Ask a Stylist

Q: Can I wear socks with ankle boots & cuffed jeans? Or, is this a fashion no-no? – Jacky

We’ll be the first ones to say that the most contentious pairings often stem from socks. Socks with sandals, anyone? Didn’t think so. But socks with ankle booties? We say, yes.

Here’s how to style socks with your ankle boots

Stitch Fix Women's model wearing navy pullover, navy fair isle hooded cardigan, grey socks over her blue jeans and brown combat booties.

Wear with: Cuffed Jeans

We taught you how to cuff jeans, now let’s move on to wearing your cuffed jeans with ankle boots and socks. Once you cuff your jeans, let a patterned sock peep out from the top of your ankle booties. Make sure that you tuck your socks under the cuff, not over.

Wear With: A Shirt Dress

If it’s warm outside, but not warm enough to leave the house without some sort of extra layer, try out a shirt dress with socks and ankle boots. Rule of thumb here, don’t let more than 2-3 inches of your sock peek out over the top of your ankle boot.

Wear With: Tights

If it’s a little cool outside, reach for a pair of tights and don’t hesitate to layer on socks with ankle boots. For a monochromatic look, try out black tights with black socks and black ankle boots.

One final tip: The key to pulling this trend off successfully is to pull your nicest mid-calf socks out of the drawer (not your gym socks) and head out the door with your ankle booties.

—Anne

Need a pair of ankle booties to complement your socks? Take your style quiz and let your stylist send you the perfect pair when you schedule a Fix. Keep what you love and send back what you don’t. Shipping and returns are always free. Now that’s an offer that will knock your socks off. 


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