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How to Dress Casual without Looking Like a Teen

Dressing well is a skill-set that requires serious honing. But, rarely do we consider style in the same context of woodwork, basketball, or cooking. We wear clothes because we have to—grab a shirt, pants, underwear, and we’re good to go.

But, if style were an inherent trait for all of us, we’d be looking our best at any given moment.

There are certain things you already know. For instance, putting on a tailored suit and tie makes you look like the worldly, sophisticated man you are on the inside. But, the trouble lies in the nuances of casual dress, where comfort trumps style. But looking good and feeling comfy don’t need to be mutually exclusive.

With that in mind, we think it’s time for a style intervention. Here are some easy tips for getting out of your teenage hoodie phase once and for all:

Why Does It Matter?

Impressions. Even if you work at home, chances are, you’re going through life and talking to people in the process. Dressing for success can actually lead to success—and it makes sense. There’s no denying the benefit cool, well-fitting clothes can have on our self-esteem and the way others see us.

When we pair an old sweater with a super hero tee, it implies that we’re stuck in an arrested development. A simple swap—plain, fitted tee and a nice sweater—is just as comfortable, but a lot more grown up.

What’s Appropriate for the Casual Office Space?

It used to be that, as an office-bound man, you’d alternate between your gray and navy suits—easy, predictable, and best of all—unambiguous. Nowadays, there are the notoriously tee-shirt-clad tech bros, co-workers who wear flip-flops, and more.

So, when there are no rules, what are the rules?

Jeans: keep these dark and free from rips (yes, even the store-bought kind). Fitted jeans are great but go for a straight cut instead of a skinny pair. You’ll thank us for this advice if you’re being squeezed all day in the

Pants: Cords, chinos, even light wash denim. Slim trousers. You name it. Again—it’s all in the fit. Light denim is tricky—but it can be office appropriate if worn with a crisp white oxford.

And since we’re talking bottoms, ditch the tired running shoe and jean combination. Loafers, Chelsea boots, or a gleaming white pair of Stan Smiths should take the place of the gym shoe. If you want more info about shoes, check out our guide to men’s shoes here.

When Can I Wear Athleisure?

Oh boy. Men's casual is in an exciting place these days. Yes, designer sweat suits rule the streets and the runways, but they're a little tricky to pull off with aplomb.

On the one hand, it could be seen as a positive that our most comfortable fashion inventions have made their way into our day-to-day. But, steer clear at the office or keep the sportswear to a minimum.

While women face the yoga pants/leggings debate, men have a similar issue with sweats—they skew inappropriate and look kind of pajama-y.

If you like the sports-inspired look, pick one piece at a time. Think fancy sneakers with navy, cuffed chinos, sleek, fitted joggers with a shawl cardigan, khakis or black pants with a track jacket.

Head-to-toe sportswear, on the other hand, is best left to the true gym rats.

Skip the Graphic Shirts

Solid shirts are the obvious choice. For starters, just get a pack of black, white, and grey Hanes shirts to wear with your sweaters and favorite pair of chinos or dark wash jeans. It’s easy, requires almost no effort and flatters just about any body type.

If you can’t part with the graphics, it’s time to figure out how to make them look a little cooler and more mature.

Make like Nick Jonas and try a soccer jersey (note that he's not wearing bright yellow or orange), and pair with black jeans—it’s not "plain," but has the same flattering effect of an all neutral outfit.

For the office, you may want to look for polo shirts, oxford cloth button-ups, and long-sleeved Henley-type shirts.

Up Your Topper Game

The shawl cardigan is a good alternative to those zip-up hoodies from American Apparel we’ve all worn for the past decade. It comes with the same coziness factor—heavy weight, easy to throw on over a solid tee when the chill hits.

A weekend workhorse and office staple, the shawl collar is the ultimate investment piece. We’d advise shelling out for a good one—Banana Republic and Bonobos offer some good options in the higher to mid-range.

If you’re on a budget, don’t fret—sometimes fast fashion has a good buy here and there—think H&M, ASOS, or J. Crew Factory.

But, don’t stop there. Shawl cardigans are great for staying toasty when it’s nasty outside, but sometimes lighter fare is in order. Look for basics like this cotton Club Monaco cardigan—versatile grey, with that hint of piping to add some interest. Or, this double-lined Brooks Brothers camel number.

Pull-Overs, too are a good option. Toss your worn out crewneck and look for a slim-cut pull-over sweater. They’re available at all price points. Uniqlo makes some good ones in the $30-40 range—making it easy to stock up on a few colors to change things up. Or go more rugged with this LL Bean pick.

Need an extra layer? Invest in a denim jacket and bam—you’ve got more than a few layering options for your tees and button ups. Easy. As. Pie.

You can’t go wrong with a classic Levi’s Trucker jacket. You’ll get more mileage out of the darker washes, so stick with black or dark denim. Or try this fleece-lined Native Youth jacket—the grey color and the lining add a dash of style to an old favorite, without getting too “trendy.”

Consider This a Wakeup Call

Sometimes we need a wakeup call to get out of a rut—sartorial or otherwise. You might not think looks matter, but unfortunately, they do. With more and more workplaces adopting flexible schedules and casual dress, band tees and wearing the same pants every day just aren’t going to cut it anymore.

It’s also worth pointing out that, investing in better tee-shirts and a couple of sweaters and jackets gives you a big dose of style—with minimal effort. Consider this the adult version of your high school sweatshirt and hole-y jeans look.

Trust us; you’ll thank us when you run into a potential new client at the grocery store or have a meet-cute situation with that gal down the street. The point is, you’re better off dressed for a chance encounter.

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