Do you tend to push your dresses to the back of your closet when the weather cools down? Well, no more! This article has all the tips you need for how to wear dresses in winter and during the cooler transitional months.

How to wear dresses in winter: Tips and outfit ideas

Let’s start with some things to consider when choosing the best dresses in winter. After that, we will share lots of stylish winter dress outfit ideas.

1. Choose the right basics

Before we even get onto some dresses for winter and what to wear with them, let’s start with the basics. Dressing in the cooler months is all about layering. These are the layers you should start with to ensure you can wear all your favorite dresses no matter how chilly it is outside.

Opt for a great pair of opaque tights, a pair of black leggings and a camisole. That way, you can ensure your legs are warm, and you can also add a camisole to keep your torso cozy. These layers can form the basis of any winter dress outfit.

No nonsense Opaque Control Top Tights | 40plusstyle.com

No nonsense Super Opaque Control Top Tights

Bandier Center Stage High-Rise Leggings | 40plusstyle.com

Bandier Center Stage High-Rise Leggings

J.Crew Vintage Rib Shelf-Bra Tank Top | 40plusstyle.com

J.Crew Vintage Rib Shelf-Bra Tank Top

Read on for more layering ideas to come!

Also take a look at how to layer like a pro.

2. Get your coat length right

Choose either long or waist length for the most flattering look – nothing in between.

Look for coat lengths that fall just below your dress or that end at your waist. A long coat will create lovely long lines, while a shorter style will create the illusion of longer legs.

Barbour Houndstooth Angelina Wool Coat | 40plusstyle.com

Barbour Houndstooth Angelina Wool Coat

Cinq à Sept Zoe Biker Jacket | 40plusstyle.com

Cinq à Sept Zoe Biker Jacket

How to wear dresses in winter - Tanasha wears a green and pink outfit | 40plusstyle.com

Tanasha @letsrecreatethelook above shows how to get the right length for your longer coats – by choosing a style that is just below the hemline of your dress. We love her pink and green combination!

Steal her look with this similar dress, coat, pumps, handbag and earrings.

3. Shoes for your winter dress outfits

Changing your shoes can obviously make a huge difference to how warm your outfit is. Swap your summer sandals for ankle boots, knee-high boots, sneakers, loafers and brogues. Look for chunky soles – not only are they on trend, but they will stop you from slipping in rainy or icy weather.

Wear over your tights or leggings for added warmth.

Dolce Vita Martey H2O Boot | 40plusstyle.com

Dolce Vita Martey H2O Boot

Naturalizer Deesha Knee High Boot | 40plusstyle.com

Naturalizer Deesha Knee High Boot
(Zappos / Amazon)

COACH Leah Lug Sole Loafer | 40plusstyle.com

COACH Leah Lug Sole Loafer
(Zappos / Saks Fifth Avenue)

How to wear dresses in winter to be cozy and chic | 40plusstyle.com

Emms @beautifuleveryday_uk above opts for a warm sweater dress and knee-high boots in the same neutral color. She adds color with her burgundy bag.

Get her look with this similar sweater dress (another option here), boots and handbag.

How to wear dresses in winter – outfit ideas

Okay, now that you’re thinking about your layers and shoe choices, let’s move on to some outfit ideas for how to wear dresses in winter.

Layered with a turtleneck

Do you have a shirtdress, a v-neck or a lightweight dress that you tend not to wear when the weather cools down? One great way to make it winter ready is to add a polo neck underneath. You can choose a sleeveless sweater or one with long sleeves, depending on how much extra warmth you need.

Layered with a turtleneck | 40plusstyle.com

Mango Snake Print Lyocell DressMango Turtleneck Knit TopNaturalizer Deesha Knee High Bootkate spade new york Market Pebbled Leather ToteLizzie Fortunato The Great Escape Fin 24K Gold-Plate Amethyst Earrings

Knee-high boots with your dress

Knee-length boots look fantastic with a knee-length or midi dress. If you’re putting together an evening outfit, then look for a really special pair of boots like the gold Sam Edelman boots (below).

Knee high boots with your party dress | 40plusstyle.com

Cinq à Sept Khloe Crepe Ruched BlazerCOS Knitted Midi DressSam Edelman Sylvia Knee High BootsTory Burch Reva Leather Clutch-On-ChainChan Luu 18K-Gold-Plated & Freshwater Pearl Pendant NecklaceLizzie Fortunato The Great Escape Fin 24K Gold-Plate Amethyst Earrings

With a moto jacket and booties

Add a moto jacket to your dress and you’ll not only add a stylish edge to your outfit, you’ll also have extra warmth. Look out for autumnal shades for your jacket, like deep burgundies, navy and gray to add a point of difference to your outfit.

Dress with a moto jacket and booties | 40plusstyle.com

Cinq à Sept Zoe Biker JacketAnne Klein Geo Print Long Sleeve Square Neck Midi DressStaud Wally Suede Ankle BootAimee Kestenberg Bali Leather Crossbody BagLizzie Fortunato The Great Escape Fin 24K Gold-Plate Amethyst Earrings

How to wear dresses in winter - Jas wears a dress and moto jacket | 40plusstyle.com

Jas @thefashionstylefile above mixes different neutrals with her moto jacket and winter boots.

Check out this similar dress (another option here), boots, moto jacket, tote and sunglasses.

A short dress with leather pants

A shorter dress is probably the last thing you would choose to wear in winter months as you don’t want cold legs. But, you can always wear your shorter dress with pants or jeans.

A short dress with leather pants | 40plusstyle.com

Mango Satin Wrap DressHudson Jeans Barbara Vegan Leather Bootcut JeansStaud Wally Suede Ankle BootTory Burch Reva Leather Clutch-On-ChainAnabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop EarringsChan Luu 18K-Gold-Plated & Freshwater Pearl Pendant Necklace

With a vest over the top

We’ve looked at wearing a sweater under your dress with the turtleneck option we showed you earlier, but wearing a sweater over your dress is another great option. Choose a sleeveless sweater vest for a preppy look. Make sure the sweater ends at or above your waist for a flattering silhouette.

Dress with a vest over the top | 40plusstyle.com

SweatyRocks Plaid Geo Sweater VestCOS Waisted Midi Shirt DressDolce Vita Martey H2O BootProenza Schouler White Label Large Coated Canvas ToteAnabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop Earrings

Choose a dress with a sweater

AllSaints often have dress and sweater sets, which are a great choice for anytime of the year, as you can wear the dress by itself when it’s warmer, or with the knitwear for a cozy look.

Choose a dress with a sweater | 40plusstyle.com

AllSaints Nadia 2-In-1 Metallic Foil Pleated DressSam Edelman Sylvia Knee High BootsCOACH Canvas Field Tote 22Anabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop EarringsChan Luu 18K-Gold-Plated & Freshwater Pearl Pendant Necklace

How to wear dresses in winter - Cathy wears a sweater over her dress | 40plusstyle.com

Cathy @themiddlepageblog above opts for a sweater over her dress. Note she matches the navy of her sweater to the stripes on her skirt.

Get her look with this similar 2-in-1 dress (another option here), boots, bag, necklace and sunglasses.

With a white shirt underneath

A white shirt goes with everything. If you have sleeveless dresses, you can put your white shirt underneath. Just make sure your shirt is relatively slim so it doesn’t add too much bulk under your dress.

Dress with a white shirt underneath | 40plusstyle.com

Nordstrom Favorite Midi SlipdressPolo Ralph Lauren Silk Classic-Fit ShirtCOACH Leah Lug Sole LoaferCOACH Canvas Field Tote 22Anabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop Earrings

How to wear dresses in winter – With a long coat

Adding a long-length coat over your dress is a fantastic way to keep the elements at bay. Add a scarf, tights, and boots for extra warmth.

Dress with a long coat | 40plusstyle.com

Barbour Houndstooth Angelina Wool CoatCOS Asymmetric Gathered Waist Midi DressStaud Wally Suede Ankle BootProenza Schouler White Label Large Coated Canvas ToteAnabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop EarringsQBSM Large Soft Scarf

With a cardigan

A cardigan is a cozy, stylish way to make sure your dress is warm enough for the winter months. Choose a casual style or a more special cardigan depending on the occasion.

Take a look at these cardigan outfit ideas for inspiration on cardigans that look good with dresses.

Dress with a cardigan | 40plusstyle.com

J.Crew Jackie Ribbed CardiganElie Tahari Leith Cashmere Midi SweaterdressCOACH Leah Lug Sole LoaferCOACH Canvas Field Tote 22Anabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop Earrings

How to wear dresses in winter - Eileen wears a long cardigan over her dress | 40plusstyle.com

Eileen @eileenternullo above chooses a beautiful palette of pastels and gray for her winter dress outfit.

Get her look with this similar dress, cardigan, boots, belt, earrings and hat.

Your winter dress outfits in one capsule

Below, you can see the outfits from above in one capsule. You can see that you can wear the clothes, shoes and accessories in many different ways to create different looks. For example, wear the long coat or the moto jacket with any of the dresses, add the red blazer to the black dress, or wear the brown sweater over the white dress.

Dresses in winter outfits | 40plusstyle.com

Continue reading:

  1. How To Look Fashionable In Winter – Which Of These 11 Ways Do You Use?
  2. The Best Dresses To Hide Your Tummy
  3. Where To Shop For The Best Cashmere Jumpers

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How to wear dresses in winter to be cozy and chic | 40plusstyle.com

Feature image by Emms @beautifuleveryday_uk

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