• <h1>10 Ways To Wear Sweatpants This Fall</h1>
  • <h1>10 Ways To Wear Sweatpants This Fall</h1>
  • <h1>10 Ways To Wear Sweatpants This Fall</h1>

10 Ways To Wear Sweatpants This Fall

The modern guy’s guide to pulling off this casual staple

There are few articles of men’s clothing as divisive as sweatpants. At their best, they’re just as contemporary and current as your best pair of chinos. At their worst, they’re the epitome of slacker style. All too often, as you venture through the nation’s airports, you pass by legions of fashion offenders. There are men everywhere who seem to think traveling is an excuse to eschew all style in favor of comfort. Baggy sweatpants, with matching hoodies, rear their ugly heads (or shall we say bottoms) time after time.

But it isn’t just Gate B26 where sweatpants keep popping up. You see the bad ones everywhere. On dads making pit stops at the gas station for a fill up and a snack. On the rustic guys making a quick run to Home Depot for last-minute supplies. On the college athletes who seem to live in their warm-up gear all semester long.

It’s not to say that sweatpants aren’t allowed. Because they absolutely are. But the dated application with wide legs and baggy fits are so bad they’re offensive. If we’ve learned anything about streetwear and men’s fashion in the last few years, it’s that everything looks better in a slimmer cut. That includes sweatpants.

The newest incarnation is beautifully tailored. They evoke the craftsmanship of your favorite dress pants but still pack in the effortless cool of your casual looks. Modern sweatpants, dare we say it, can look smart and stylish. They successfully toe the line between trendy and classic. They’re singlehandedly reinventing off-duty style.

Some Brief History

Before they were reinvented, sweatpants had a slightly different trajectory. Back in the 1920s, Le Coq Sportif founder Émile Camuset created the first pair for athletes. The goal was to allow them to stay comfortable while being active and while stretching. They were made of jersey and came in the signature gray hue that’s now synonymous with sweatpants.

Over time, athletes have continued to latch on to the casual style. Especially in fall, the traditional casual pants are ideal for warming up outdoors. They’re loose and thick. For a guy who spends a lot of time on the football field or the track during the colder months, the baggy application makes sense.

But athletes aren’t the only ones who’ve realized the benefits of comfort. Men everywhere have a pair of these pants in their closet. At one point, they became the comfy pant of choice for chores and yard work. But then, they became the early morning substitute for style; the pant of choice when pulling together a basic look was just too much.

Only in the last six years did we start to see a revolution of sorts in the sweatpants realm. High-end designers like Thom Browne started sending sweats down the runway. Soon after, every major retailer was stocking shelves and racks with the new slimmer cousin of your dad’s favorite pair. That brings us to modern day.

Things To Consider When Buying

Not to pass judgment on retailers like Wal-Mart or Target, but if you’re looking for a finely tailored pair of sweats, you won’t find them in places like these. You need a trusted brand that understands the nuances of what makes a great pair of sweatpants. The lower on the totem pole you go, the more quality and fit you have to sacrifice. We offer a wide variety of sweatpants in different designs, colors, and fabrications-all of which are tailored and crafted to fit beautifully.

Don’t Wear Them Everywhere
Upgrading your sweatpants is an exciting experience. You’ll probably want to wear them everywhere but resist the urge. While it’s true that these new ones are more appropriate for your daily activity than the old baggy variety, they’re still casual. So rock them for casual situations like running errands, heading to the gym, or traveling. Odds are, unless you work in a pretty casual startup setting, these pants won’t work for your 9 to 5.

Rock ‘Em With Style
Remember that you’ve upgraded. This means you also need to upgrade the other pieces you wear with your sweats. Abandon the flip flops and slippers. Dump the ratty t-shirt. Treat them the same way you would a pair of chinos or denim. You’ve invested the time and the cash. Know that your new sweats deserve better.

Not Too Tight
Tailored is one thing. Tight is another. Make sure that you still have a full range of movement when you’re walking. Also make sure you’re not showing off any underwear lines or exposing anything else that should stay hidden.

You Need A Slouchy Crotch
Speaking of showing off things that should still be hidden, make sure the crotch on your sweats is slouchy. Not necessarily a drop crotch, but loose enough to keep things casual and avoid any embarrassing situations. Your sweats shouldn’t fit like a pair of running tights.

Distressing Is A No-No
One of the biggest trends in denim right now is overdone styling: frays, stains, rips, patchwork, etc. The same can’t be said for sweatpants. If yours are distressed or overly treated, they’ll just look sloppy. And the entire point of tailored sweats is to look cleaner and neater.

Boxers or Briefs? Both
As is the case with any slim pants, you need to wear underwear that isn’t restrictive. You also need a pair that won’t bunch or ride up as you’re moving throughout your day. Boxer briefs tend to be the best option.

Perfect the Stack
The stack is the styling option where you see guys with their sweats hiked up above their ankles and just below their calves. Most tailored sweats made from a thicker cotton and with a tapered leg opening lend themselves to a great stack. Just pull them up a little and you’re ready to go.


The great thing about the new breed of sweatpants is that they integrate extremely well into various looks. Though they might be relegated to casual situations, it doesn’t mean your styling options are limited. In fact, the possibilities are endless. But to save you some time, we’ve whittled down the options to 10 looks that will suit you for different types of weather and aesthetics.

Longline T-shirts
Your new sweatpants are slim and tailored. One of the best ways to show them off is by playing up proportion. Where your bottoms are restricted and pared down, a longline t-shirt is free. The length, with a hemline that hits just under your bum, offers a stark contrast. For example, the Stripe Hem Longline T-shirt with Side Zipper works well with our Ribbed Jogger Sweatpants. For an extra style move, pull a sweater over your longline. The look becomes so dapper people won’t even realize you’re wearing sweats.

Denim Jackets
If you really want to treat your sweats like any other pair of pants in your closet, pair them up with some of your best outerwear. A denim jacket, like our Button Down Trucker Denim Jacket, keeps you in casual territory but adds versatility. Under the jacket, you can work in a cotton t-shirt. Or if you’re meeting a friend for coffee, try a polo or casual woven shirt instead.

Bomber Jackets
Bomber jackets really play up the athletic feel of the sweats. It doesn’t take much to make this look pop. Gray sweats with our Basic Woven Zip Up Bomber Jacket create a simplistic yet hyper stylish look. It’s casual cool that works for an afternoon at the hardware store or to take in the big game at your local watering hole. Stick to layering in a t-shirt underneath the bomber.

With a topcoat, some guys might actually be able to pull these off at the office. There’s something about a topcoat that makes everything look more elevated and refined. The three-quarter length is indicative of more formal events. And in a beige or cognac color, the coat adds a sense of polish to even the most casual slacks. Toss on a topcoat with your sweatpants. With a sweater and woven shirt above the waist, you’ll be ready to close big deals in the boardroom while still rocking your sweats.

Tank Tops
For the warmer fall days, you’ll want less layers. But you have to be careful about what shirt you choose. If you go too plain, you’ll look far too casual. A boring top above the waist reduces the stylish quality of your tailored sweats. For best effect, choose a tank top with a bold new design. Since you’re likely solid down below, the print helps balance everything out. For an athletic look, try our Brooklyn Chicago NY Basketball Tank Top. Or for a more versatile casual look, go with the Faded Americana Tank Top.

Throughout this sweatpants tutorial, one of the key themes has been treating your sweatpants like any other pair of pants in your closet. Another way you can do this is to create smart looks. Instead of a jacket, tank, or tee, opt for a sweatshirt with some subtle modern detail. Our Basic Quilted Faux Leather Sweatshirt has the look of dress sweater with the feel of a well-crafted worn-in piece. Pair it back to your sweats, but add some details to make the look chic. Gently roll your sweatpants to create a small cuff and rock them sockless with a pair of casual oxfords. When you see this look completed, you’ll even forget that you’re in sweats.

When you rock a cardigan with your sweats, you create a modern collegiate look. Cardigans are fall essentials that communicate a studious, mature quality on their own. With a pair of sweats, they become a bit more relaxed while simultaneously elevating the entire look. Rock them with a pair of simple sneakers and a messenger bag. You’ll be the best dressed man on campus by far.

Sometimes, rocking sweatpants isn’t about trying to take them up a notch. And that’s okay. There will be times where you’ll just want to be comfortable. The good news is that you can do this while still looking great. With an equally tailored hoodie, you can pull off a simplistic athletic look that keeps you on trend. Our Basic Long Sleeve Pullover Hoodie Shirt and Marled Fleece Full Zip Hoodie Jacket are great examples of expertly tailored pieces that pair well with sweatpants.

Casual Shirts
Don’t feel limited to the most casual shirts on the market. You have other options. Casual shirts with prints and patterns can work just as well. These shirts help you build on a few of the skills learned from the previous looks. Casual woven shirts help you play with proportion, color, and details. Keep them untucked and stack the bottom of your sweats a bit. Choose a more casual shoe. Instead of a trainer, try a low-top sneaker. Our Woven Chambray Button Down Shirt is a great long-sleeve option while the Roses Zip Short Sleeve Shirt is a more adventurous alternative.

In step with the desired casual effect of hoodies, t-shirts can help you pull off the same thing. Just be conscious of fit and design. As mentioned, longlines work well with joggers. This is because, despite their length, they’re still tailored. They’re long but not oversized. With regular t-shirts, it’s important to pick up something that’s cut slim so your overall silhouette stays slim. But also choose a bold design that helps break up the monochromatic feel of your sweats. The Urbancrews United Printed Crewneck T-shirt and the Brooklyn Red Roses Crewneck T-shirt are fantastic options.

Sweatpants started out as a functional pant for athletes. And over time, they’ve maintained their place in the sports world. But now, in the hands of fashion and streetwear enthusiasts, there’s a brave new world of tailored sweats that are more versatile and stylish than anything your dad ever wore. Treat them like your favorite chinos or denim and unlock the possibilities. If there’s anything important to remember, there really are no limits when it comes to the new breed of sweatpants.

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