Wearing Dresses in Winter: 5 Style Tips to Consider

How to Wear Dresses in Winter

Dresses and winter aren’t typically a pair that go together when thinking about cold weather styling. I’ve been going through my dresses in preparation for some warm spring getaways, and in doing so I realized how rarely I reach for them once temperatures drop.

While a sweater dress is the obvious cold weather dress of choice (I’m a fan of wintery white ones), you can up the ante and give your non-knit dresses some wear with a few low-effort styling tweaks.

The goal? A finished look that’s equal parts chic and warm. To that end, see below for five simple ways to wear your dresses in winter.

How to Wear a Dress in the Winter
Tips for Wearing Dresses in Winter

How to Wear Dresses in Winter

1. Add Tights for Warmth

While midis and maxis usually provide enough warmth for the lower half, black tights are a must for a mini dress. I’ve tried several brands and my top two favorites are Falke and Commando. An easy formula I recreate again and again is a mini dress with tights, a faux fur jacket, and tall boots. If it’s particularly cold where you live, try fleece-lined tights, Shapewear leggings, or faux leather leggings and swap in a longer coat.

2. Full Coverage Boots

Tall boots as opposed to ankle boots or booties are just one more option to add warmth to your lower half. My knee-high boots and over-the-knee boots get the most wear with dresses by a landslide. Go with block heel or flat boots for casual outings and stiletto tall boots for dressy ones. My over-the-knee boots are typically reserved for date night as they tend to read a little sexier, as seen in this Stuart Weitzman OTK boot review.

3. Layer a Sweater

If you live somewhere with mild winters, this can be an easy go to. While there are hundreds of dress and sweater combinations, this is usually done best by layering a printed dress underneath a coordinating solid sweater (or vice versa). For a dressier take, I love layering satin dresses underneath chunky knits or cashmere for a luxe feel. Cropped sweaters work best, but you can try one of these belting techniques with a full length knit.

4. Layer a Winter Coat

Outerwear is the element of a cold-weather dress look that makes it a decidedly winter moment. Oftentimes a long teddy or wool coat is all that’s needed to make a dress winter ready! Mixing a moody floral dress with a layer (it could even been a wool blazer, leather jacket, or thick cardigan) is one of the classiest combos. Reach for tall boots and make it yours with accessories.

5. Wear a Turtleneck Underneath

This is a simple winter outfit that’s a little more fashion-forward and works especially well with mini dresses and slip dresses. I’ve seen this pulled off beautifully for holiday parties, date nights, and other winter events when the majority of the time is spent indoors. As long as you have a coat to keep you toasty to and from wherever you’re headed, this is an unexpected way to give your summer dresses more life in the colder months.

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Tights and Dress Winter Outfit
How to Wear a Dress in Winter