40 Common Style Tips Men Should Always Ignore

Some rules are just meant to be broken.

40 Common Style Tips Men Should Always Ignore
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If you’re a man, you’re well aware of the fact that there are roughly 4,293,091 “style rules” online telling you how and how not to dress. Don’t mix black and brown! Always tuck in your shirt! Never wear white after Labor Day!

But guess what? Many of them are totally bogus! To learn the ones you should always brush aside when you want to up your style game and look your very best, read on. And for more amazing style tips for upgrading your look, check out these 50 Essential Accessories for Men.

man wearing a white tee shirt and white pants

1
Don’t wear white after Labor Day

This age-old fashion “faux pas” couldn’t be more passé. Its origins date back to the late 19th century, when white was the choice color among wealthy summer vacationers. When fall rolled around, they’d ditch the white for darker clothing more fit for the workplace, to signify a “get back to work” attitude. (The soot-heavy industrial environment at the time wasn’t exactly friendly to white linens, and darker clothing masked any stains.) Next time the fashion police try to scold you for running afoul of this rule, kindly point out the fact that your office is spotless—and carry on your way. And for more sage fashion advice, check out these 20 Men’s Style Trends You Should Actually Try in 2019.

man putting on converse shoes while wearing a suit

2
Don’t wear sneakers with dress pants

In the event you haven’t paid a lick of attention to menswear in the past, oh, decade or so, sneakers are cool now. Like, really cool. They’re not reserved for athletes and tired dads any more. If you want to wear sneakers with slacks (or even a full suit!), don’t let anyone stop you. In fact, a nice pair of sneakers—like, say, this deliciously textured leather pair from Common Projects ($450)—beats the stuffing out of a meh pair of Oxfords any day.

man wearing socks and sandals at night

3
Don’t wear socks with sandals

Yes, discretion should always be used whenever you choose to wear sandals outside of a pool or beach setting. But if you style the look right, the combo can come off quite fashionably—as long as the rest of your outfit is on-point. Oh, and for the love of all that is holy: stay away from the flip-flops! And for more ways to look great, check out these 15 Killer Style Accessories You Never Knew You Needed.

man wearing plaid blazer black pants and brown shoes

4
Don’t wear brown and black at the same time

It’s a rule as old as time. So, yeah, it makes sense that it’s outdated by now. There’s no reason to limit your color options, especially considering black and brown can look amazing together. The key, as with all things, is to keep it simple: no bright colors, no fancy bells and whistles, no more than one pattern (and a minimal one, at that). Otherwise, you’re doing too much. Mixing black and brown is itself a statement.

5
Socks should match your trousers or your shoes

Leave this rule to the hardcore suit traditionalists. With so many fun sock options on the market, why stick to the same-old-same-old? Footwear is the quickest and easiest place you can score some style points, and that applies to your base layer as well. For ideas, take cues from stylish sock maestro Justin Trudeau.

man buttoning a white french cuff shirt

6
Jackets should always be worn with French cuff shirts

French cuff shirts don’t always have to be worn so formally. Often, they work just as well (if not better) with casual looks. For maximum laissez-faire attitude, pair with a leather-strap chronograph and some dark-wash denim.

man wearing an untucked dress shirt

7
Dress shirts should always be tucked in

Menswear is more diverse than it’s ever been, and guys have become way more creative in the way they style themselves. Dress shirts don’t always have to be so stuffy; the fashion set have been spotted wearing them untucked, and even a bit oversized, for an edgier, more relaxed fit. For ideas on what to rock, check out The 10 Best Button-Down Shirts You Can Wear Untucked.

8
Always wear a belt if your pants have belt loops

We’re not sure who minted this rule, but whoever it was, they clearly took things a bit too literally. The fact is: A belt-free pant is a happy pant. If your pants stay up no problem without a belt, that means your look is tailoring to perfection—a sign of high-level style. (Of course, don’t be discouraged from wearing one if you want to. Personal preference is always key!)

Looking at watch

9
Silver and gold should never mix

This is another common “rule” that really just comes down to personal preference. Silver and gold can definitely live together harmoniously. Just don’t overthink it. To wade into the look, pair your go-to watch with one of these 7 Cool Cuff Bracelets You’ll Wear With Confidence.

man shopping for shirts and suits in a clothing store

10
Expensive means better

Every savvy shopper knows how false this pretentious sentiment is. We’re not living in feudal times anymore; there are countless affordable, high-quality clothing brands out there. For instance: these 40 Best Style Brands for Men Over 40.

smart word

11
Your belt should always match your shoes

Did your grandpa teach you this rule? Yeah. Thought so.

dressing well in your 30s

12
Always wear socks with pants

It’s practically sacrilege for dudes to stroll through the world sans socks. But that’s a rule you should reconsider. If you take it from this diatribe at The Cut, going sock-free is about the sexiest thing a guy can do (come summertime, that is).

men wearing pleated pants at duckie brown fashion show

13
Never wear pleated pants

Pleated pants have sparked endless debate in the menswear community over the years, though it’s not exactly clear why. Yes, they’re a bit of a throwback—but retro is totally en vogue. Plus, runway shows from recent seasons have put pleated pants front-and-center, so they’re about to be everywhere soon. Stay ahead of trend and pick up a pair (or three) now. Consider a pair with a mild pleat, like this wool-blend option from Reiss ($220).

suspenders and belt is not a good work look

14
Never wear belt and suspenders at the same time

They both serve the same purpose: to keep your pants. So, yes, technically, you really only need to wear one. But if you want to wear both—as long as it’s in the name of looks and not practicality—go for it. What’s the worst that could happen?

Tom Ford

15
Don’t unbutton more than two buttons

Be wary when it comes to breaking this rule, since an overly unbuttoned shirt can quickly veer into sleazy territory. However, if the mood and occasion permit, there’s no reason why letting loose with an extra button can’t be done. Take your cues from Tom Ford, the classiest 21st-century Lothario. Make sure your shirt has a high, strong collar. Don’t unbutton below the naval. And never go without the power suit.

a closeup shot of a deep red jacket paired with a white shirt and a floral tie and pocket square

16
Your tie and pocket square shouldn’t be the same color

Though varying your tie and pocket square colors is a tried-and-true way to add flashy contrast to any look, matching them is a tried-and-true way to keep your look cohesive. And making them match doesn’t mean you can’t have fun! Go for stripes, polka dots, or even florals.

man wearing a suit at a bar

17
Don’t overdress

Best Life rule of thumb: It’s impossible for a guy to be “overdressed.”

jeff goldblum

18
Dress your age

Surely you’re familiar with expressions like “Age isn’t anything but a number,” or “You’re only as old as you feel.” Well, the saying can also apply to fashion. If you’re at the intern stage but want to rock a three-piece or a sweater vest, go for it! If you’re up there in years but feel like trying out “younger” clothing (lacquered leather bombers, punk-rock Chelsea boots, ostentatiously patterned shirts), make like Jeff Goldblum (age: 66) and do exactly that. There’s no reason age should determine the clothes you’re supposed to wear.

Nike Cortez shoes, great for low-maintenance upgrades

19
Always go with a brand name

Brand names aren’t always synonymous with stylish. You can certainly stay up-to-date with the latest threads without splurging on pricey designer labels. All it takes is a little bargain hunting and some good taste.

watch

20
Watches are a guy’s most valuable accessory

Thanks to smartphones, watches are no longer a necessity; anyone who wears one is wearing one purely for looks. So don’t sweat it if timepieces aren’t your thing. No one really cares whether or not you’re wearing a Rolex nowadays anyways.

man wearing a hoodie underneath a leather jacket

21
Hoodies should only be worn during casual occasions

Thanks to leading fashion mainstays—such as Balenciaga, Gucci, and Off-White—hoodies have become a go-to for many trendsetters. Worn under a blazer, pea coat, topcoat, leather jacket, suede bombes, or even on its lonesome, there are countless ways to style this once-gym-only staple, making it a suitable option for any occasion.

barack obama and joe biden on the campaign stump

22
Rolled up sleeves look sloppy

Stodgy style aficionados say it looks messy. But that couldn’t be further from the case. It’s even a look former president Barack Obama, a fashionable statesman if there ever were one, has rocked on the stump for years.

23
Shave every day

Clean-shaven isn’t the only option for keeping dapper. There are approximately 482,109,248 ways to wear facial hair (so long as its properly styled). Long beards are still a bit taboo, unfortunately, unless you’re chopping wood or digging for treasure or living in Brooklyn.

dressing well in your 40s

24
Never wear head-to-toe denim

Ah, the “Canadian tuxedo.” It’s been parodied and pilloried for years, thanks in part to that infamous matching early 2000s red carpet ensemble rocked by Justin Timberlake and Britney Spears. But don’t let that prevent you from giving the two-piece denim look a try. You’ll be surprised at how stylish it can be. (Just be sure to skip the cowboy hat—that’s never coming back.)

justin theroux

25
Never wear all black

Anna Wintour, fashion’s fairy godmother—and the woman behind The Met Gala, the best-dressed night of the year—famously dubbed head-to-toe black as one of her biggest style pet peeves. But the fact of the matter is, simply, that black is one of the most reliable colors out there; an all-black look is effortlessly chic, even when worn casually. Small wonder Justin Theroux, one of the world’s most indisputably attractive men (c’mon: he dated Jennifer Aniston!), regularly goes with all-black looks, both on and off the red carpet.

dressing well 50s

26
Only wear solid color ties

There’s no shortage of fun ties on the market. Why limit yourself to a solid? Live a little. For inspiration, check out the 10 Best Knit Ties on the Planet.

man wearing a red blazer and plaid pants

27
Pocket squares are essential

In tandem with the casualization of the American workplace, the prevalence of the pocket square has experienced a precipitous decline. Sure, wearing one is a fun way to liven up a look—and, if you’re going tie-free, it looks amazing—but to call it mandatory is a bit excessive.

man wearing a black topcoat and a bright red vest

28
Avoid bright colors in winter

This goes right up there with the silly “Don’t wear white after Labor Day” rule. Winter is dark and depressing enough. Why carry the gloominess over to your clothing? And if you’re on the slopes (or engaging in any outdoors activity, really), wearing a bright color is a safety move: you’ll be easy to spot (and look great, too).

tailor secrets, essential dating tips for men over 40

29
Get rid of clothes you haven’t worn in over a year

Fashion is a cyclical business; you never know what may come back in style in a few years’ time. If you’re on the fence about tossing something out, keep it for just a little while longer. Remember: it’s better to have something and not want it than to want something and not have it.

30
Stick to the trends

A lot of guys use “fashion” and “style” interchangeably, but the two words couldn’t be more different. Fashion is all about what’s new and what’s next—the latest trends, the buzziest designers, the hottest collections—and it can honestly get a little ridiculous. Style, on the other hand, is all about looking fantastic, no matter what, like the clothes you wear are a natural extension of your being. Stay up to date on trends if you wish. But your sartorial lodestar should always be having good style.

style tips

31
Avoid graphic T-shirts

Graphic tees will never go out of style—you just have to choose them wisely. It’s never a bad idea to have a few in stock to add some variety to your wardrobe.

man wearing a striped tie and a plaid jacket

32
Don’t mix plaids with stripes

This one’s risky, but cross-pollinating varying patterns can prove quite interesting. Do so modestly, though. Make sure you choose muted, reserved options—or you’ll find disciples of the rule wagging their fingers in disapproval.

man wearing a tan suit and a purple tie

33
Always keep a suit jacket buttoned

An unbuttoned suit jacket is a very liberating feeling. Try it sometime.

man wearing a double-breasted jacket

34
Double-breasted jackets should only be worn during formal occasions

Time was, you could only wear double-breasted jackets during high-stakes meetings and highfalutin events. But no longer! For a casual look, ditch the full suit and pair a double-breasted blazer with a pair of sharp slacks or dark denim.

man wearing light wash denim

35
Dark wash denim is always better

A few years back, it seemed as if the fashion community collectively deemed deep indigo denim as the only acceptable hue. And sure, we love a good dark wash. But a lighter pair of jeans works just as well, and can even make the rest of your outfit pop. Just please leave the acid wash where it belongs: in the ’90s.

men in suits at milan fashion week

36
Keep it minimal

Minimalism is usually safer when it comes to fashion, but there’s no shame in being adventurous with bolder pieces from time to time. How boring would it be if people didn’t take risks with their style?

dressing well in your 50s

37
Always shine your shoes

Spit-polishing your shoes to mirror-grade is all well and good. But some shoes—namely, sneakers and leather boots—get their character after they’ve been worn (and beat up) a few times.

Jersey Classic 80s Jokes

38
Slimmer is better

No. Wearing clothes that suit your body type is key. If you’re uncomfortable in tighter clothes, chances are they’re not meant for your shape. Don’t feel ashamed in sizing up.

style tips

39
Avoid square-toe shoes

Square-toe shoes have gotten a bad rep over the years, but rest assured, their comeback has been completely embraced by the fashion community. Calvin Klein, Gucci and Balenciaga have all crafted square-toe footwear in recent seasons, and they actually look very stylish.

man wearing a blue blazer and dark jeans holding a smartphone and talking a selfie

40
Don’t wear denim with blazers

Like salt and pepper, ice cream and fudge, Simon & Garfunkel, denim and blazers have a perfect synergy. One is laid-back and casual; the other is polished and sophisticated. Put them together and you’ve got a look that’s both relaxed and smart. And who doesn’t want that? And if you really want to kick your look up a notch, check out these 20 Easy Ways to Elevate Your Style Game Instantly.

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