How to Style a Sweatshirt for Fall: 6 Polished Outfits

A sweatshirt looks put together when the pieces around it are sharper than it is. Pair a relaxed crewneck with something structured, a pointed boot, a collar, a pressed hem, and the whole outfit reads intentional instead of off-duty. Below are six ways to wear one this fall, from weekday errands to a Saturday dinner.

How do you make a sweatshirt look put together?

Balance the softness of the sweatshirt with one tailored or polished element. That can be a structured shoe, a crisp collar showing at the neckline, or a bottom with a clean line, like straight-leg denim or a midi skirt. Keep the sweatshirt itself in good shape: no pilling, no stretched cuffs.

Fit matters more than brand. A sweatshirt that hits at the hip, or one you can tuck at the front, gives your outfit a waist and keeps it from looking borrowed.

What to wear with a sweatshirt: jeans and boots

The most reliable sweatshirt outfit is straight or wide-leg jeans with an ankle boot. A front tuck and a boot with a pointed toe do most of the work.

Start with a striped crewneck like the Stripes and Spice Pullover, where the sage stripes and rust trim already do the color work for you. Add dark denim and a western bootie such as the Avery Beige Western Booties; the woven detail gives the casual top something refined to sit against. For more ways to wear a bootie this season, see How to Style Ankle Booties for Fall.

Can you wear a sweatshirt with a skirt?

Yes. A sweatshirt over a midi skirt is one of the easiest ways to dress one up. Satin, pleated, or knit skirts all work; the contrast between a soft top and a skirt with movement is the point.

Tuck the front of the sweatshirt or let it sit just at the waistband. Finish with loafers, ballet flats, or a slim knee boot. A printed sweatshirt, like the Rose Garden Floral Sweatshirt with its mauve florals and striped sleeves, pairs well with a solid skirt in cream, brown, or black.

How do you layer a collared shirt under a sweatshirt?

Wear a button-down or a thin collared top underneath and let the collar and an inch of cuff show. It instantly makes the outfit look considered, and it works just as well for the office as for the weekend.

Choose a shirt slimmer than the sweatshirt so it doesn't bunch at the arms. A white or striped shirt keeps it classic; a plaid collar under a solid crewneck adds a little more fall to it. Our guide to layering clothes for fall covers how to keep layers from feeling bulky.

How do you style an oversized sweatshirt?

Keep one half of the outfit fitted. If the sweatshirt is roomy, pair it with leggings, slim jeans, or a short skirt with tights so your shape still shows somewhere.

An oversized crewneck over a long-sleeve mini dress also works well on cooler days: the hem peeks out below, and tights with a low boot pull it together.

What pants go with a sweatshirt besides jeans?

Cargo pants, wide-leg trousers, and joggers in a nice fabric all pair well with a sweatshirt. Cargos lean relaxed and a little street-style; tailored trousers lean polished.

For weekends, try a fitted sweatshirt with the Blending In Camo Cargo Pants. The olive camo and wide leg are casual on their own, so keep the top simple and add a clean white sneaker or a slim boot. For something more grown-up, swap in a pleated trouser and a loafer.

Can you wear a sweatshirt with a jacket?

Yes, as long as the jacket is longer or roomier than the sweatshirt. A shacket, a wool coat, or a denim jacket sized up all layer cleanly over a crewneck.

A sherpa-lined shacket is the coziest option for cold mornings and football games. A long camel or charcoal coat over a sweatshirt and jeans is the most polished version, and it's the one we reach for most once temperatures drop.

The finishing details

Small choices make the biggest difference with casual pieces. Push the sleeves to the forearm, add gold hoops or a simple chain, and pull your hair up so the neckline shows. A sleek claw clip twist is a good match; see How to Wear a Claw Clip for six easy styles.

Orders over $75 ship free, so a sweatshirt and a bottom to wear with it is an easy place to start.

FAQ

Should you tuck in a sweatshirt? A front tuck works best for most sweatshirts. It defines your waist and keeps a relaxed fit from overwhelming the outfit, especially with high-rise jeans or a skirt.

What shoes go with a sweatshirt? Ankle booties, loafers, ballet flats, and clean white sneakers all work. Pointed or structured shoes make a sweatshirt look more polished; sneakers keep it casual.

Can you wear a sweatshirt to work? In a casual office, yes. Layer a collared shirt underneath and pair it with trousers or a midi skirt and loafers so it reads as deliberate.

Are oversized sweatshirts still in style? Yes, relaxed and oversized sweatshirts are still widely worn this fall. Balance the volume with a fitted bottom, like leggings, slim jeans, or a mini skirt with tights.

What size sweatshirt should I buy for an oversized look? Try your usual size first if the style is already cut relaxed. Size up one only if the sweatshirt is a standard fit and you want extra room through the body and sleeves.