6 Shoes to Pair with Straight Jeans

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!

1. Suede Ankle Boots

Levi’s jeans 24w x 26L, Quince cashmere xs, Kenneth Cole boots 5.5 (similar), Naghedi tote in “cashmere,” Edited Pieces coat (not currently available; this one is similar but oversized)

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.

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

petite straight jeans with chelsea boots

Old Navy coat (very similar in petites), thermal turtleneck xxs, YSL bag, Edited Pieces belt xxs, Nordstrom boots 5.5

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.