How to Wear a Skirt in the Winter (Without Freezing)

While dressing for the holidays can certainly be fun, I feel a bit differently about cold weather outfits when it’s the dead of winter (and it’s nothing but dreary outside.) With that being said, I know I’m not alone in feeling tired of wearing jeans on repeat. Contrary to popular belief (or your personal comfort zone) pants aren’t the only bottom option that work for winter wear.

With a little bit of planning and effort and a good amount of layering, skirts are a fun piece to incorporate into your winter wardrobe. Pieces like tall boots, tights, and long skirts make it possible to pull this look off in even the coolest of climates.

Need some specific outfit inspiration? Here, I’m sharing a handful of ideas for how to wear a skirt in the winter. These looks would work for a variety of outings and occasions, and you could easily add tights or stockings underneath and of them for some extra warmth!

How to Wear a Skirt in the Winter

Watch Here: A Simple Way to Style a Skirt in the Cold Weather

Opt for tall boots.

If you’re hoping to style a mini skirt during the winter, my best tip is to be smart about your shoes of choice. While I love the combo of a skirt and heels or ankle booties, when the temps turn more toward the brutal side, tall boots are often the best footwear pick. The more you can cover your legs, the warmer you’ll be.

These knee high boots have been a longstanding favorite of mine. They are an investment but they pair well with everything and are truly designed to last a lifetime. You could also go with over the knee boots on particularly cold days. And as always, adding tights is an option.

Wear a skirt with a chunky knit sweater.

The original inspo behind this winter white outfit was to create a crisp and cool holiday party look. While it certainly has a festive feel, it proves that wearing a skirt in the cold weather can be as simple as getting smart about the other pieces you put on. The tall boot and chunky sweater duo will ensure you stay warm up top and on the bottom.

Sure, you might have some skin showing…but if you need some additional warmth, a long wool coat would do the trick!

Go with a midi or maxi skirt for more coverage.

One of the best ways you can get away with a skirt outfit for the winter? Going with a piece that offers some length. Again, the more coverage, the better — especially when you’re dressing for those mid to late winter months.

Here, I styled one sequin midi skirt in four different ways. This specific skirt is under $70 and is the ideal length to pair with a variety of shoes (heels, ankle booties, tall boots — you name it.) It’s also a piece that’s easy to wear from day to night. Style it with a cardigan and a coat, a bodysuit and a leather jacket, or a crewneck sweater and a faux fur layer.

Don’t forget to layer.

Preppy and fun, this outfit would actually work for fall, winter, and spring wear. When dressing for the cold weather, most of us think of layering on top of other items — but don’t forget that some pieces provide the option for layering underneath.

The exact sweater I’m wearing below is nearly sold out, however, any knit that’s roomy should allow you to layer underneath it. A long sleeved tee or a thermal shirt would be perfect underneath an oversized sweater. This trick is one of my go-to’s since it means you can take your top layer off if you do get warm.

Tuck a cashmere sweater into your skirt.

I have always loved the look of a French tuck, and this trick just so happens to work perfectly when styling a skirt with a sweater. I’ll let you in on a little secret: the dark brown sparkly number I’m wearing below is actually a dress (but it’s so cute I had to include it in this blog post.) To achieve a tucked in look with a sweater and a dress, use a belt! It’s a tried-and-true hack that I’ve been utilizing for years.

Add a wool blazer on top.

One underrated layering piece? A classic blazer. This one is made with a wool-blend material so it actually is quite warm and cozy. I’d recommend sizing up if you want a more trendy fit! Underneath, I’d go with a simple long sleeved bodysuit or a sweater. And for shoes, boots of any height would work (depending on what the weather calls for.)

This look is sophisticated and timeless, making it a nice option for more formal dinners, a winter date night, or a work party.

Which winter skirt oufit is your favorite? Let me know in the comment section below!