How To Dress in Your 30s: Far From Old, No Longer a Child

You likely have a bit more money. You’re also still young enough to have fun with fashion but too grown-up to do it indiscriminately. Let’s navigate how to dress for your 30s.

No offense to my 20-something brothers, but your brain isn’t fully formed. Early developers might have an intact prefrontal cortex, the place that helps you make good decisions, by 25.

So, I don’t judge 20-somethings who date the wrong girls. Nor do I judge the guys who order the wrong drinks (martinis are made with gin, not vodka), and, yes, wear the wrong clothes. Past that, though, one should know how to dress in one’s 30s.

By the way, I’m half joking. There’s no truly wrong way to dress at any age. Do what you love and be yourself.

Your 30s, however, can present an interesting sartorial balance. You might finally be making good money and shopping on your own for quality clothes without the help of mom and dad.

You’re also still young, and you’ll be young for quite some time, so you don’t want to go full grandpa (or maybe you do. No judgment). All that to say, you want to look like you have your act together. Don’t worry. These constraints are, ironically, quite freeing for any personal style.

How To Dress in Your 30s: Where To Start?

When it comes to dressing in your 30s, an easy place to start is your job. What do you have to wear to work? From there, you can think about how to optimize the look.

Even more, you can strategically omit, add, and swap pieces to get your weekend or casual Friday look.

Optimize Your Suiting: Getting the Right Fit Isn’t As Strict as You Think

If you wear a suit to work, the most important thing is fit. Now that you’re a grown-up, it really is best not to participate in trendy cuts heavily.

“Cool” suits were skinny in the aughts, cropped in the late 2010s, and oversized in the mid-2020s. Now, if you work in the fashion industry or trendy industries in general, you might feel obligated to participate in these trends. Or rather, you might feel the need to be ahead of them.

That’s a different conversation than the one we’re having here, which is aimed at the more “everyday guy”, if you will. By the way, guys can dip into trends here and there every day, and I’ll get to that momentarily.

There’s more room for self-expression in classic tailoring than you think. Many consider Cary Grant a classic style icon when it comes to tailoring, and so is George Clooney. They wear completely different cuts of suits. Every single James Bond also wore a different fit of suit.

Does this mean that classic tailoring doesn’t actually exist? No. It does exist. It just ranges.

I’ve used modern royals as an example of timeless style on several occasions. Why? Because few are bound to sartorial rules to the extent they are. King Charles III wears a looser-fit suit, while William, the Prince of Wales, wears a slimmer one.

Ironically, Gen Z’s obsession with oversized fashion means the baby boomer King’s tailoring is more akin to their style.

The point is to find a cut that isn’t baggy or skinny that you’re comfortable in and that complements your body type.

Choose Classic Fits

Here’s the true secret to timeless tailoring — the quality that unifies all cuts and fits we call classic.

No matter which classic fit you choose, the jacket shoulders should sit perfectly. Consult a tailor about this, but this usually means just a quarter of an inch out from your shoulder bones. The top of the sleeves should hit the seams without a divot and without tension.

In fact, once you have that down, you can occasionally dip your foot into trendy suiting here and there. Again, being in your 30s means you’re still young enough to do such things. Just save it for the weekends, casual Fridays, and nights out at bars or restaurants, and not the boardroom.

Optimize Your Suiting: Accessorize To Make It Yours

I’ve long advocated for the dark olive suit and the maroon suit. They’re fun yet grown-up, which is the balance you want to strike when it comes to dressing in your 30s.

You can also go for a true blue suit instead of a navy one. I wear a suit to work every single day, and I only own three. I have a navy, a gray glen check with subtle blue accents, and a true blue suit.

If a pocket square doesn’t feel too dandy to you, try it out. It adds a touch of old-world class. Just remember not to match it to your tie. They should complement each other.

If you want to level up the formality, you can go for a full three-piece suit, vest and all. Layers add structure and a sense of distinguished character.

I never like to look overly formal myself. So, I often add a touch of coziness via a cable-knit sweater vest or cashmere pullover under my suit jacket. I also tend to go for loafers over lace-ups.

Dressing in Your 30s: Smart Casual and Business Casual

Being in your 30s gives you room to still participate in niche fashions. A good example is wearing a suit with a T-shirt, which we’ve fully explored here.

I’m also a fan of the broken suit, which is more classic. My go-to weekend look is khakis, a cricket sweater with a button-down, and a navy blazer. I’ll opt for white leather sneakers or loafers, depending on my mood.

If your place of work has a business casual dress code, which most do these days, check out our guide on it. It’s a wide-ranging dress code, and as such, it’s tough to navigate. What’s acceptably casual in one office environment may not be in another.

My biggest piece of advice is, as a grown-up, it’s now time to avoid extreme high-low combinations. Sure, a polo with slacks or sneakers with a suit is age-appropriate in the right context.

I’m talking baggy scoop-neck t-shirts with a suit jacket or ripped blue jeans with a dress shirt and tie. Graphic tees, which you can style appropriately in casual situations, are too irreverent in smart casual and business casual dress codes.

In fact, leave irreverent and jocular verbiage for the memes. Gone are the days of early aughts t-shirts with funny or “edgy” messaging. It should go without saying that this is especially so in smart casual and business casual settings.

Dressing in Your 30s: Work Casual vs. Weekend Casual

Remember, a casual day at work is different from a casual day spending the weekend with close friends. And this goes for even the most casual offices. Even if you see guys running around your office in baggy, stained t-shirts and cargo shorts, I’d avoid it. “Do better,” as they say.

The best way to look “together” in a relaxed setting is to emulate a formal silhouette using casual clothes. A button-down with a pair of jeans and sneakers has the same overall shape as a dress shirt and trousers.

A leather jacket, sports jacket, Harrington, or even a safari jacket adds the kind of structure your suit jacket would give you. In fact, layers are a great way to level up a casual outfit while making it more you.

Choose a bomber jacket to add a cool factor or a cardigan for a more elegant look.

While this may start to dip into the smart casual category, you can always level up your relaxed combination. Do this by incorporating one dressy piece. Leather oxfords, or any dress shoes, with chinos work well. So do tweed trousers with a t-shirt and a dress shirt with jeans.

Does your job require you to wear workwear style? Well, you can actually incorporate that very aesthetic into your day-to-day outfits, too.

Don’t run around in steel-toe boots and a hard hat, but a lot of workwear-inspired garments are menswear classics. Where do you think jeans come from?

Fitted cargo pants and a utility shirt, waxed jackets, and leather service boots are all stylish options

Finally, remember how shorts should fit properly. Make sure that the hems don’t go past the knee.

How To Wear a T-Shirt and Jeans

Again, the fit is all-important: Not too skinny, not too baggy, and cuts that flatter your body type.

Beyond that, you can always add dynamism to your t-shirt and jeans with layers. Or level it up with your shoes or accessories. When you wear a simple T-shirt and jeans, your watch might become the outfit’s statement piece.

Graphic tees aren’t completely inappropriate. Vintage graphic pieces, for example, have a rocker vibe to them, which might be your style. Others might have a retro-cool aesthetic that would pair well with Nike Killshots.

My advice here is to add a layer, maybe to temper the graphic. For example, an open utility shirt or one that’s buttoned halfway up, exposing a bit of the imagery.

Things To (Mostly) Avoid

The 30s is a liberating time when it comes to clothes. You aren’t too old or too young. However, here are some garments and approaches to either avoid or approach with caution:

Extra skinny fits
Overly baggy fits
Wearing your pants low
Too many graphic T-shirts
Unbuttoning your shirt past the third button-down
Technical trainers meant for the gym
Jeans with several or gaping rips
Jeans that are overly distressed
Dirty sneakers
Neons
Underwear tank tops worn as shirts
Open-weave mesh
Inappropriate graphics (if you can’t wear your graphic tee around your grandmother, then don’t wear it at all)