I’ve experimented with a range of denim styles this year, but my “safety” is still the slim straight ankle jean. I just find this cut to be the most universally flattering as well as practical for me, since it’s the easiest style to pair with flat shoes. The Levi’s wedgie straight (reviewed here) and Abercrombie ankle jean (I wear the 24 Short) are my 2 favorite options in petite-friendly sizing.
I always get questions on what shoes to wear with these ankle-baring jeans in the winter, so below are a few options that will still keep your ankles warm! This Instagram video also shows each of the shoes and pairings.
1. Suede Ankle Boots
This is my top footwear choice with such jeans in the winter since it’s very comfy, provides coverage, and can be dressed up or down. After wearing these booties comfortably around town, I have to admit I went back and got the black and mushroom as well. I’m between 5 and 5.5 in most brands, and needed the 5.5 in these.
While I’d personally love a sharper toe shape (either a little more square, or a pointy toe), it’s just so rare for me to find shoes this comfy that aren’t sneakers. I tried the Everly, Emilie, and Ella styles on and all are super similar. These are a little hard to find in stock now, but I’ve seen occasional restocks at Nordstrom, Bloomingdales, Macy’s and Amazon.
2. Chelsea Boots
I bought my Miller chelsea boots many years ago and they’ve served me extremely well! I was surprised to see them still available here – they look exactly the same from photos, but I can’t be sure whether they’ve made any changes. The Sam Edelman Laguna is also popular and similar with a higher shaft that’s a little easier to tuck inside jeans.
3. High Top Sneakers
4. Sneakers
Both the jacket and sneakers are old pieces that I dug out and happen to still be availble! Abercrombie also has a great similar jacket that’s cozy lined on the inside, too. You can see the same sneaker in my recent outfit post with a tweed jacket for a smart casual look.
To keep ankles warm, it’s conveniently now on-trend to wear socks with sneakers and ankle jeans, as long as it has a little color contrast with the shoe. I’ve seen a light gray sock most commonly around the city, worn with sneakers like this or Adidas Sambas.
5. Loafers
Like with sneakers, to keep ankles warm I’ve seen many stylish ppl wearing loafers with a slightly contrasting sock, like brown, gray, or navy.
6. Ballet Flats
Hi Jean where are your sunglasses from in the Sneakers pic?
Hi Andie, those are the Thierry Lasry “lively” style. I got them many years ago from Shopbop and they’re still a favorite!
High tops and Chelsea are looking great.
Thank you!
love your style
Love the outfits
Thanks so much Regina!
How does the gap sweater tunic fit? Did you get PXS? It’s adorable but hesitant that it will swallow me
It’s definitely a looser wide cut fit but that’s the style of these tunics! I have the sleeves cuffed up once as you can see. I’ve been liking it and it’s easy to throw on with leggings or slim black pants, too.