How to Wear Dresses in the Winter

Have we reached the point of the year where everyone is slowly transitioning their mindset to Spring fashion? I’m a bit torn between the two seasons, but I know a lot of people who live in cooler climates get a bit antsy for the spring as we close out January. Personally, I love the cooler weather here because I can comfortably layer up, but I also want to incorporate early Spring silhouettes.

What better way to put a little spring in your winter step than with a dress? Today, I’m sharing 5 ways you can incorporate dresses into your winter wardrobe.

topshop snakeprint dress with boots outfit

What I’m Wearing || Dress: Topshop | Boots: Steve Madden | Sunglasses: Life by Her | Coat: Pretty Little Thing | Watch: JORD (enter the giveaway!)


5 Ways to Style Dresses in the Winter

Double Up with a Skirt

Are you ever in the middle of trying on clothes and accidentally put a killer outfit together? This totally happened to me yesterday, which made me think of this styling tip: double up on your dresses in the winter!

Sometimes all you need is an extra bit of lining in your dress or skirt to feel warmer. In the winter, don’t be afraid to stack your bottoms. I mixed prints by layering a leopard print maxi skirt on top of the snake print maxi dress featured in today’s post and absolutely loved the outcome. Not only did the extra layer feel like it could withstand cooler weather (even with the split), but it was a fun way to further style my dress.

Your dresses don’t have to remain in the closet until the sun comes out. Instead, try layering a skirt over your dress to split up the look. If you want to full dress to be the focus, you can wear the skirt underneath like a slip!


how to style snake print

Swap Sandals with Tall Boots

Dresses are so often paired with sandals because of the spring/summer season, but they also look stylish with boots. In the fall and winter months, you can take advantage of this pairing and reach for your tallest boots to keep your legs warm.

As a general rule of thumb, the shaft of the boot should adjust based on the style of dress you’re wearing. The shorter the dress, the higher the shaft.

  • If you’re wearing a dress that stops above the knees, opt for a thigh-high or over-the-knee boot.
  • For midi dresses, finish the look with a knee-length boot.
  • Maxi dresses have the most flexibility and can be styled with ankle boots.


styling red boots

Top it off with a Sweater

Often times, our favorite dresses are sleeveless and/or have a shoulder-baring neckline. To wear your favorite dress in the winter, layer up with a sweater. The sweater on top of the dress transforms the outfit to a top and skirt combo, giving you an additional way to style your dress and change the look.

For the best fit, pick a sweater with a relaxed fit that falls comfortably on your lower waist. If the sweater doesn’t have a bit of stretch at the hem and instead falls freely, a cropped option will keep your outfit from looking frumpy.


pretty little thing red coat

Add a Pair of Tights

Tights have quietly rebranded themselves to fit in with the modern style. Gone are the days that tights would only be associated with business attire. Now, you can pick different colors and patterns to match your personal style. Keep your legs covered while wearing a dress in the winter with a fun pair of tights!


topshop snake print dress

Style it with a Long-Sleeved Tee

Lastly, you can style a dress in the winter with a turtleneck or long-sleeved tee. Instead of layering on top like with the sweater option, the tee is styled underneath your dress a la 90s fashion. For the best look, pick a fitted cotton tee in a neutral color. This layering option is ideal for spaghetti-strap or strapless tops, but don’t be afraid to experiment and find your favorite pairing.


style dresses in the winter

To recap, below are the 5 ways you can style dresses in the winter:

  1. Double Up with a Skirt 
  2. Style it with Boots
  3. Layer on a Sweater
  4. Add a pair of Tights
  5. Pair it with a Turtleneck

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