40 Best Tips For Dressing Well in Your 40s

1 | Skip cargo shorts. Or pants. Or cargo anything.

Cool in college, straight-up uncomfortable in your 40s. And, yes, guys: Cargos are definitely on the list of 38 Things No Man Over 40 Should Ever Wear. 

2 | Avoid the matchy-matchy look and embrace separates.

A two-piece suit feels so stiff on women, especially if you're a little bit older. Instead, if you're dressing for work, try mixing blouses and sweaters with skirts or trousers instead. And for more great advice, know the 50 Things No Woman Over 40 Should Own. 

3 | Your white tees should be crisp—no holes, stains, or shreds.

Time to toss those Hanes. Bonus points if you go all the way and opt for a crisp white polo.

4 | Skip out on super-cheap fabrics.

Fast fashion may look cute, but that's about where it ends—in your 40s, steer clear of cheap fabrics and gaudy styles. It's far classier to have an edited rotation of investment pieces. And for more great advice for aging gracefully—and intelligently—check out the 40 Best Hobbies to Take Up in Your 40s. 

5 | Pass on the Canadian tuxedo.

Denim on denim is literally always a no for men, especially after you turn 40. You should know better by now. Remember: Looking your absolute best is a must if you want to really conquer your 40s. 

6 | Balance proportions.

Now that you've got a rotation of tops and bottoms on lock (see #4), make sure you balance out your wardrobe. A flowy blouse looks great with a form-fitting pencil skirt, but it looks rather sloppy when paired with oversized, loose trousers. It's like the branches of government: There always needs to be a balance of power.

7 | Hang up your sports jerseys.

Don't care if it's Game Day. You don't need the jersey. This especially goes for the 30 Ugliest Sports Uniforms Ever Designed. 

8 | Bid adieu to Daisy Dukes and micro miniskirts.

You could have the best legs in the world and you should still keep uber-short hemlines, like the ones on Daisy Dukes and miniskirts, on their shelves and hangers. We're not saying you shouldn't show some skin—just make sure that some things are left to the imagination.

9 | Never wear shiny black shoes with denim.

Shiny black shoes are a must for men in their 40s: You're definitely going to attend at least a few super-fancy events, and god knows you've got more than one gray suit by now. But don't wear those wingtips on date night with your Levis—you'll look like a guy on a business trip who forgot his other pairs of shoes.

10 | Ripped and shredded denim should be left behind.

A little shred here or there? Stylish. Majorly ripped, oversized holes? Unnecessary—and far from stylish. Besides, why would you want to wear a pair that's one tear away from completely falling apart?

11 | Opt for less chest with your V-necks—or skip 'em altogether.

When in doubt, skip the V-neck: No one wants to know how much (or how little) chest hair you have. Instead, opt for The One White T-Shirt Every Guy Needs to Own. 

12 | Invest in a beautiful, classic coat that works for your climate.

One that works almost everywhere is an iconic camel trench. But make sure to find the perfect coat you—after all, it's going to be a big investment, and chances are you're going to wear it everywhere.

13 | Tailor a few pairs of trousers to your ankles.

You probably notice the younger men at the office wearing suit pants un-tailored and thus too long. They look like a mess, with puddles of fabric at their feet. You're better than that. So try bringing a few pairs of pants up an inch or two, and you'll have a sleeker-looking physique that's clean-cut, too.

14 | Splurge on a little black dress.

Jewel tones are gorgeous, but a shiny, inky little black dress will really work in a variety of settings. And since it's such a neutral hue, you'll be able to style it a slew of ways and with a ton of a accessories, giving you a ton of wear miles out of just one dress.

15 | Jewelry should be kept simple, minimal, and personal.

This dude has far too much. He looks like he belongs on a college campus—and not in that athletic, fresh way. Stick to a classic ring and an iconic watch and nothing more. And to channel your inner Steve McQueen, here are 7 Must-Have New Vintage-Inspired Watches. 

16 | Play with high-low styling.

Just because you shouldn't buy your little black dress from a store designed for those who are, let's say, 21, doesn't mean you can't pick up some cool extras there. In fact, that's the way most celebrity stylists create their best looks: when they play with a high-low mix.

17 | Skip anything embellished, including concert tees.

I have no idea where this guy is going, but I'd advise not going with him.

18 | Wear hem skirts just to or above the knee.

It's just the right amount of skin. Period.

19 | Invest in quality sunglasses.

Great frames for the gorgeous window to your soul.

20 | Same for you, ladies.

See above.

21 | Got loafers? Try sporting 'em sockless in warmer weather.

On younger men, this can look a bit precocious, but by the time you're in your 40s, you have the full right to rock your loafers without socks, especially in warmer weather. It's the ultimate in country-club cool, and it qualifies as one of the Definitive Style Rules for Men Over 40. 

22 | Get fitted for fresh bras and undergarments.

It's important to refresh your lingerie drawer frequently, but when it comes to dressing well in your 40s, it's really all about that foundation. That starts with your undergarments. By your fifth decade, you're ready to have yours picked out by a pro.

23 | Embrace suits with mixed patterns.

Hawaiian shirts? Nah. But subtle dots and pinstripes? Absolutely. When suited up, mixing small, delicate patterns packs a seriously stylish punch without being over-the-top in any way. Take it from us: A non-boring suit is guaranteed to energize your day. 

24 | Reach for darker shades of denim.

Being in your 40s doesn't require you to get rid of your entire jeans drawer. Instead, opt for a classic cut—think straight or bootleg, or both—in a darker, indigo stone wash without any rips or tears.

25 | Embrace a mix-and-match philosophy when it comes to your shoes and belt.

See that Canadian tux? That's a hard no. The mismatched shoe and belt? A pass go.

26 | Embrace lash extensions.

Pare down your makeup and get some lash extensions at the same time. The extensions will make you feel instantly more elegant and gorgeous, which will translate to your head-to-toe look, too.

27 | Only purchase clothing that makes you feel amazing.

Ladies know this, but men, this is your formal announcement: DON'T BUY ANYTHING UNLESS IT MAKES YOU FEEL AMAZING. Otherwise, you just don't need it.

28 | Keep your number of accessories limited, depending on their size and visibility.

Two or three strategically curated accessories—say, a belt, bracelet, and stud earrings—can take a boring outfit and make it incredibly stylish. Piling on like, ten, though? Not as much.

29 | Invest in your actual closet.

Buy wooden coat hangers, fabric suit bags, and plastic boxes for your shoes. The more organized you are and negative space you create, the neater it'll be and the more clear-headed you'll feel. Swear.

30 | Splurge on basics, like white tees and classic, neutral sweaters.

In the same way you shouldn't waste money on cheap fabrics, you should spend you money on the things you'll wear over and over again, just like that shiny new little black dress. Think: High-quality, impeccably fitting white tees and timeless, crewneck cashmere sweaters.

31 | Get all of your measurements taken again.

The ladies get it done, and men should, too. Odds are your suit doesn't fit the way it did five, or ten, or fifteen years ago. No judgment.

32 | Forget about flip-flops and stilettos: Find balance in your footwear instead.

The best shoes have a small heel, which provides your foot with support but doesn't require any kind of balancing skills. Ballet slippers, like the ones pictured here, look equally as chic when styled with denim or cropped pants as they do with that little black dress, of course.

33 | Accessorize with a matching suite of luggage.

As you travel more in your 40s, make you trip that much more stylish with a suite of matching luggage. Hard-top spinners will product even the most delicate tech gadgets while stowing sweaters, socks, and sneakers efficiently, too.

34 | Need bifocals? Make sure the lenses are mounted and shaped accordingly.

Oversized, super-thick lenses are not only outdated, but will make you feel outdated, too. If you need readers, make sure your optometrist uses newer technology to cut sleek lenses that fit into your frames flawlessly.

35 | Invest in your loungewear for your time at home.

Why? Because you've earned a better way to end your day than lying around in your boxers.

36 | Layers upon layers upon layers.

Women's body temperatures tend to fluctuate more easily than men's, which is why it's so important to layer your clothing, especially in seasons when the temperature drops a significant amount after the sun sets. It's one of the more practical strategies for how to dress over 40.

37 | Be wary of where you wear your gym gear.

Besides the fact that you should be shopping at places like Lululemon for cool men's workout wear, save your exercise gear for the gym and only the gym. You're not on the high-school basketball team, you know?

38 | Swap your old leggings for a pair of 7/8th's.

These guys just have a slightly different cut—they're a flattering, cropped at a length that sits just on the calves above the ankle—and look even better if you pair 'em with cool sneakers and no-show socks. They're also just very right now, too.

39 | Get your grooming routine on lock.

If you thought you could learn how to dress over 40 without some grooming, you're out of luck. One of the best tips for dressing well in your 40s is to have a clean-shaven, well-groomed look. Because even if you're wearing rags, you'll still look fresh to death, you know?

40 | Aim to ultimately create a capsule wardrobe.

After you've bought your splurge investment pieces and basics, your well-curated wardrobe deserves to be coordinated for endless mix-and-match opportunities, especially when you embrace the high-low styling tricks and accessory rules suggested. Because the amount of looks is truly endless.

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