually only wear if you go to a sporting event and you want to support your team, otherwise, they’re wholly inappropriate and just always make you look very immature. Instead, go with any other kind of shirts you can find but a jersey is just bad.
13. Slogan T-Shirts
They just make you look like a 13-year-old boy who wants to express himself but doesn’t know quite how and it’s not just immature but it makes people laugh about you and that you actually wear the shirt. I”ve seen men actually wear t-shirts that say douchebag or haters will always hate and while that may be the case, it’s just better to not wear it, plain or in bold colors on your shirt, but to write or talk to people in person.
14. Regular Neckties For Black Tie Events
You see it on the red carpet in Hollywood every year around the Oscars, and it’s just plain wrong. This is a formal dress code and it looks like you don’t know what you’re doing. I created a video about how to find the right black bow tie for your tuxedo on your situation.
The Ultimate Black Tie & Tuxedo Guide
15. Belt With A Vest
A vest should be either worn with just side adjusters or suspenders because a belt will create a gap between your waistband or your pants and your vest and it just looks unsightly. You should also never have a tie that peaks out underneath of it or maybe a shirt that pokes underneath of it when the vest is too short and the rise is too low because that simply shows that you don’t know what you’re doing.
16. Backpacks
I think only schoolboys should wear backpacks, otherwise, there’s no place for them in public unless you go hiking, or to an expedition where that’s kind of the only practical thing to carry, otherwise, with backpacks it’s very easy to hit people without even noticing it which is not just rude, but just not polite the same time, it makes you look like a schoolboy and you rather want to look like a grown man so get a leather satchel instead, a briefcase, maybe a canvas one, or something that suits your style, and leave the backpack with schoolboys.
17. Incorrectly Sized Ties
The problem is, they come underneath your jacket, and if you don’t wear a jacket, they even accentuate your balls which is just not where you want people to look at. Ideally, they look at your face and not at your crotch. Now, I get it, all the ties are too long and especially if you’re a shorter guy it’s very hard to find a tie that actually works for you because otherwise, you have this gigantic tie knot with your tiny head and it just looks goofy so instead, buy ties and the right length for you. I think we’re one of the only stores that offer the entire threefold classic neckwear range in short, regular, and long, so every man no matter the height can find a tie that works for him.
AVOID These Tie Knots if You Want to Look Stylish!
18. Large Armholes In A Suit / Jacket
Not only do they make you look like a football player, but they’re also uncomfortable and they restrict your movement. Instead, go with smaller armholes.
Learn all about the proper fit of a suit so you always look dapper!
19. Big Wristwatches
The 19th thing you should never wear as a self-respecting man are big, gaudy wristwatches that just scream for attention. I know they’re really popular these days but a smaller watch is just more sophisticated especially if it’s slimmer, and it serves the same purpose, and it’s just a hallmark of an elegant gentleman.
What are your style pet peeves? Share it with us in the comments!
Things Men Should Never Wear FAQ
What should a man never wear?
The usual offenders are sneakers with a suit, novelty or slogan t-shirts, cheap shiny ties, square-toed shoes, oversized tie knots, and anything with a loud logo. The thread running through all of them is the same: skip the gimmick and choose pieces made with care.
Can you wear sneakers with a suit?
It is best avoided. The dressed-up-but-casual sneaker-with-suit look is dated and unpolished. If you want comfort, a cushioned Chelsea boot or a loafer gives it to you without the compromise.
Are there items that stylish men disagree on?
Plenty. In our new video, two of us came to blows over crew-neck sweaters and Belgian loafers, with neither side giving an inch. Style has firm rules and genuine gray areas, and knowing the difference is half the skill.
What should I wear instead of cheap accessories?
Buy vintage. Belts, ties, cufflinks, and rings are where cheapness shows most, and the vintage market is full of well-made pieces at fair prices, far better than new, poorly made alternatives.
How do I know if an outfit looks like it is trying too hard?
Watch for the giveaways: an over-elaborate tie knot, loud designer logos, and too many statement pieces at once. Keep the knot classic, the branding quiet, and let the quality of the pieces carry the look.
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