What To Wear - January 6, 2021

25 Winter Outfit Ideas + 5 Pieces I can’t Stop Wearing

orange teddy coat, black sweater, distressed levi jeans, leopard pumps and gucci cross body

Winter can easily feel like the trickiest month to get dressed for if you ask me. Between it being freezing outside, shorter days/darker nights, layering, and trying to look cute without looking bulky or frumpy, I thought y’all might like some inspo that I pulled from over the years of winter outfits – both dressy and more casual!

Who knows, maybe seeing some different winter looks will encourage you to switch up your style! Whenever I have no idea what to wear, shopping my own closet or looking through old outfit photos usually gives me some good ideas. Hope this is helpful if you’re in a lull with your winter style or just looking for some winter outfit inspiration! :)

25 Winter Outfit Ideas


Stuart Weitzman OTK boots



faux fur jacket, blush ruffle sleeve blouse, black ann taylor pants, nude pumps, and gucci velvet cross body bag
Jcrew cocoon coat, jcrew winter coat, grey cocoon coat


lake tahoe outfit exploring rocks, hunter boots, jeans, sweater

I love layering a lightweight striped turtleneck under a chunkier one to create a fun and interesting layered look. It’s a good way to mix things up a bit!


all black outfit with cold shoulder top, all black outfit
sportswear lux trend, moto AYO leggings, adidas allstar sneakers, topshop olive green moto jacket, celine phantom bag, casual chic outfit, bomber jacket outfit

Athleisure looks are always a go-to because that’s mostly what I wear each day since I work from home! For more outfit inspiration along the same lines check out my blog post on how to pull off the athleisure look!

Related: Ways to Wear Leather Leggings

high-waisted jeans and blazer

I LOVE a good blazer and turtleneck combo! It’s one of my absolute favorite looks for winter. Great for business casual whether you’re heading into an office or just wanting to put yourself together for working from home. I also love a similar look (swap the blazer for a cardigan) like this winter date night outfit!

burgundy sweater, skinny jeans, white scarf and brown booties
all black winter outfit with western belt and Burgundy suede Moto jacket


green joggers, black sweater, checkered scarf and cap
black jeans, chambray top, black and white striped tee

Get any outfit ideas from these looks?! Which one was your favorite?! I’d love to know!!

5 Winter Pieces I Can’t Stop Wearing

Since most of these outfits are old and can’t necessarily be shopped directly, I thought it might be fun to round up the winter items I’ve been wearing ON REPEAT this season that I think are classic and are winter wardrobe staples. Literally, I can’t get enough of these items and think y’all will love them too!

  1. My short UGG boots – I know, I know… but as far as I’m concerned UGGs are still cool and cute and I wear mine like at least 3x a week, so whoever said they aren’t cool anymore is WRONG. I’m a huge fan!
  2. The J. Crew Cocoon Jacket – This jacket is classic and literally will never go out of style. You can easily pair it with a more formal outfit or wear it daily as your casual everyday jacket. I’ve been wearing my grey one non-stop this winter.
  3. This cashmere scarf – I have bought so many faux/blended cashmere scarves over the years and none of them compare to the real thing. This is something worth splurging on, trust me. If you take care of it, it will last forever and in a classic color like black, navy or white you’ll reach for it year after year.
  4. These Commando leather leggings – I’ve been raving about these for YEARS. I know some people prefer the Spanx ones, and if you’re debating on which to buy, I compared the two in this post. Although, if you’re expecting, Spanx does have a good maternity pair!
  5. This long sleeve comfy tee – I have a lot of really cute tops but I end up wearing the simplest ones in my closet the most because they’re easy to layer with and create new outfits. I love this one by Halogen and have it in the black and then black and white stripes. I think it’s 100% essential to have a crewneck long-sleeve tee for putting together cute winter outfits! I also love this one from Amazon!