How To Dress in Your 30s: A Men's Guide To Leveling Up Your Wardrobe

May 19, 2025Rebecca Traverzo

Being a 30-something man, it’s sometimes hard to know where you stand.

You still feel young enough to play professional sports (“If only I’d practiced as much as these guys…”). But your hairline tells a different story.

You’re probably more comfortable in your own skin than ever before. And that’s important, because kids will destroy you for attempting the latest trends.

You also probably have more responsibilities now. At least they come with a bigger paycheck or more likable expenses (AKA the kids).

Finding your way is no easy task — especially in fashion terms.

To help you walk the fine line between college sophomore and full grandpa status, we created this step-by-step guide.

Here's how to dress in your thirties.

Step 1: Purge your wardrobe

Goodbyes are never easy. But now that you're a grown man, it's time to bid adieu to some fashion favorites from your younger years.

Not sure where to start? Here's the hall of shame:

Graphic tees with cultural references that are lost in time.
Oversized hoodies from your college days.
Cargo shorts — these were always a bad idea.
Basketball shorts for anything other than basketball.
Those beat-up sneakers that have seen more miles than a Greyhound bus.

None of these garments should be anywhere near your wardrobe from now on.

Step 2: Build a solid style foundation

You don't actually need that many clothes to look good. (Hear that? It was your wallet sighing with relief.)

In your thirties, you can build your entire personal style around a few key items:

All-day, every day pants: Our Jetsetter Tech Pants look sharp at the office, but they're chilled enough for beers with the boys. Plus, they won't crush your balls.
Pro tip: Grab two or three pairs in different colors for versatility.
Button-downs: A great way to prove you're a grown-up. Go for neutral colors or simple patterns, with a tailored fit and a collar that holds its shape.
Sensible outerwear: Pick up a couple of jackets to suit different occasions and weather conditions. Try a lightweight bomber or technical jacket, a neutral-toned blazer, and a water-resistant layer.
Shoes that aren't falling apart: You really only need three pairs of shoes to look good: everyday sneakers (not your gym shoes), business casual leather shoes, and smart casual boots.
Pro tip: If budget is an issue, invest in quality over quantity.
Simple, high-quality accessories: A leather wallet, an analog watch, and a leather belt are all you need. Add classic sunglasses for the summer.

How to overcome budget issues

We know you're not made of money. So, treat this section more like an end goal rather than a weekend shopping spree.

If you have to choose between items right now, make sure to invest in quality.

The great thing about being 30-plus is that your fashion lifecycle is much longer — buy well now and you shouldn't have to make major changes to your wardrobe for years.

Focus on fit, colors, and fabrics

As you compile your style arsenal, there are three key areas to focus on:

Fit is king: Clothes that match your physique look so much better than baggy fits and button-popping muscle shirts. A $50 shirt can pass for a $500 shirt with proper tailoring.
Think in color palettes: Building a wardrobe of sophisticated neutral hues gives you lots of options to play with. It also provides the perfect backdrop for a strategic pop of color.
Fabric matters: Fabrics can make a big difference to the vibe of your outfit. If you want to look sharp, try upgrading from cotton blends to merino wool, subtle textured fabrics, and performance materials.

Step 3: Balance maturity with style

When you're 20, you can dress however you want. No one expects you to have taste.

The story changes once you pass 30. Now you're expected to show some signs that you're maturing as a man.

But that doesn't mean going straight to grandpa mode. The key is to sprinkle some maturity into your personal style.

Here are some examples.

Saturday afternoon hangout

Back in the day, you'd roll out of bed, throw on some cargo shorts (*shudder*) and an oversized tee, and slip on your only pair of sneakers.

But the 30-something you has more class:

Jetsetter Tech Pants in Olive Green or Deep Blue (slim fit).
White or light blue henley, or a crisp T-shirt.
Clean, minimal sneakers (think Common Projects or stylish leather trainers).
Optional lightweight bomber or casual jacket.
Fitted baseball cap or smart casual watch.

Relaxed, not sloppy. There is a difference, fellas.

Work happy hour or networking event

Remember when dressing to impress meant wearing a wrinkled button-down with chinos? You're way past that — you need something like this:

Jetsetter Tech Pants in Charcoal Gray or Deep Blue.
Tailored button-down (tucked in).
Blazer that can be dressed up or down.
Leather dress shoes or leather boots.
Minimal, classic watch.

This look suggests a put-together professional who can still appreciate a complimentary bar.

Wedding or formal celebration

As a man in your thirties, there's really no excuse for turning up in a baggy rental tux.

Here's the formula:

Well-fitted suit in navy or charcoal.
Crisp white shirt.
Neatly tied tie.
Leather Oxford shoes.
Tailored fit that shows you understand proportion.
Groomed hair with intentional style.

There's nothing overly fancy here. It's just about avoiding the "remembered I needed a suit last night" look.

A brunch date

This is the real tester. You want to appear mature and put together, without looking old.

Try this for your next date:

Jetsetter Tech Pants in Oak Khaki or Sand Stone.
Our new Tech Polo, or a casual button-down like an Oxford (try rolling the sleeves casually).
Clean loafers or sharp, minimalist leather sneakers (absolutely no gym shoes).
A decent watch.
Sunglasses that actually suit your face shape.

Just running errands

You know those busy weekend days where you're just handling chores, but you might run into someone?

Best to put in a little effort:

Jeans are just fine.
A high-quality Tech Shirt or a simple, nicely fitted crew-neck sweater.
Clean sneakers that aren't your designated lawn-mowing pair, or stylish slip-ons.
A presentable zip-up hoodie or a light field jacket if needed.
Maybe a simple cap (worn forwards, we beg).

See, nothing special. It just guarantees that you don't look like a complete slob.

Step 4: Add some flair

Let's take stock.

You have all the staples in place. And you've figured out how to dress like you own a mirror.

Good work, soldier. Now it's time to turn your style up to 11.

The best way to reach that prime number is by adding little hints of flair. We're talking about…

Accent pieces that pop: You're allowed one statement piece per outfit — a unique watch, an interesting jacket lining, bold socks, or distinctive sunglasses. It's the contrast between neutral and dazzling that really elevates your look.
Mixing different fabrics: This is another way to create visual interest. It could be a wool blazer with a silk pocket square, textured chinos and a smooth button-down, or a knitted sweater paired with a crisp collar.
Embracing subtle patterns: Ones that whisper, rather than scream. Micro-checks, subtle herringbone, and understated plaids are all solid flair plays.

When in doubt, we always recommend staying at the subtle end. People will still notice your touch of flair, they just won't need sunglasses to protect their retinas.

Step 5: Up your grooming game

Dressing well in your thirties isn't just about the clothes you wear. People remember the complete package.

There's little point in putting on a designer suit if you don't own a comb. And no amount of smart-casual style is going to make up for any overpowering BO.

In other words, don't forget grooming.

Here's a quick checklist:

Look after your skin: You might have survived this far without touching moisturizer, but it's time to do something about that bone-dry forehead. Cleanse, moisturize, and protect with sunscreen.
Do something with your hair: If you really want to secure a place as your street's style icon, it's worth getting a better trim. Find a stylist, not a barber. And look after your hair.
Manage your facial hair: You are not Jason Momoa. You're definitely not James Harden. Taking a few minutes to trim up the edges of your beard is way better than being mistaken for a drifter.
Try a little scent: Having impressed with your outfit, you can seal the deal with a great cologne. Choose one and stick with it — this is your aromatic signature. Just don't smother yourself… people need clean oxygen in your presence.

Step 6: Own your look

You're now suited and booted, groomed, and smelling good. Time to head out.

Wait. Don't forget the most important ingredient: confidence.

When you try something new with your personal style, it's easy to feel a little nervous — even at your age.

But just look in the mirror. That's a pretty stylish man staring back, right? (Albeit with a slight expression of fear in his eyes.)

The truth is, nothing bad is going to happen if you don't nail your color combinations the first time. A little too much patterning isn't going to cause a local riot.

And just as importantly, you can carry off anything with a little chutzpah.

Look at A-listers on the red carpet — they somehow look kinda cool even when they're wearing ridiculous outfits.

So whatever you choose to wear, own it.

Turn your 30s into your most stylish decade

Well look at you now. In the space of 10 minutes, you've turned curiosity into pure fashion knowledge. You're primed to turn heads and transform your wardrobe for the better.

While you're thinking about style upgrades, be sure to check out our store. We have everything you need for your next outfit — from long-sleeved technical tees to ever-so-comfortable boxer briefs!

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