How to Style a Dress and Stay Warm During Winter

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Photo: STYLECASTER | Winter Dress Styling Guide

We have a love-hate relationship with winter. We love cozy layers, sweaters, and boots, but we also miss our flirty shorts, skirts, and dresses from the warmer months. So how do we manage to style our favorite floral mini for winter without completely freezing? The answer is all in the layers.

Layer a classic black turtleneck or blouse underneath your dress, add some tights, a coat (or two), and you’ll be good to go! One of our favorite layered looks is an oversized sweater over a midi or maxi dress; it instantly transforms the dress into a skirted look and feels completely new.

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Layering for winter doesn’t have to be a bulky mess that makes you feel like you’re a walking marshmallow, either—focus on layering with intentional items that you want to be seen, coordinate with the dress, and can be worn all at the same time. Mix and match fabrics and prints, and don’t overthink it. And when all else fails, throw a cozy statement coat over your dress, add some tights and boots, and head out.

MORE: 20 Perfect Fashion Combos That Will Never Go Out of Style

Ahead, we gathered some of our favorite winter dress street styling looks, including a handful of dresses and layering items to add to your closet before the end of the season.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Classic Black Turtleneck

You can easily transform any spring or summer dress into a winter look with a black turtleneck underneath.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Tissue Turtleneck

Turtleneck, $29.50 at J.Crew

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Monochrome

Layer matching OTK boots with a dress for a super-sleek winter pairing.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Velvet Victory

Dress, $133 (was $198) at Rebecca Minkoff

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Long Layers

Our favorite way to wear a dress during winter is by layering an oversized sweater over the dress and transforming it into a long layered look.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Lotus Dress

Dress, $365 at Rhode Resort

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Matching Dress and Pants

Layer matching pants with a dress for an updated winter set.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Oversized Sweater

Sweater, $29.99 (was $59.99) at Mango

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Off-the-Shoulder Pairing

To transition your favorite off-the-shoulder pieces to winter, layer a T-shirt or blouse under the dress for extra coverage.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Off-the-Shoulder Stripes

Dress, $350 at Milly

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Puffer Piece

Double up on layers with an oversized puffer jacket, turtleneck, and slip skirt.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Cable Knitted

Sweater, $130 at Everlane

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Fishnetted

Layer fishnets, over-the-knee socks, and multiple jackets with your mini dress.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Golden Number

Dress, $264 at Revolve

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Make Each Layer Count

When opting to ditch the large winter coat, make sure to make each layer count. Add a decorative blouse, fishnet tights, a hat, and even a couple of hidden layering pieces for extra warmth.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Lace Top

Top, $345 at L'Agence

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Blouse Things

Dress up the look and add a blouse under your dress. Look for a blouse with decorative sleeves, volume, or patterns for that extra punch.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Diamond Sweater Dress

Dress, $348 at Kate Spade

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Long-Sleeve Layers

Brighten up your look by adding a colorful long-sleeve tee under your dress.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Mesh Maxi

Dress, $75.50 (was $108) at ASOS

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Red All Over

When in doubt, go for a monochromatic look. You can bulk up on layers, and it will still look super chic when it's all one color.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Print Mix

Dress, $299 (was $598) at DVF

STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Patchwork Dress

Dress, $450.45 (was $495) at Ulla Johnson

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Statement Coat

A simple way to stay warm but not feel weighed down with layers is adding a simple statement coat!

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Lace Up Sweater

Sweater, $51 at ASOS

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Blazer Layers

Switch out your coat for a long tuxedo blazer as an extra layer.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Pearl Embellishments

Dress, $3,150 at Stella McCartney

STYLECASTER | How to Style a Dress and Stay Warm During Winter
It's a Tights Party

Don't forget about your tights! Add a colorful pair when you want to spice things up.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Universal Bodysuit

Bodysuit, $48 at Free People

STYLECASTER | How to Style a Dress and Stay Warm During Winter
OTK Boots

Pair over-the-knee boots with any dress for an instant winter update.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Oversized Boyfriend Sweater

Sweater, $69 at Urban Outfitters

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Printed Layers

Mix prints for the ultimate winter layered look.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Crochet Maxi

Dress, $526.66 at Self-Portrait

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Puff Sleeves + Piping

Dress, $129.90 at Eloquii

STYLECASTER | How to Style a Dress and Stay Warm During Winter
Colorful Layers

Add a colorful or contrasting cropped jacket over your dress.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Floral Frenzy

Equipment dress, $147 (was $490) at Net-a-Porter

STYLECASTER | How to Style a Dress and Stay Warm During Winter
The Sweater + Dress

A simple sweater will add extra warmth and dimension to any dress.

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STYLECASTER | How to Style a Dress and Stay Warm During Winter
Palm Wrap Dress

City Chic dress, $119 at Nordstrom

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  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter
  • STYLECASTER | How to Style a Dress and Stay Warm During Winter

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