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 Super Opaque Control Top Tights
Bandier Center Stage High-Rise Leggings
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
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.
Naturalizer Deesha Knee High Boot
(Zappos / Amazon)
COACH Leah Lug Sole Loafer
(Zappos / Saks Fifth Avenue)
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.
Mango Snake Print Lyocell Dress – Mango Turtleneck Knit Top – Naturalizer Deesha Knee High Boot – kate spade new york Market Pebbled Leather Tote – Lizzie 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).
Cinq à Sept Khloe Crepe Ruched Blazer – COS Knitted Midi Dress – Sam Edelman Sylvia Knee High Boots – Tory Burch Reva Leather Clutch-On-Chain – Chan Luu 18K-Gold-Plated & Freshwater Pearl Pendant Necklace – Lizzie 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.
Cinq à Sept Zoe Biker Jacket – Anne Klein Geo Print Long Sleeve Square Neck Midi Dress – Staud Wally Suede Ankle Boot – Aimee Kestenberg Bali Leather Crossbody Bag – Lizzie Fortunato The Great Escape Fin 24K Gold-Plate Amethyst Earrings
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.
Mango Satin Wrap Dress – Hudson Jeans Barbara Vegan Leather Bootcut Jeans – Staud Wally Suede Ankle Boot – Tory Burch Reva Leather Clutch-On-Chain – Anabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop Earrings – Chan 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.
SweatyRocks Plaid Geo Sweater Vest – COS Waisted Midi Shirt Dress – Dolce Vita Martey H2O Boot – Proenza Schouler White Label Large Coated Canvas Tote – Anabel 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.
AllSaints Nadia 2-In-1 Metallic Foil Pleated Dress – Sam Edelman Sylvia Knee High Boots – COACH Canvas Field Tote 22 – Anabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop Earrings – Chan Luu 18K-Gold-Plated & Freshwater Pearl Pendant Necklace
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.
Nordstrom Favorite Midi Slipdress – Polo Ralph Lauren Silk Classic-Fit Shirt – COACH Leah Lug Sole Loafer – COACH Canvas Field Tote 22 – Anabel 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.
Barbour Houndstooth Angelina Wool Coat – COS Asymmetric Gathered Waist Midi Dress – Staud Wally Suede Ankle Boot – Proenza Schouler White Label Large Coated Canvas Tote – Anabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop Earrings – QBSM 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.
J.Crew Jackie Ribbed Cardigan – Elie Tahari Leith Cashmere Midi Sweaterdress – COACH Leah Lug Sole Loafer – COACH Canvas Field Tote 22 – Anabel Aram Ginkgo 18K-Gold-Plated & Cubic Zirconia Hoop Earrings
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.
Continue reading:
- How To Look Fashionable In Winter – Which Of These 11 Ways Do You Use?
- The Best Dresses To Hide Your Tummy
- Where To Shop For The Best Cashmere Jumpers
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Feature image by Emms @beautifuleveryday_uk
Sylvia is 40+style’s editor-in-chief and has been helping women find their unique style since 2011. An alumni of the School of Color and Design, she is devoted to empowering women of any age to look and feel their best. Read more about Sylvia and 40+style on this page.
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I like those lug loafers but styling them with outfits seems impossible. Would love to see more ideas on outfits to go with that type of loafer and heel.