In this episode, I answer the question a lot of women have asked: “How do I wear ankle booties in the winter?” We all want to be fashionable, but not frostbitten–is it possible to have both? I also tackle the sock conundrum, and share when you should keep them hidden, and when you should let them show.

Links & Resources from the show:

Visit Holding Hangers and use STYLE15 to take 15% off of your first purchase. They’re seriously revolutionary!

The Style Lounge has closed. We invite you to join our member community in The Style Circle.

Grab your FREE Mini Capsule Wardrobe Guide, and make 30 outfits out of just 10 pieces.

Have a question you’d like answered in Office Hours? Email

Listen to the Episode Now:

Stitcher    Spotify    Apple Podcasts

**This post may contain affiliate links, which means, that I may receive, at no cost to you, a small commission from purchases made through links we provide. Thank you for your support.

Read the full episode transcript below! – Ep 30 How Do I Wear Ankle Booties In the Winter?

Today’s episode of Office Hours is sponsored by one of my very favorite products, Holding Hangers. You’ve heard me talk about this one before, in our episode of Editing Your Closet Like a pro. I shared what a big difference great hangers make in keeping your closet organized, and Holding Hangers are unlike any hangers out there–instead of clips or clamps to hang on to your pants and skirts, Holding Hangers use gentle tension inside the waistband to hold your garments, so there are no damaging marks on your clothes. And unlike folding your pants over a hanger, which causes major wrinkles, Holding Hangers allow you to keep your items hung crease-free so they’re ready to go when you are. No last-minute steaming required! Everyone should have a set–or two-of Holding Hangers in their closet, and Everyday Style listeners can take 15% off their first purchase by going to and using code STYLE15. That’s STYLE15 in all caps. I know you’re going to love them as much as I do.

Welcome back to Office Hours–the weekly show of the Everyday Style School podcast, where we answer one question, submitted by you, to help make style easier, and getting dressed more fun.

Today’s question has been asked by literally dozens and dozens of people over the last couple of years, so I thought it warranted an episode of its own.

The question everyone wants to know is “How do I wear ankle booties in the winter?” Usually, this question includes some reference to not wanting to show skin, or not wanting to freeze your skin or confusion about socks.

If you’re a regular listener, you’ll know that I touched on this in episode 16, when I answered some frequently asked shoe questions, but for women new to the show, or looking for a quick answer, here it is.

Keep in mind that this episode is current as of February 2020. If you’re listening to this episode years from now, first of all, hello future lady! But also, trends and styles change, and you should check to see if this is still true.

Alright–Ankle pants and ankle booties are 2 trends that have become commonplace over the last couple of years, we see them everywhere now–and in a perfect world, they would pair well together. And, in some situations, and some climates, they do. But, getting the height of the bootie and the length of the pant right can be super tricky and all bets are off when you live in a freezing cold climate and aren’t a fan of frostbite. But, for the last few years, at least when it comes to pants, ankle pants have dominated store inventory, and it’s been tough to find alternatives, making winter a challenging season to get dressed.

When it comes to dress pants and booties–like for an office situation, socks are not supposed to show, you’re supposed to see a sliver of skin between the bootie and the pant hem or have the hem long enough so that it comes down over the shaft of the boot, creating an intentional high water look. This last one works best with a straight leg pant, not a skinny silhouette.

If showing that sliver of skin is unthinkable, and you hate the look of a cropped pant over a bootie, your best solution is to wear full-length pants that go over the bootie. You’re in luck because there are a lot more options out now, making this much easier.

Now, I know there are women out there thinking–whatever, I just wear socks–who cares?. And while I respect the right of every woman to mess up a perfectly good outfit, I’m simply answering the question I get asked. If the question was, “Can I wear socks that show with my dress pants and ankle booties?” My answer would be? “Absolutely you can. You should do what works for you”. But if you’re asking how they’re supposed to be worn, it’s without seeing socks.

Casual pants are a whole different story. Fun socks are having a moment, and are meant to be seen—again. In a capsule outfit this look is meant to be intentional. We’re not talking about showing 2 inches of black trouser socks or letting your white ankle socks peek out. Socks with jeans or other casual pants and ankle booties are an accessory, and I’ve found myself choosing shorter jeans, or cuffing my longer ones this winter to show more sock. We even have a thread in the Capsule Community–shout to my capsule subscribers!–where we show how we’re styling socks and booties. Again, have fun with this, but make it look intentional. Lastly, if you have a bootie with low cutouts on the side or perforations that show through–save those

While I have your attention, let’s talk about socks and other kinds of shoes. When it comes to flats or loafers socks are not meant to be seen. So if you’re wearing a shoe with a low vamp, like a ballet flat, skip the socks. If that’s not an option with your weather, pick a different shoe. A good alternative would be a loafer or an oxford that has a higher vamp and would cover most of the top of your foot, and your socks. Worn with straight leg or wider pants, you can wear socks, and keep your feet toasty.

I hope that clears up the sock conundrum once and for all. If this has been a challenge for you, don’t worry, wider leg pants are coming back, and showing skin won’t be as big of an issue

Once again, I’d like to thank Holding Hangers for sponsoring this episode, and don’t forget to head over to and use code STYLE15 (all caps!) to take 15% off of your first purchase

If you’re listening, and have a question you’d like me to cover in Office Hours, email it to

That’s all for today–see you next week!

Are you on the list? Sign up now to get a Style Tip and Product Pick every week, delivered right to your inbox!

Similar Posts