How To Dress in Your 40s: A Men's Guide To Looking Sharp and Feeling Comfortable

In your 40s, time is precious.

No, we're not suggesting it's all downhill from here. That was your internal monologue speaking again. We're talking about all the stuff on your to-do list.

It could be your home life — pick up the kids, fix that leaking faucet, take out the trash, test how long you can relax on the couch before dozing off.

Or maybe you're the office alpha. To maintain that carefully cultivated position, you need to work as hard as the younger guys. Well … you should look like you're keeping up.

Either way, you probably haven't had much time to think about updating your wardrobe. 

If you want to stay looking sharp, we can help. Stick around for the next five minutes and you'll have a complete action plan for dressing better in your fifth decade.

The 40-something fashion blueprint

Here's the good news: Looking fly in your 40s isn't rocket science. 

Your mission is to land in the yawning chasm between an overgrown frat boy and a full-on grandpa. 

What does that mean in practice? Here's your step-by-step guide.

Step 1: Come to terms with your fashion failings

In most areas of your life, you've become much wiser with age (hopefully).

Your decision-making skills have improved, and you've collected enough "stories" to know which mistakes to avoid.

And yet, you're still wearing cargo shorts.

Look, you can put on whatever you want around the house. If all those pockets really make you more efficient at DIY, we're not going to stop you.

But if you're setting foot in the public domain, there's really no excuse.

The first step toward upgrading your fashion sense is to accept that some classics don't stand the test of time. Here are some items to leave behind:

• Cargo shorts: So bad, they need to be mentioned twice. Unless you're actively working on a construction site, these should remain out of sight.

• T-shirts with ancient cultural references: That slightly threadbare Blink-182 concert tee is a great souvenir, but it won't win you any style points.

• Anything that's too tight: Maybe all those washes have gradually shrunk your favorite shirt … or maybe your physique has "evolved" since you were 25.

• Oversized garments: For a brief period in your youth, wearing hoodies and jeans that were three sizes too big was fashionable. That time has passed.

• Beat-up sneakers: Great for mowing the lawn. Not so good for your fashion credentials.

These are just the worst offenders, of course. Take a look through your current wardrobe, and try to weed out anything that takes you back to the 1990s.

Step 2: Pick up some wardrobe essentials

After the clear-out, you might have some spaces to fill in your style roster.

In place of those unsightly artifacts, we'd recommend grabbing some versatile essentials. You know, items you're likely to wear more than once a year.

Here's a shopping list to get you started:

• A couple of quality button-downs: From relaxed drinks at the golf club to business casual events, these crisp shirts will serve you well in a variety of situations.

• A smart tee or three. A high-quality tee provides a simple foundation for many different styles, and it’s super comfortable as well.

• Performance tech pants in neutral colors: Jetsetter Tech Pants go with anything. They also have anti-ball-crush technology for all-day comfort — you won't see that in your ancient chinos.

• The intentional blazer: Something soft and neutral will impress your dinner date — without looking overly dressy for the post-match analysis at your favorite drinking spot.

• A smart casual sweater: Hoodies are for standing on the sidelines and walking the dog. For everything else, you need something with a little more sartorial elegance, like our Legacy Polo Sweater.

• Grown-up sneakers: By "grown-up" we don't mean grandpa's tennis shoes. You can wear a well-kept pair of sneakers in white or leather with a variety of outfits — just keep them clean, please.

Notice that we're mainly recommending neutral colors here. The idea is to build a solid style foundation, so you can add some razzle-dazzle on top. (Stay tuned for our verdict on vibrant colors and eye-catching patterns.)

Pay attention to fit and fabrics

As you build your new wardrobe, we can't stress this enough: Focus on fit and fabrics.

Fit makes a huge difference to how "put together" you look.

A shirt that flaps off your shoulders and hugs your gut is never going to look good. In contrast, a tailored shirt can really enhance your physique.

We'd also recommend investing in high-quality fabrics. Yes, that's going to cost you a little more now. But well-made garments look better and last longer — which means spending less of your future life shopping for clothes.

Even Warren Buffett would be proud of that return on investment. 

Step 3: Add your own style (in moderation)

Given the choice, you'd probably be rocking a Hawaiian shirt at every backyard BBQ and a "jazzy" tie at every work event.

Feeling that comfortable in your own skin is great. We applaud you.

But maybe you could redirect that energy into something more … tasteful? Stylish? Forgiving on our retinas? 

Let's look at how you can start turning heads for the right reasons.

Choose your colors carefully

Guys often veer toward one extreme (boring blacks and grays) or the other (garish) when it comes to clothing colors. 

To avoid both pitfalls:

• Choose subtle colors for sophistication: You don't need to be a walking peacock to impress. An array of subtle colors should attract plenty of admiring glances.

• Navy blue is your friend: It's smart but not too serious.

• Consider your skin tone: Contrast is always a winner here. Lighter skin tones go nicely with dark blues and greens, while darker skin matches well with lighter creams and yellows.

• Stay away from neon: These colors are made for high-viz jackets, not your weekend brunch outfit.

• Use black with caution: It can look smart. It can also seem overpowering. For non-formal outfits, consider something softer like dark gray or charcoal.

Embrace subtle textures and patterns

You don't have to use dazzling hues to elevate your look.

Try swapping solid colors for refined textures. Herringbone, micro-checks, and subtle weaves add interest without screaming, "Look at me."

You could also introduce patterns with an eye-catching pair of socks or a flashy jacket lining.

Just make sure you don't overdo it — no more than one or two fancy patterns in a single outfit.

Add a few choice accessories

They might not take center stage, but accessories can make all the difference to your outfit — like the garnish on your fancy restaurant dinner.

Here are some options to try:

• A classic watch: A good timepiece is (ironically) timeless.

• A leather belt: If you're dressing up, choose a tone that matches your shoes.

• Minimalist sunglasses: Avoid frames that'd look at home in an ‘80s music video.

• A simple, quality wallet: Fill it with the essentials, but no one wants a bulge.

• A leather messenger bag or sleek backpack: This really turns up the style.

Step 4: Dress for the occasion

You now have all the ingredients for effortless style. You just need to put them together in the right order.

Not sure where to start? Next up are some examples of how to dress for various occasions.

The backyard BBQ host

You’re manning the grill, chatting with neighbors, and somehow also handling playlist duties. This outfit will keep you cool, comfortable, and casually iconic.

• Top: Breathable Anytime Tech Tee in a Deep Blue or Olive Green. Sling on a sweater if you misread the forecast.

• Bottom: Slim Fit Jetsetter Tech Pants in a neutral color like Sand Stone or Ice Gray. For warmer weather, grab some Jetsetter Tech Shorts.

• Shoes: Fresh, minimalist leather sneakers (white or tan).

• Accessories: Aviator sunglasses and a classic canvas-strap watch.

The conference room hero

Your work clothes aren't just for work — they need to look at home when you hit happy hour. This outfit should cover both bases.

• Top: Tailored Oxford shirt (light blue or micro-check) with sleeves you can roll up.

• Bottom: Jetsetter Tech Pants in Charcoal Gray or Bering Sea (limited edition alert).

• Shoes: Polished brown leather loafers.

• Accessories: Slim leather belt that matches your loafers, and an understated watch. Add a leather briefcase or laptop bag to pretend you're an executive.

The Sunday stroller

This look is perfect for visiting the museum, a casual brunch, or dispersing your kids’ energy at the park. Standard pre-game Sunday stuff.

• Top: Lightweight quarter-zip merino sweater in a subtle pattern or solid earth tone.

• Bottom: Classic dark-wash jeans with a modern, straight-leg fit.

• Shoes: Suede Chelsea boots (medium brown or taupe).

• Accessories: Sleek sunglasses in summer, or a textured beanie in the cold season. Add a casual canvas messenger bag if you're carrying your kids' clothes.

The stylish dinner date

Whether you're happily married or trying to embrace your silver fox age, this outfit should impress your date and keep you sufficiently comfortable to make light conversation.

• Top: Button-up shirt in a muted print (think understated dot or micro-floral). Roll your sleeves if you're feeling risqué. 

• Bottom: Slim Fit Jetsetter Tech Pants in Space Black or Olive Green.

• Shoes: Sharp black or cognac Derbies.

• Accessories: Leather strap dress watch. Add an optional blazer for instant polish.

The wedding wingman 

You're not the star of the show, but damn if you aren't the best supporting actor. Here's how to look wedding-worthy without being that try-hard guy at table nine.

• Top: Tailored navy suit with subtle texture, crisp white dress shirt, and burgundy grenadine tie.

• Bottom: Navy suit trousers with perfect break (i.e. they should just reach your shoes).

• Shoes: Dark brown polished cap-toe Oxfords.

• Accessories: White pocket square with minimal fold and a dress watch with leather strap.

Here's to your most stylish decade yet

Hitting your 40s doesn't mean being consigned to the fashion wasteland of middle age. 

Sure, you should embrace your maturity. But there's plenty of scope for some youthful style in your wardrobe. 

Keep it classy, and you're on to a winner.

Want to upgrade your wardrobe instantly? Our store is packed full of high-quality essentials, from our Jetsetter Tech Pants to our new Tech Polo. Go take a look around!