Dresses are one of the most versatile pieces you can have in your wardrobe. Similar to women’s designer jumpsuits, there’s nothing like the ease of slipping a dress on to wear with sandals for a convenient and fashionable ensemble. Though warm, sunny weather inspires our usual dress-wearing days, you don’t have to pack them away come winter.
With a few layering pieces and the right shoes and accessories, you can continue wearing your favorite spring and summer dresses all year long. We’re sharing a few of our favorite styles and tips for how to wear short and long dresses in winter when the temperatures start to dip.
Agnes Long Dress + Brown Bomber Jacket
If there was ever a color palette that edged the seasonal cusp, the Agnes Long Dress is it. The warmer hues of pink, blue, and orange are equally suited for the dog days of summer and work well just as well into the early winter months.
We love the playful, multi-striped fabric and unexpected color combination for any season. Pair with a cropped, brown bomber jacket and matching knee high brown boots to give the dress an urban appeal and make it more suitable for the cold weather.
Agra Bia Long Dress + Cozy White Cardigan
The color, fabric, and style of the Agra Bia Long Dress exude a soft, romantic vibe. Purple is a gorgeous color for the winter and a cozy white cardigan makes for the ultimate pairing. The blue exotic details work as built-in accessories for the dress and the scalloped hemline and functional tie in the front add elements of style.
Play up the coziness of the dress by wearing it with white- or neutral-toned- Mukluks or opt for gold flats for subtle shine. Part of learning how to wear summer dresses in winter is adding different textures and warmer materials as a layering piece.
Bandhani Red Zoe Slip Dress + Cropped Denim Jacket
The warm, golden tone of the Bandhani Red Zoe Slip Dress is a perfect color palette for fall that can be taken into the winter months as well. The Indian-inspired print is universally appealing and works well when paired with different types of jackets. A cropped denim jacket keeps the look casually cool and ready to wear for any weekend outing.
The deep front slit of the dress is what makes this the ultimate summer dress. Though you can transition wearing it for winter by pairing the look with knee- or thigh-high boots or adding a pair of lightweight tights and wearing ankle boots instead. The feminine features of the dress, such as the draping neckline and silky material, works well with the androgynous appeal and structure of a denim jacket. Complete the look with the Red Ball Necklace and simple gold earring studs or hoops.
Rajah Kate Midi Dress + Silky Black Blazer
The Rajah Kate Midi Dress is a timeless piece that is ideally suited for any special occasion. The flattering silhouette combined with the modern cut and snakeskin print makes it a go-to outfit regardless of the season. Despite the thin parallel straps and subtle front cutout, which speaks to summer, a few added accessories can make it winter-ready.
Add a silky black blazer and closed-toe black pumps for an elegant look. Then, add on gold accessories, like the Tulip Earrings or dangly diamond earrings for a glamourous finish. And, for a fashion twist on streetwear, swap out the black pumps and wear the midi with fishnet stockings and moto boots instead.
Experiment with the vibe you want to achieve depending on where you’re going to wear the look. You can go from sexy and sophisticated to edgy and cool with little effort at all.
Kimi Yana Midi Dress + Button-Up Shirt
An animal print works for every season and the Kimi Yana Midi Dress can easily take your summer look into winter. The warm-toned cheetah print is trendy yet timeless. Whenever you have neutral tones to work with, there are numerous ways you can change up a look. The high slit, bustier top style, and fitted structure all come together beautifully in the dress.
Though the sophistication of this midi is designed for a special occasion, you can also dress it down for a casual weekend look as well. Layer on a button-up black or white shirt and tie at the midsection for a laid-back yet polished look. Pair with chunky black heels or boots for a cute brunch-ready or date outfit. Complete the styling with topaz earrings and a few delicate gold necklaces.
Winnie Long Dress + Shrug Jacket
The artistic floral print of the Winnie Long Dress mixes the warmth of red and orange with pops of green and violet. The wrap style and lightweight material are flirty and feminine, perfect for a summer evening. However, it can be transformed into a wintertime outfit with a few wardrobe layering essentials.
A shrug jacket over the shoulders adds a needed layer to protect against the cold without taking away from the design of the dress. Sticking with a neutral color keeps it from competing with the colorful print. Also, adding similarly toned opaque tights and knee high boots provide extra coverage while pulling the outfit together for a complete look.
A chunky scarf adds another texture as well for additional neck and chest coverage as needed to fight off the winter chill. Essentially, building fashionable layers around the dress allows this stunner to work even as days and nights grow colder.
Cher Dress + Gold Sequined Blazer
As far as go-to dresses go, the Cher Dress is an instant showstopper. The deep rust hue and metallic gold reflective thread add the right amount of shimmer to this ankle-length dress. The fabric blend also flows smoothly along the body, creating a flattering silhouette. For added sparkle, pair with a gold sequined blazer that skims the thighs.
The gold pulls out the natural shine of the dress and takes it to another level. It’s a beautiful look for any holiday celebration, especially winter weddings. A crisp white blazer also pairs well with the dress for a night out. Avoiding white after Labor Day is a fashion myth and can actually add a welcome pop of brightness to a warmer dress tone. Pair with stilettos or kitten heels for a sophisticated and festive look.
Fiorella Black Lolita Dress + Cropped Moto Leather Jacket
The trendy zebra print of the Fiorella Black Lolita Dress is fun and flirty. It’s a fresh take on the classic black and white color palette with extra stylish design elements woven throughout. The two front slits give the skirt movement, and the wrap end gold detailing adds hints of sparkle to the dress.
To maintain a modern appeal, layer on a cropped moto jacket. A moto leather jacket instantly adds an edge and changes the aesthetic of the dress. Pair with black tights and mid-calf boots to play up the style or switch it up and pick a pair of structural heels instead to echo the eye-catching design.
Finish with simple silver accessories like a solid necklace chain and/or stud earrings. Whether you want to keep the look soft and simple or modern and a little bit grunge, this dress is versatile enough to do it all.
Mamba Luna Long Dress + Boyfriend Jacket
Upon first glance, the vibrant yellow of the Mamba Luna Long Dress may seem too sunny for coldweather. However, what better way to perk up the gray days than with a bright spot like this stunner? The snake-inspired print adds texture to the dress and the front slit allows for easy movement. Sometimes it’s the unexpected that makes for the best fashion.
To wear during the winter, pair the maxi with a camel-colored boyfriend jacket. A slightly oversized layer delivers a relaxed, weekend look ideal for a lunch date or a farmers market stroll. For added definition at the waist, add a brown belt and then match it to the shoes. Either tan or brown moccasin boots pair well with this outfit and keep the feet warm. Sunny yellow is usually a color reserved for spring and summer, but there are ways to make it work for winter as well.
Divino Lora Midi Dress + Black Crepe Jacket
The Divino Lora Midi Dress is the ideal color and style for all the holiday parties in your winter schedule. From Christmas to New Year’s Eve and into Valentine’s Day, you can’t go wrong with such a bold and sexy red dress. With a version of a corsage style top, front side slit, and stretch crinkle fabric, the dress is a must-wear for any event, especially a winter wedding
Play up the material’s unique texture by wearing it with a black crepe coat for formal affairs or an evening out. Then, to shake things up, add on a sparkly gold stole or scarf for an added punch of glamour. Black t-strap heels or gold heels both complement the interesting details of the dress and can transform it from elegant and sophisticated to flirty and party-ready. Either way, this red hot dress works just as well for the holiday season as it does in the height of summer.
Take stock of the dresses you normally reserve for the summer months and create a whole lineup of outfits as you prepare for the cold weather. With a few key pieces, you can easily decide how to wear resort dresses in winter so you never have to pack your favorites away.
Planning a look for the summer months? Check out our blogs on What is a Slip Dress and What is a Caftan Dress to get inspiration. Explore our style guide to find out what to wear with a slip dress.