Sundresses

Flaunt Your Style In Fall & Winter Sundresses

As the air turns crisp, don’t tuck away your favorite sundresses just yet. Windsor’s versatile sundress collection lets you transition effortlessly into the cooler months while keeping your style fresh and seasonal. These dresses, known for their light and breezy feel, transform into perfect fall sundresses when paired with cozy layers like cardigans, denim jackets, and boots. Whether you’re headed to a weekend brunch or dreaming of a winter getaway, these flowy dresses will have you looking chic all year round.

Imagine walking through a crisp fall day, wrapped in a beautiful sundress with darker tones like olive or burgundy, layered under a soft sweater-knit cardigan. Sundresses in these rich hues, especially dark floral dresses, bring a fall-appropriate vibe to your wardrobe. And when cooler days arrive, sundresses in heavier fabrics like cotton knits, velvet, and crochet allow you to embrace the season without sacrificing comfort or style. Embrace these colors and fabrics on new print dresses with marble patterns or soft watercolor prints.

Feeling unsure about styling a sundress for the winter chill? It’s easier than you think. Layering with jackets and boots, or even adding warm tights, keeps you cozy while maintaining the breezy essence of the sundress. Pair with long sleeve tops or tie-front blouses also updated at Windsor so you can create your perfect cozy, layered look. Plus, with Windsor’s collection of beach dresses, you can pack for those tropical winter escapes in style. Explore the viral trend of milkmaid dresses for more sundress outfit ideas.

Looking for the perfect outfit for a bridal shower or a casual daytime event? Our sun dresses can be styled for any occasion. A cozy scarf or tights, paired with sleek boots, turns your sundress into the ultimate blend of fashion and function. Whether you’re gravitating towards a mini sundress or a long, flowing silhouette, there’s no shortage of ways to make your look stand out.

Shop Windsor’s range of fall sundresses and discover how easy it is to carry your favorite styles into the colder months. From bridal showers to casual get-togethers, our collection offers something for every event. Visit us in-store at over 350 retail locations or shop online to find the perfect year-round look!

What is a sundress?

A sundress is a casual dress style that is intended to be worn during warmer weather. This informal dress style typically features wider necklines, sleeveless bodices, and/or narrow shoulder straps or dainty sleeves. You can also find some smocked or halter dresses that offer a sleeveless sundress design. Beach dresses and summer dresses are considered similar styles and all can be found at Windsor in mini, midi, and maxi lengths. Sundresses in these varying lengths are perfect for different summer festivities, such as picnics, brunches, baby showers, bridal showers, birthday parties, or wedding-related events. Sundresses are known for being composed of lightweight fabrics like cotton to combat the heat. For the fit of this casual dress style, the design typically offers a flowy, loose fit that doesn't adhere close to the body. Sundresses are a closet staple during warm weather months and offer a feminine look to any casual outfit.

How do you wear a sundress to work?

You can style up a sundress to wear to work with some key staple pieces. Dress it up with chic layers and pretty accessories. Layer on a lightweight cardigan or duster, a structured blazer, a denim jacket, or a sleek moto-style jacket to add coverage to the sundress. Pair the look with strappy mules, classic block heels, trendy wedges, or your favorite ankle booties. Silver or gold hoop earrings are a perfect addition, as well as dainty chain-link necklaces or freshwater pearl stud earrings. Level up your sundresses with belts to cinch your waist and create a flattering silhouette. Sundresses are an effortless style you can style up to impress at the office!

How can I style a sundress for a party or date night?

You can style your sundress for date night or a party by dressing it up with statement accessories and/or creating layers. A sundress is a casual style, so start by shopping for minimal prints and solid colors that style up this laid-back design. If you're looking to wear it for a dressy event, you'll want statement pieces that enhance your look from head to toe and don't clash with your dress. Choose statement necklaces that feature chunky chain link designs, layered charms, and/or gemstone accents. You can also dress up your sundress with statement earrings like textured door knockers, oversized hoops, and rhinestone studs. For footwear, you can dress up with the latest ladies' shoe styles in mules, wedges, and block heels. Choose a stiletto heel to bring the sexy for a fitted dress style. If your date is taking place at night or on a cooler day, you can layer up with a moto jacket, long-sleeve duster, or a cropped denim jacket to complete your outfit. To add texture or colors, you can also play with tie-front tops, fashion kimonos, and trendy lightweight jackets that compliment your shoes, purses, or belts.