Summer to Fall Transition Dress Under $20

We’re nearing the end of August and have record temperatures this week in Chicago in the high 90s. And, as much as I love fall fashion, sweater season, boots, and everything cozy, with the heatwave we’ve been having, I think we will have at least another month or two of warm weather. So, I’m sharing how to style a summer-to-fall transition dress to wear now and later.

Dressing for in-between seasons can be challenging. Especially on those days when the temperature starts cool, heats up, and then drops again at night. Adding layers is the simplest way to extend the life of your summer clothing, but I have a few styling tips too. These will help you maximize your summer wardrobe and make it easy to transition between seasons.

Nothing says fall more than plaid, and I thought this red and burgundy plaid dress from Walmart would be fun to style to wear now and later. It’s versatile enough to dress up for a business casual work environment or down for a stroll through the farmer’s market on the weekend. Oh, and it’s under $20 and also comes in a blue plaid, gold, and olive green.

Wear it Now

Wearing darker hues is a simple way to style this summer to fall transition dress when the weather is still hot. For this outfit, I incorporated hints of black with my wedge sandals and the band around my straw hat. To complete the look, opt for a black, brown, or red handbag (read my fall handbag trend post here).

Wear it Later

Suede is a luxe and cozy fabric that instantly adds a warm richness to an outfit. I transitioned this dress from summer to fall by swapping out my sandals for suede booties and adding a suede moto jacket as a completer piece. Grab a felt hat to round out the look. Hats are a fun accessory that will elevate your style year-round.

Another way to transition this dress from summer to fall is to change up your footwear with lug sole loafers, Chelsea boots, or tall boots and add a denim jacket or cropped cardigan as a topper. For the office, try a nude pump and blazer.

Thank you for reading Summer to Fall Transition Dress!

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Also see:

Black Lace Shorts | Fall Transition Outfit and How to Wear Your Summer Dress in Fall

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