How I Updated My Winter Athleisure Outfits

My Updated Winter Athleisure Outfits

I was ready to update my winter athleisure outfits, and finally, late one night, I decided to tackle it. I quickly crafted a plan, ordered a bunch of things to try, and landed on a few new pieces that I felt updated my winter athleisure outfits. I don’t wear athleisure often, but my new pieces have changed that! 😄

The first thing I did was look at a small collection of athleisure outfits I’d saved. Then, I quickly analyzed them to look for patterns or common themes and listed the Key Style Elements among them. Here are a few things I focused on and pieces that I looked for…

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes. 


black graphic sweatshirt + black leggings + white and black sneakers + gold jewelry

1. Flare Leggings (Fleece-Lined)
I’d seen this style of leggings on 20 year olds, and it is legit what I also wore when I was around 20. 😆 I was hesitant the first time I saw them and really thought I’d leave this style with the 20 year olds. But just like I mentioned in How My Style Changed, I eventually came around to it and decided to at least TRY these leggings. What’s the worst that could happen? If I didn’t like how they looked, I would just return them – no harm done! Spoiler alert: I dig ‘em! 😄

I specifically looked for fleece-lined leggings since it is currently winter. I’ll go for an unlined pair in warmer weather.

I ordered TONS of different pairs to try! Ultimately, I landed on this BALEAF pair because it has everything I was looking for: has a larger flare, is on the longer side and falls over my shoe quite a bit as opposed to sitting right on top, is NOT super fitted at the knee, doesn’t show VPLs (duh), and has vertical pockets. This pair is SO COMFY and cozy with the fleece lining! The pockets are slightly tapered, which makes it a bit harder to put my phone in all the way, but it’s doable. This pair also has a cross-front waist, which is super flattering. These leggings come in both 29″ and 31″ inseams, HERE. I’m wearing the 31″ pair, and I like how they fold over my shoes with just a slight bend. (But make sure they BEND gracefully at the bottom and not BUNCH as that will look messy). I’m wearing size M.

I originally planned to get a pair of brown flare leggings also, but I couldn’t find a pair I loved. (This pair doesn’t come in brown, or else it’d be a done deal!) However, I think I will hold off on getting brown and see if I wear athleisure enough to need another pair. It IS trending that way though – I like these flare leggings THAT much!


ivory quarter zip sweatshirt + black fleece lined leggings + white and black sneakers + gold jewelry

2. Sweatshirts with Visual Interest
The lack of this type of item has been a hole in my athleisure style. All my athleisure sweatshirts have been basic crewnecks, so I didn’t really like wearing athleisure because I felt my sweatshirts lacked oomph.

For this reason, I focused on sweatshirts with zippers or with graphic prints that have a more structural shape to them, which are elements in line with the Edgy style that I always need a bit of in my outfits. I tried several sweatshirts with zippers and a pocket, which provide more visual interest than a plain crewneck sweatshirt. I landed on the one above, which is really soft, somewhat drapey, and cozy. It has a hood and thumbholes, too! It comes in 16 colors, HERE. I sized up to M as size S felt a tad too short in the sleeve length and whenever I moved around.


brown quarter zip sweatshirt + black fleece lined leggings + white and black sneakers + gold jewelry

I also got this brown one a couple of months ago. It is very thick and warm, though it has more structure than the cream one above. It’s available in 19 colors, HERE. I wear size S.


black oversized graphic sweatshirt + black leggings + white and black sneakers + gold jewelry

Last but not least, I LOVE this California sweatshirt! The bold, block font totally feels like my style and gives the crewneck sweatshirt the oomph I always feel is lacking. It pairs well with jeans and black joggers. So cute! It’s available HERE. I wear size M for a looser and more relaxed fit.

3. Updated Sneakers
The Nike Tanjuns that I LOVE and have worn for many years are great, but they don’t look great with flare leggings. Plus, I think I’m just ready for some updated sneakers. However, they’re more of a “nice-to-have” in my wardrobe at the moment, as my Dolce Vita lifestyle sneakers (that I’m wearing in all the pics above) suffice for most athleisure outfits. I haven’t done a ton of browsing for new sneakers yet, but below are some that I’ve started to look into:

4. Puffer Vests
When I started updating my winter athleisure outfits, puffer vests were on the list. I’ve seen a lot of these vests around again, but this time they are usually oversized. Of course, you don’t need to do oversized if that isn’t flattering! Anyhow, after updating my sweatshirts and getting flare leggings, I felt pretty good about my athleisure outfits and haven’t felt the strong lack of a vest. So, I might skip this one after all.

Even with just the flares and sweatshirts, my winter athleisure outfits feel MUCH more like me and have given me a refreshed excitement for athleisure! Pretty simple!

Shop the Outfits:


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