Autumn foliage has finally been cleared off front lawns everywhere, & we slowly brace ourselves as the cold breeze comes through, reminding us that winter is on its way. In preparation for the upcoming holiday season, thin fabrics are banished to the back of the closet to make room for cozy knitted sweaters, oversized wool scarves, and knee-high boots. If you’re trying to assemble some comfy outfits for winter you’re in luck! I put together a hitlist of must-have staple pieces that will keep you warm & looking stylish all winter long.
While some people tend to thrive in the cold, others can’t help but wonder (sorry not sorry about this Carrie Bradshaw moment): How could one possibly look “cute” when it’s below freezing and one’s just trying to stop one’s body from turning into an icicle? Aesthetic outfits don’t just magically happen overnight – & the key to surviving winter is having a few go-to outfits that you can treat as your wear-everywhere uniform.
If you’re in need of some school or casual workplace outfit inspiration or looking for things to add to your Black Friday wishlist, these comfy outfits for winter are about to solve all of your winter ‘what-do-I-wear’ dilemmas! I’ve put together the ultimate winter 2024 shopping guide (for every type of budget) to elevate your style with outfits you’ll want to wear all the way into spring.
Plus, plenty of the retailers I mention are offering big sales! Let’s dive in!
Welcome to The Style Edit, my weekly series sharing tips on how to create a timeless, pulled-together closet.
1. Matching sweatpants
Pandemic trends may have come and gone (RIP, many, many sourdough starters), but there are a few that never left. One of the outfits that have been gaining notoriety since the lockdowns is the humble sweatsuit.
Although matching sweatsuits are nothing new, they got a total rebrand back in 2020 and elevated our work-from-home wardrobes beyond the “I just rolled out of bed look.” I love a good coordinating sweatsuit outfit, especially one that takes literally zero effort to put together.
For those who are pro-sweats all day, every day, I’ve rounded up a bunch of the best matching sweatsuit sets to shop.
Splurge:
Page Set
Revolve
Lovers & Friends Jogger
2 colors available
Revolve
Save:
Fixmatti Tracksuit Set
22 colors available
Amazon
Linsey Tracksuit Set
17 colors available
Amazon
2. Comfy Athleisure
“What, this old thing? I’ve had it for years.”
Yes, I’m talking about the flannel hanging in your closet. A good flannel is probably the only article of clothing that never goes out of style and the perfect comfy outfit for winter. Good news for us flannel enthusiasts, a good wool flannel only gets better with age. Shop these high-quality wool blend flannels: these shirts by LVIEFENT or these shirts by SHEWIN.
Pair this look with a white puffer jacket for some extra warmth.
Splurge:
Buffalo Check Flannel
Madewell
High-Waist Legging
7 colors available
Alo Yoga
Save:
Wool Blend Plaid Flannel
10 colors available
Amazon
Women’s Yoga Pants
24 colors available
Amazon
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3. Leather Blazers + High wasted light wash jeans + Boots
There are few pieces as timeless as a leather jacket — especially when cooler weather rolls around. You can easily elevate any look in seconds by throwing on a leather jacket, & the best part is your local vintage shop should have a great collection of real-leather jackets from the 90s.
Whether you have a t-shirt or a blouse, adding a leather blazer will give your outfit a layer of sophistication that’s perfect for after-school internships or an afternoon out on the town.
Splurge:
Wool Blend Trench Coat
Sam Edelman
Petite Cali Demi-Boot Raw-Hem Edition
Madewell
Save:
Trench Coat
H&M
Catch Mid-heel Boots
Asos
4. Wide-leg Pants
Cardigans, loafers, converse, and high-waisted jeans are just some of the perennial favorites, but in recent years, wide-leg trousers have quickly joined the list of wardrobe staples we can’t live without.
Give your legs some room to breathe as you sit behind a desk all day with the following stretchy, wide-leg pants. Oh, and although I might have put the wool-flannel and Harlow wide-leg pants in the “splurge” section, they aren’t that expensive; $135 & $118 respectively.
Splurge:
Wool Flannel Trousers
Cos
Harlow Wide-Leg Pants
4 Colors Available
Madewell
Save:
Wide Flared Trousers
2 Colors Available
& Other Stories
Dress Pants
3 Colors Available
H&M
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6. Puffer Jacket
Just like a good pair of walking boots or water-resistant gloves, puffer jackets are cold-weather staples, perfectly blending form and function. A good-quality puffer should be warm and comfortable with a dash of edgy style because, let’s face it, puffer jackets are intrinsically cool.
Splurge:
Rusta puffer jacket
North Face
Noize Felicia-02 Puffer
2 Colors Available
Madewell
Save:
Puffer Jacket
4 colors available
H&M
Women’s Cropped Puffer
26 colors Available
Amazon
5. Loafers
Loafers, oh loafers. These oxford loafers have been trending for a while now and I’m glad they’re still in heavy rotation for winter 2024 and beyond. Zara’s leather loafers literally sell out every time they hit the site, so below are some affordable alternatives that are still in stock.
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7. Hair Clips & Baggy Jeans
Channel your inner ’90s teen angst with this cool-girl denim trend that’s become a street style (or fit pic) favorite. Baggy jeans are a comfy clothing option to help ease you out of your regular rotation of sweatpants.
Splurge:
Freestyle Jacket
Revolve
Straight-leg relaxed fit Jeans
Cos
Save:
Long Sleeve Puffer Jacket
16 colors available
Amazon
Baggy Straight Jeans in Berteau Wash
Madewell
8. Sherpa Coziness
Let’s state the obvious — I couldn’t be more excited that fuzzy sherpas and teddy coat season is on the way.
Arguably, the reliable sherpa is the perfect transitional piece — especially if it’s too warm to wear a parka and a bit too cool to sport the tried-and-true cardigan.
Loving this Sherpa from Abercrombie, & you’re on a budget make sure to check out this sherpa from Amazon.
Splurge:
Multi Pochette Crossbody Bag
Louis Vuitton
Sherpa Shirt Jacket
6 Colors Available
Abercrombie
Save:
Petite flare cord pants
Asos
Sherpa Pullover Sweatshirt
25 Colors Available
Amazon
9. Silk Skirts & Cashmere Layers
Goodbye, uncomfortably stiff denim! Hello flowy, easy-to-style slip skirts.
Historically worn as négligées and as underpinnings for clingy skirts and dresses, the straightforward slip-style skirt is officially considered to be the main attraction this year.
Silk skirts & cashmere make excellent comfy outfits for winter because you can layer them effortlessly. When the weather gets colder, you can wear wool stockings underneath and throw on an oversized sweater to keep warm.
Splurge:
Mock neck sweater
& Other Stories
Maya Midi Skirt
Revolve
Save:
Brushed Belted Coat
Asos
Knitted cable roll dress
Asos
10. Grandma Cardigans & Wide-leg jeans
Cardigans have always had a special place in my heart.
From tweed jackets to vintage-inspired blouses and silk headscarves, grandma dressing is having a major moment on the ’gram, with influencers sporting sartorial gems that look like they could have been stolen straight from our grannies’ closets.
Whether it’s a chunky cable-knit sweater or a sweet knit with floral embroidery and appliqués, cardigans are a fashion-girl favorite, offering endless styling possibilities. They serve as a chic and practical layering piece, making them a natural staple for winter.
Splurge:
Cow Sweater Cardigan
Kulika Cultwear
Cashmere Cardigan
Naadam
Save:
Chuck Taylor
Converse
Super wide-Leg Jeans Madewell
11. Creme-Colored Layers
It’s unusual to see one outfit trend last several seasons. Head-to-toe beige is a staple outfit for the fashion crowd — cropping up both at fashion week and on our autumn/winter 2024 Instagram feeds.
It’s easy to understand why – Tonal dressing using soft colors like oatmeal, biscuit, and blush is a trend that looks elegant and sophisticated. Not to mention a perfect color to add to a minimal closet – beige or creme hues go perfectly with both black and white outfits.
Splurge:
Small Park Suede Tote
The Row
Warren Platform Sneaker
Nordstrom
Save:
Stradivarius straight-leg cargo pants
Asos
Quilted Oversize Puffer
Asos
12. Oversized Sweatshirts & Casual Sneakers
Think: sneakers, jeans, a sweater, and a bomber jacket. Not only is this look ready for a day out, but it has just the right amount of casual cool gal slay for a typical, average school day.
A good, high-quality sweatshirt is your best friend on those days when you don’t want to get up early and put together an elaborate outfit. Pair with a worn in pair of chuck taylors and you’re ready to take on the day.
On top of having a massive fanbase full of actors, models, influencers, and politicians, a classic pair of Chuck Taylor All-Stars ring up at a reasonable $50 ($55 if you’re opting for high-tops). And, the best part of it all? This footwear option mysteriously pairs well with every type of outfit.
Splurge:
Faux Shearling Quarter Zip Pullover
Nordstrom
Glenbrook Half-Zip Pullover
Madewell
Save:
Chuck Taylors
Converse
Oversized Zip Pullover Amazon
13. Faux Fur & Leather Moto Jacket
A jacket that is definitely having its moment right now is the fur-lined moto jacket.
Come fall, everyone needs that perfectly effortless jacket to throw over their shoulders and head out the door. Comfy outfits for winter require statement clothing that is chic, practical, & something that can be dressed up and down. This super trendy faux fur and leather moto jacket is the perfect mix of comfort meets badass.
Shop Fur-Lined Moto Jackets
14. All-black outfits with a neutral-colored sweater
I’ve already mentioned this Sherpa Shirt Jacket by Abercrombie. It’s cute and it’s the type of easy-to-layer sweater that’s so comfy you’ll actually want to live in it for the rest of the season.
Pair this comfy sherpa with black leggings or yoga pants and this really cute t-shirt bodysuit from Amazon.
Splurge:
Nisha Croc Embossed Leather Boots
Saks Off 5th
Valen Pant
Revolve
Save:
Women’s Yoga Pants
Amazon
Chelsea Boot
Madewell
15. Nautical Stripes
In case you missed it, nautical fashion was all over 2024 runways. Refreshing as this trend is, it’s not entirely new: sailor collars and Breton stripes first gained notoriety in the 19th-century war effort, during which there was a growing demand for naval officers. Brenton stripes are the perfect statement piece for those wanting to give hints of “trust fund baby” to their outfit or just looking to add an elevated sense of Parisian luxury to a casual outfit.
Shop Striped Sweaters
Shop My Favorite Staple Comfy Outfits for Winter
Apparis Riley Jacket
Melrose Sweater Jacket
Amber Shoulder Bag
Caroline Jacket
Nanushka Bucket Bag
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