Transitional Fall Outfit Ideas for Preppy Dresses

Can you believe summer’s already over? While we can’t wait for the tailgates and cozy sweaters that come with fall, we aren’t quite ready to say goodbye to our favorite summer clothes. This year—after admittedly wearing stretch pants for most of the summer— it doesn’t feel quite right to put our favorite preppy dresses away for the winter.

While your mother may have separated her closet into two distinct summer and winter wardrobes, you certainly don’t have to. In fact, more women are choosing to ditch seasonal dressing in favor of one transitional wardrobe that works in any weather. Before your annual summer-winter closet change, check out these transitional fall outfit ideas to learn how you can keep your favorite preppy dresses in rotation year round.

women in preppy dress with stripes and a jean jacket

 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. Add a Pair of Tights

Adding a pair of tights can take your dress from summer to fall in a snap. Balance out lightweight fabrics with a pair of sheer tights, and save your opaque tights for t-shirt dresses and heavier fabrics. Style with ankle boots or knee-high boots to make your dress feel even more fall-appropriate. Unless you’re feeling adventurous, it’s best to stick with basic black.

2. Throw on a Denim Jacket

What’s our perfect tailgate outfit for a breezy fall day? A preppy dress in a team color, a denim jacket, and a pair of casual sneakers. It’s comfortable enough for an all-day tailgate, cute enough to post on the ‘Gram, and ready for any weather! 

During your morning tailgate, wear the denim jacket over your dress with a sporty scarf that shows your team pride. If the weather warms up in the afternoon, you can tie your denim jacket around your waist while you cheer on your team.

gameday tailgating dress

3. Add a Blazer

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).

4. Wear a Summer Dress as a Skirt

Turn your favorite summer frock 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 feel comfy enough to answer emails from the couch.

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. Keep your feet warm inside by slipping on a pair of fuzzy socks. Top off casual looks with a beanie or wrap up in a cozy blanket scarf.

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.