Layering Outerwear Is Easier Than You Think — Take It From These Experts

The days of wearing slinky tanks atop flowy maxi skirts and sweet summer dresses are over for the year. The increasingly chilly weather calls for a wardrobe adjustment, one that involves warmer pieces and, of course, knowing how to pile more than a few on. That’s where learning how to layer outerwear comes in: It maximizes warmth while packing a huge punch of personality. So stop reaching for the same black puffer jacket and start capitalizing on the colder temperatures as a way to express yourself.

Wearing your coat with a heavy sweater or jacket (or even another coat!) needn’t be daunting — even if it doesn’t come easy at first. “As a sun-reared transplant from Texas, the art of layering did not come naturally to me,” says Joe Van O, stylist and creative director at Elena Velez. “But once you can integrate the adventure of the climate into the story of your style, the whole process starts to feel very rewarding and luxurious.”

The key is starting with a base layer that’s both functional and versatile. “I suggest investing in quality underpinnings (T-shirts, tank tops, and leggings) so you can feel beautiful in every step of getting dressed,” Van O tells TZR. “The trick is actually to build a series of several light layers that can be shed one at a time to best serve the needs of your day.” By starting with a simple foundation, a variety of outerwear basics will cleanly fit on top without distracting the eye or adding too much bulk.

“You can always rely on the standard of layering lighter to heavier to get a more streamlined look,” says Ty Hunter, longtime stylist of Beyoncé and Destiny’s Child. His go-to layering piece? “Definitely my long black cardigan. I can wear it with anything. I can layer it or just wear it as my jacket,” he notes.

When building a multi-dimensional outfit, Van O advises to think of playing with color and texture. “You have to find the common thread of the look and keep it going in every last detail,” he explains. And don’t be afraid to pull other seasonal pieces into your winter wardrobe. “A spring jacket under a cropped jacket can give you a more modern look,” Hunter tells TZR.

From trench coats to vests, leather jackets to casual puffers, there’s just so much to play with in cooler weather — especially when paired with the right accessories. Adding thick scarves, tall boots, and cozy hats will take your layered look to the next level. “When building any successful outfit, I suggest starting with one piece in your closet that inspires you in what you want to say about yourself that day,” Van O explains. “From there, every other component of your outfit should speak in harmony to that one [central] piece.” Start by investing in a statement coat or funky vest and build upon that single staple.

Keep reading for a few layered outerwear looks worth trying this season — and tips on how to achieve them with complete comfort and flair.

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Sweatshirt + Leather Jacket

It’s the ultimate cool-girl combo: a comfy, oversized sweatshirt with an edgy leather jacket thrown loosely on top, the perfect balance of effortless and put-together. Van O agrees: “Layering is all about strategy, and I love pairing high and low as a general rule of style,” he says. Not only will the combination of fleece and leather keep you warm for a day of coffee runs and errands, the pairing is extremely versatile, taking you seamlessly from day to night. Try pairing with matching bottoms: sweats for a more casual look, or black leather pants for a sophisticated approach to comfort. Round out the ‘fit with some platform boots and cat-eye sunglasses for the quintessential model-off-duty look.

Jumpsuit + Puffer

The resurgence of crisp autumn air signifies the return of perhaps the most timeless outerwear staple: the puffer. Update this streetwear-style jacket by tossing it over a jumpsuit for a chic but relaxed style. Try playing with oversized, cropped, and vest-style puffers while experimenting with denim and silky jumpsuits to find a vibe that works for you.

Zip-Up, Blazer, + Cropped Jacket

Nothing levels up an outfit quite like layering, and Forbes style contributor Olivia Perez (above) has mastered the art of piling on clothes. Follow her lead and try throwing on a zip-up hoodie, blazer, and, as a finishing touch, a cropped jacket. This look can be achieved with a variety of textures and colorways, making it a reliable combination that withstands any trend cycle. Such a layered outfit runs the risk of looking busy, too, so be sure to stick to a general theme. “A common misconception people have when putting together an outfit is that having color or prints in your outfit reflects more personality or self expression,” Van O reflects. “However, when you look at the most successfully explosive outfits, they usually follow the rules of tonal balance that honor the extremity of the pieces.”

Collared Knit + Overcoat

Outerwear doesn’t always have to be casual. Elevate your cold-weather style with a classic long overcoat and sophisticated collared knit. Preppy-meets-practical with this foolproof combination, especially when you pair it with a mini skirt, tights, and knee-high boots. Stick to a warm colorway (but don’t be afraid of throwing in a few patterns), adding coziness to the gray winter days. Complete the look with a classic shoulder bag and cat-eye sunnies for the ultimate Parisian-style outfit. As Van O says, “Your coat, shoes and bag should always be the biggest investment in your personal wardrobe and will be the key to achieving a strong sense of personal style on a daily basis.”

Jacket + Sweater

Keep it simple this season with basics you’re likely to find in your closet already. A chunky sweater pairs beautifully with an oversized zip-up jacket, perfect for the crispy days and colder nights. Tie the knit loosely around your shoulders for when the sun peeks through, or layer the look with a scarf and straight-leg jeans when the temperatures drop. The simplicity of this outfit also leaves room for it to be reinterpreted through a variety of accessorizing choices. “I believe in dressing the way you feel,” Hunter says. “If you feel good in it, you can't go wrong.”