The 20 Definitive Style Rules for Men Over 40

Cargo shorts need not apply.

The 20 Definitive Style Rules for Men Over 40

Cargo shorts need not apply.

A lot of things happen when you get north of 40 years in age. For starters, you find yourself worrying less and less about the little stuff, you discover that the people around you respect you a whole lot more, and your yearly physicals all of a sudden get way more intrusive. But another thing happens, too, which no one actually stops to tell you about: you’re no longer allowed to wear tank tops.

It’s true. Also: no more cargo pants. And those space age-looking pair of Lebrons you wear around the house? Get rid of them, buddy.

Watch Now: The 7 Essential Skills Every Man in His 40s Knows.

 

A man over 40 has certain responsibilities in this life—and they extend to his wardrobe, as well. The only problem is that they’re not always so obvious. Can you wear sandals? (Actually, yes.) What about a deep v-neck tee? (No.) So we’ve taken the liberty of outlining everything you need to know about dressing your dignified age and always looking your best for any occasion. And while you’re polishing up your look, don’t forget to check out our roundup of the Best and Worst Haircuts for Men in Their 40s.

1
Never wear cargo shorts. Or pants. Ever.

We know this is obvious, but it bears repeating: no cargos. Ever.

We know they’re comfortable and even convenient—yes, all those pockets can come in handy—but there’s nothing that screams “I’m an out-of-touch dad” louder than these ghastly bottoms. And for more suggestions on things to erase from your life, don’t miss the 40 Things to Let Go of in Your 40s.

2
Wear White Tees. But They Need to Be Crisp.

Try not to wear a white t-shirt by itself unless it’s in absolutely pristine condition. (Meaning: cleaned, ironed, and folded.) Otherwise, you risk looking like you just rolled out of bed. Trust us: while this is a really cool look if you’re a young drummer in a band, it’s not suitable for a dignified older man. And if you need to boost your shirt collection, here are the some of the best new shirts for work.

3
You Need to Have a Good Tailor in Your Rolodex.

Some men are lucky enough to fit effortlessly into store-bought suits with no adjustment needed, but those guys are rare. Do yourself a favor and make the extra effort to get your pants and suits cuffed and hemmed appropriately—because ill-fitting clothes are the surefire sign that you don’t have your act together. Also, if you ever want to dress like a multimillionaire, you’ll need your clothes to fit just right.

4
Never do denim on denim.

Yes, this is another great look on young hipsters, but once you hit 40, it’s basically impossible to wear clothing with a sense irony. Our advice? Don’t try. If you want to wear jeans, opt for a casual button down or simple tee on top. Denim and chambray shirts work best mixed with tan or brown chinos, and denim jackets should not be worn with any other blue jean pieces. Speaking of: don’t have any great chinos or chambray shirts? We suggest you read the 15 Items Every Man Should Have in His Closet.

5
Keep Your Sneakers Plain and Classy.

Yes, you can absolutely wear sneakers—even with business casual clothes. They complete any weekend look and give off a cool vibe without trying too hard. If you don’t have any, invest in a classic starter pair in all white from Adidas, Nike, or New Balance. But it should go without saying that you should eschew any neon colors, black shoes paired with blue denim, and any styles with a decidedly orthopedic vibe. We recommend these pairs, which are popular among the most stylish NBA superstars.

6
Save Sports Jerseys for Sporting Events.

Unless you’re headed to a game (or you’re hanging out on your couch watching one), skip the whole jersey look. It doesn’t matter how rare or limited-edition they are, jerseys look bad with virtually everything, and they tend to employ horribly unflattering color schemes. Another sport clothing category never to be worn unless you’re headed sweat sessions? Cycling garb. Any shirt that zips up does not qualify as a real shirt.

7
Never Wear Shiny Shoes with Jeans.

This is an error so common among dads that we feel the need to speak up.

Fact: ultra fancy shoes—the kind you get shined and wear with your best suit—should never be worn with a pair of jeans. For someone who has reached a point in his life when he knows his own style, this sort of “high-low” visual cacophony sends all of the wrong messages. If you’re not sure what shoes to wear with your jeans, here you go: sneakers, casual loafers, and even boots are all safe bets.

8
Always Wear a Real Watch.

Yes, you can use a tracker when you head out to log some miles or hit the gym, but you should never wear a digital watch. Instead, invest in a classic analog timepiece that’ll look as great with casual wear as it does with a suit. For inspiration, here are 8 Handmade Watches That Double as Works of Art.

9
Only Wear Low-Key Pleats.

To pleat or not to pleat?

Well, when it comes to pants, it really is a matter of personal preference. But unless you’re committing to the ultra trendy baggy pants look (you shouldn’t), it’s safest to stick with just one pleat per leg in order to give the illusion of a more streamlined silhouette. For more on the looser-trousers trend, be sure to read Should You Wear Baggy Jeans? 7 Style Savvy Women Weigh In.

10
Never Show Too Much Chest.

Though showing off your pecs can be tempting, the time for man-cleavage has passed. We’re not saying you can’t undo the first couple buttons of your shirt when you’re on vacation, but we are saying: Don’t dress like Fabio. In short, don’t undo your shirt past the second button, and say no to deep v-neck t-shirts.

11
Flash Some Ankle Whenever You Can.

Now, this isn’t permission to wear capris, but a slightly shorter cuff is totally acceptable in casual pants for older guys, especially if you’re going for a great loafers-with-no-socks look. A good guideline is that your pants should be hemmed or cuffed to two fingers’ width above your ankle bone. When in doubt, a tailor can show you the difference between “cool” short and “awkward” short.

12
Wear Very Little Jewelry.

Beyond a watch and wedding ring, jewelry for men is semi-controversial. While some guys won’t go near any bling, others like to incorporate class rings, religious pieces, subtle beaded bracelets, and even sentimental family heirlooms into their everyday outfits. Here’s the deal: it’s not that you should never wear jewelry, but as a guy in your 40s, you should keep it toned down. (Yes, a neck full of chains will make you look like a mob boss.) If you want to wear some jewelry, a good rule of thumb is to keep it to just one piece beyond your watch and wedding ring.

13
Banish embellished tees forever.

No t-shirts—or anything else, for that matter—with swirly type emblazoned across the chest. The same goes for rhinestones, patches, or ostentatious graphics.

14
Embrace Cooler Sunglasses.

Sunglasses are one of the few accessories that are completely ageless, so if you’ve always wanted a pair of funky acetate shades or horn-rimmed specs, consider this permission to buy them. The only ones to avoid are overly sporty sunglasses. If you can imagine a professional cyclist wearing them, they’re a no-go. Here are some great shades to buy right now.

15
Go Sockless with Loafers.

Certain shoes always look better older men without socks, and that includes driving shoes and casual loafers. Dress shoes, on the other hand, should always be worn with dress socks. And speaking of…

16
Never Wear Athletic Socks with Dress Shoes.

Don’t wear crew-cut cotton socks with anything other than sneakers. Speaking of: if you’re looking for a great pair of kicks, here are the High-End Sneakers That’ll Floor Everyone.

17
Mix Patterns Only with Suits.

A shirt with pinstripes mixed with a tie featuring a small-scale geometric print can look really sophisticated under a well-fitting suit. You can even wear a suit with a subtle pattern over a shirt with a geometric or check pattern. But let’s be clear: the time is over for mixing patterned pieces in casual wear. All that crazy clashing? Leave it to the youngsters.

18
You Need a Barber Who Knows Your Name.

At this point in your life, you need a barber or hairstylist you know and trust. You want someone who you know can keep you looking distinguished and handsome, not trendy and adventurous. Plus, the time has passed when scruffy was a cute look, and now skipping a haircut will just make you seem sloppy. A standing appointment every two to six weeks—depending on your hairstyle—is not only a necessity, but it’s also built-in “me” time.

19
Don’t always match your belt and your shoes.

Truth: you really don’t have to worry about whether your accessories are all perfectly coordinating anymore. The matchy-matchy look is actually a bit outdated, and being too put together can make you look stuffy and uncool—exactly what you want to avoid. That being said, you should go for a contrast that looks intentional, like brown shoes and a tan belt, rather than one that just looks like you can’t match. Need some great recs for new kicks? Here are the 10 Best Suiting Shoes on the Market Right Now.

20
Wear what you feel good in.

The most important factor in pulling off any look? Confidence. If you feel great in bright colors, edgier prints, and flashy fabrics, don’t let us discourage you. At the same time, if you feel dignified and sophisticated in mostly neutrals, stick with what you love. The pieces you feel the best in are the ones that will portray you—and everything you have to offer—in the best light. Only then can you start having the best decade of your life.

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