Winter Outfits That Never Go Out of Style

Are you a sweater lover fighting the urge to dress like a snug snowball instead of keeping your fashionista vibes strong this winter? Your winter outfit style doesn’t have to be one or the other! 

At The Willow Tree Boutique, our ideas for cold-weather fashion make dressing for the day easier than you think! With so many chic winter looks, you can work with what you already have in your wardrobe, create unique outfits, and stay warm while looking fabulous! Check out these winter clothing items to design outfits that never go out of style.

P.S. If these are outside your comfort zone, winter is the perfect time to experiment with your winter outfit styles. Seize your chance to develop some bold looks, and maybe you’ll discover something new to love and keep with your winter essentials.

1.Show-Stopping Coat + Jumpsuit

A woman wearing an animal print coat

Your outerwear deserves special attention as one of your closet's most important winter clothing items. You may have your go-to black or navy trench coat that goes with everything. But it’s time to step up the energy and fight back against gray skies and drizzly weather. 

Make your jacket or coat the show-stopping part of your outfit and wear a stylish jumpsuit underneath to keep those effortless vibes going. We love a sleek, minimalist jumpsuit under a bold coat that ensures your outerwear is the center of attention – the perfect blend of warmth and style!

2.Puff Coat + Leggings + Boots

A woman wearing a puff coat with leather leggings

While puff coats used to be the epitome of sad fashion, the evolution of warming technology has made them sleeker, sexier, and totally essential to your winter outfit style. Get the warmth you want from a puff coat and let it do all the stylish heavy lifting. 

With a simple blouse, leggings, and your warmest boots – you’ll be cozy chic without resorting to a marshmallow puff. At The Willow Tree Boutique, we even have some ultra-unique puff coat styles, like sleeveless duster-length vest silhouettes with hoodies or cropped moto styles with collars.

Since our puff jackets come in many lengths and styles, you might want to vary your bottoms too. If it’s too cold for leggings, our joggers are a great alternative that exude a relaxed, urban style, keeping your look effortless. Joggers do look better with booties or sneakers, though. So, re-evaluate your whole ensemble before heading out the door with this winter outfit style.

3.Teddy Coat + Wide-Leg Trousers

A woman wearing a pink teddy coat with jeans

Like the shacket, teddy coats are a newer fashion trend that look like they’re here to stay. A little sleeker than puffer jackets but way more relaxed than an uptight trench, a teddy coat is the closest thing to wearing a blanket when heading out — kind of like a cross between a cardigan and a coat. 

For this winter outfit style, we definitely say go with volume. Teddy coats are already pretty oversized with their nearly formless silhouette, fuzzy texture, and full-length hem. So play it up with similar winter clothing items that are all about oversized tailoring. 

Pair your coat with some wide-leg trousers or culottes — preferably high-waisted — and a voluminous top that you can tuck into your pants or that already comes cropped. If you feel like you need a little contrast because you’re swimming in this winter outfit style, swap your top out for a bodysuit or something slimmer that accentuates the size of your waist against the wide trouser.

4.Blazer + High-Waisted Bottoms

A woman wearing a blazer with high-waisted jeans

If you’re heading to the office or just feel like giving off professor vibes, consider pairing a blazer with any high-waisted bottoms in your closet for this classic winter outfit style. 

At The Willow Tree Boutique, we’ve got bright gem tone blazers for fashionistas who want to make a statement, pieces with unique details like feathered cuffs or lace cutouts, and simple styles that showcase classic patterns, like houndstooth, argyle, and plaid. Whether you feel black and sleek or prefer a floral, rainbow design to remind everyone of warmer weather, blazers add a professional touch to your look with their tailored, structured design.

Since you’re wearing such a sophisticated piece of outerwear, your bottoms can be a little more relaxed. Keep your winter clothing items corporate with high-waisted trousers, or go casual with body-shaping leggings.

5.Denim + Trench Coat

A woman wearing a trench coat with denim pants

Both denim and trench coats have been around FOREVER! While they were both originally more utilitarian (denim for workwear and trench coats for the military), the fashion world co-opted both materials and silhouettes and brought them over to the style side! We love combining both with a denim bottom of your choice and a trench coat with some unique details.

Whether you like skinnies, flared bottoms, or boyfriend-cut jeans, consider concentrating on your coat to create a unique winter outfit style. Our trench coats have something special to offer with details you won’t find anywhere else, like double-breasted cuts, suede materials, fun patterned buttons, and unusual prints.

6.Cropped Sweater + High-Waist Trousers

A woman wearing a cropped sweater with high-waisted pants

One of our favorite things about high-waisted bottoms is how they accentuate the waist. But if you’re wearing a big puffy jacket, nobody will even be able to see it! Instead of hiding your curves underneath all those layers, we think it’s time to bring back cropped tops in winter outfit styles. 

At The Willow Tree Boutique, you’ll be able to find cropped sweaters, coats, and denim jackets that make nearly any high-waisted outfit come together. Shop neutral winter colors to mix and match cropped tops and high-waist bottoms, or choose just one show-stopper to style your other winter clothing items around.

7.Turtleneck + Mini Skirt + Knee Highs

A woman wearing a turtleneck sweater with a mini skirt

Here’s a look that’s been going strong since the 60s, and it seems like nobody can get enough! This winter outfit style plays with long and short hemlines and keeps it flirty and sassy to the max. Keep warm on top with a body-hugging turtleneck but wear a mini skirt down below. Then, complete the look with knee-high boots to keep you warm in winter weather. 

Our favorite twist on this look? Wearing knee-high socks with clunky Mary Janes or platform sneakers. Of course, you’ll want to top this look with your favorite jacket. Are you going for a cropped denim moto for a throwback 90s vibe or a contemporary full-length duster to complete your ensemble?

8.Moto Jacket + Stirrup Pants + Loafers

A woman wearing a biker jacket

This look has been giving us streetwear vibes since the 90s, and we’re never giving it up. With a moto jacket, you don’t feel swamped in a million puffy layers, while stirrup leggings guarantee your ankles are nice and toasty. Instead of wearing boots or booties, make your look about the loafers, and you’ll be showcasing a blend of urban chic and professor vibes that are simply EVERYTHING!

Loafers are the power behind this winter outfit style, and we have the shoes that truly pop. Browse suede, crushed velvet, and shiny faux leather looks, as well as specialty detailing and colors, like chains, stitching, and platform soles. While we don’t recommend this winter clothing item when it rains or snows, loafers work great for dry winter weather.

9.Show-Stopping Pants + Trench Coat

 A woman wearing floral patterned pants

We’ve already had a show-stopper coat with a sleek winter clothing item underneath, but what about the other way around? If you prefer pants with wilder, bolder energy, this could be the winter outfit style for you. 

Consider bright colors in faux leather, glittering joggers, animal print on crushed velvet, or an abstract print in bold hues. Whatever you choose, keep everything else subtle and simple to let your pants truly shine. A neutral sweater and a basic trench coat will keep you warm and ensure heads turn as you put your best leg forward!

Find All The Style You Need!

As a stylish and savvy shopper, you probably have tons of winter clothing items in your closet to make these winter outfit styles work. But if you are missing anything to pull an ensemble together, The Willow Tree Boutique is here to help! Browse our collection of best sellers for our most popular pieces, and check out what’s new to stay on top of seasonal fashion!

Have questions about our style guide, sizing, or anything else about shopping with us? Our team is always here to help. Reach out to our friendly, fashionable customer service representatives with any questions for personalized guidance.