Winter Fashion Favorites: The Best 25 Pieces of The Season

The holidays are over, the halls have been un-decked, and quite honestly, we need a little pick-me-up.

Winter dressing in November and December versus January and February always feels a little different to me, despite the weather being similar. It’s less cozy and inviting and more “let’s power through this and get to spring.”

But despite the post-holiday sadness and lull of going back to work, winter dressing can be exciting — and honestly, this could be exactly the time to pick up a few things to give you some dressing inspiration.

We’ve rounded up 25 of our favorite items available this winter — from basics we swear by to trendier pieces that can be easily incorporated into your day-to-day wardrobe. Don’t wish for spring just yet.



1. A Faux-Fur Statement Coat

We’re constantly on the quest to somehow look chic and warm simultaneously, and this winter, the fashion Gods brought us the fur and teddy trends — both of which help you stay toasty without looking like a marshmallow.


2. A Twist on Leather

In a spin on the classic leather jacket, leather puffers and pants are everywhere this season. Edge up your outerwear with a faux-leather bomber or blazer:


3. A Beret

The French’s impossibly chic go-to headwear is all the rage this winter, and it’s easier to wear than you’d think. Slip it into rotation with your pom hat on days you’re feeling a certain, how do you say, je ne sais quoi.


Wool-Blend Beret

7 colors available


4. A Long Puffer

Sometimes comfort comes before style, and we respect that; but luckily, extra-long puffers are in this season, proving that the fashion Gods have the next polar vortex in mind. (I can’t get something with “sleeping bag” in its name on my body quick enough.)


Re:Down Sleeping Bag Puffer

3 colors available


5. A Go-To Headband

For the past few months, hair accessory trends have made it impossible to have a boring ‘do. Having a go-to headband is a winter 2020 essential (yes, you can pull it off).


Twist Headband

2 colors available


Satin Knot Turban Headband

5 colors available


6. Something Houndstooth

The preppy pattern is competing with long-reigning animal ones for our favorite print of the season. These trousers or this skirt would be the perfect addition to your winter wardrobe, as they can be worn with all your basics for a trendy twist on your go-to jeans.


7. A Midi Sweater Dress

A sweater dress isn’t new nor exciting, but a super-soft midi one with balloon sleeves? Count us in.


Knit Turtleneck Dress

2 colors available


8. Basic Sneakers

White sneakers aren’t only designated for spring and summer. From errands to happy hour, these will be your most-worn shoes.


9. A Wear-Everywhere Camel Coat

This one doesn’t need too much explaining. Is there anything more flattering than a camel coat? I think not.


10. Modern Booties

Our staple black booties will always be front and center in our closets, but we love this modern, wearable take on plainer pairs. There’s nothing you can’t wear them with.

Steve Madden

Davist Bootie

3 colors available


11. A Bucket Bag

If you’re looking for a bag that’s both practical (looking at you, mini bags) and on-trend, look no further. A bucket bag can fit all of your things and look damn good while doing it.


12. A Cropped Cardigan

Let your longer cardigan take a rest and give this season’s cropped version a try. By “cropped” we don’t mean your belly button needs to be out; these are the perfect length, hitting right at the top of your jeans.


13. The Perfect Sweater

Everyone needs a warm, well-made, go-to sweater, and this one fits the bill.


Fairbanks Pullover Sweater

2 colors available


14. A Layerable Long-Sleeve Tee

Everyone needs a long-sleeve tee to easily layer under jackets when it’s chilly. This one is ultra-soft and ultra-flattering.


15. The Perfect Pom Hat

Stay warm while looking adorable — this is a need, not a want.


Ribbed Pom Beanie

7 colors available


16. Knee-High Boots

As much as they’ve kept us warm throughout the years, our OTK boots have sadly been replaced by their lower-cut sister — and we’d dare call these ones perfect.


17. A Teddy Coat

Yes, everyone and their mother has a teddy coat this season, but that doesn’t mean you shouldn’t too.


18. A Statement Bag

Everyone needs a bag that does the talking when the rest of you is sporting five-year-old jeans and your coziest turtleneck — and this bag is it.


19. Your Gold Hoops, Updated

Basics adorned with pearls was one of 2019’s most commonly seen trends, and we love the femininity that anything pearl brings. These aren’t your grandma’s pearl earrings, but an imperfect, hooped version that you’ve probably seen on Instagram time and time again. They’re the perfect way to up any outfit.


20. Faux-Leather Pants

Our editors have been singing the praises of the Spanx leather leggings for months on end, and while they’re a weekly staple that isn’t going anywhere for us, different versions of the leather pant do also exist. This season, leather on leather is an edgy and acceptable combination, and these leather trousers will leave you feeling like a chic businesswoman instead of Sandy. (Bonus points if you pair them with the leather puffer above).


21. A Statement Blazer

Yes, suiting is still in — and these? *Italian chef kiss*


Faux Leather Blazer

2 colors available


22. A Statement Sweater

Don’t worry, neutral lovers — we’ve got your back. Colorblock is everywhere this winter, so if you don’t want to make a statement with something brighter, this is the perfect way to make a statement within your comfort zone.

If you aren’t afraid of a little color, this brighter option in one of the season’s hottest hue combinations.


23. Patterned Loafers

We’re all about a classic pair of loafers, and this leopard pair can’t be beat. Pair them with literally any outfit (yes, even ones with other patterns!) to make you kiss your go-to black ones goodbye.


24. A Top with a Statement Sleeve

I’m to the point that more items in my wardrobe have puffy sleeves than don’t, and it’s for a good reason. The trend makes you look super feminine and gives any outfit a little something extra. If you’re a cold-shoulder top lover, try this instead, and thank me later:


25. LBBs (Little Black Booties)

Still haven’t found your perfect black bootie? Meet your new best friends:

Chinese Laundry

Davinna Bootie