Style Guide: Transitional Fall Dresses

Style Guide: Transitional Fall Dresses

Can you believe summer's already over? While we're excited for tailgates and cozy sweaters, parting with our favorite summer clothes doesn't feel quite right this year. Instead of packing away those beloved preppy dresses for the winter, why not create a transitional wardrobe that works year-round?

Say goodbye to strict seasonal dressing and embrace these early fall outfit ideas to keep your preppy dresses in rotation throughout the year.

Woman in Coral Geometric Dress

 How to Transition Preppy Dresses from Summer to Fall

The key to transitional dressing is simple: layers. Fall is notorious for having unpredictable weather. One minute it’s warm and sunny; the next, it’s cold and windy. Layering makes it easy to adjust your outfit accordingly throughout the day. While that summery seersucker dress may not be fall-friendly on their own, paired with the right layers, it’s ready for any weather.

Here are some transitional outfit ideas for wearing your preppy Southern Tide dresses this fall. 

1. Layering Magic

The key to transitional dressing is layers. Fall weather can be unpredictable, but layering allows you to adjust your outfit effortlessly. Your summery seersucker dress can become fall-friendly with the right layers.

2. Denim Jacket Companionship

For a perfect tailgate outfit on a breezy fall day, pair your preppy dress with a denim jacket and casual sneakers. It's comfortable, cute, and ready for any weather. Tie the jacket around your waist when the afternoon warms up.

3. Blazer Elegance

Whether you’re back to working in an office or still working from home, a preppy dress and a blazer make the perfect work outfit for fall. For printed pieces— like a floral midi or a striped t-shirt dress— stick to a basic blazer in a neutral shade. If you’re feeling extra preppy, choose a coordinating color or a fashion-forward monochrome look. Pair with office-appropriate ankle boots (or fuzzy slippers if you're at home).

4. Wear a Summer Dress as a Skirt

Turn your favorite preppy, summer dress into a fall-friendly skirt by layering it under a sweater or blouse. This works particularly well with floral prints and midi dresses. To avoid uncomfortable bulk around your arms. Stick to styles that are sleeveless or have fitted short sleeves. Add tights if it’s extra chilly outside.

 5. Cozy up in a Cardigan

 When working from home, you want to feel comfortable while still looking professional. A summer dress and a cozy cardigan make the perfect pair. Try layering a super soft cardigan over a professional shirt dress, or a preppy cardigan over a casual t-shirt dress. Either way, you’ll look professional enough for video calls and while enjoying the comfort of your home (and outfit).

6. Layer Preppy Dresses Over a Turtleneck

 For a classic fall look, layer your preppy dresses over a basic turtleneck. The trick to nailing the look is to choose a turtleneck that’s fitted throughout the body. That way, it won’t bunch up around the waist. This transitional outfit works well with summer styles– like a wrap or tank dress— in more fall-appropriate fabrics like chambray denim.

7. Accessorize Wisely

 Fall accessories are an easy way to add warmth to an end-of-summer outfit. Instead of pairing your summer dresses with open-toe sandals, pair them with ankle or knee-high boots instead.

Woman in green, quilted fall dress.

Thanks to these helpful tips on how to wear dresses in cold weather, you can keep your favorite summer pieces in your closet, even as the temperatures begin to drop. Check out our women's new arrivals for more transitional outfit inspiration.



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