How to Wear a Summer Dress Into Fall

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Now that fall has officially arrived in the south, I’ve been left scrambling for warm clothes and cute fall outfits due to my fall and winter clothes being locked away in storage. Since I haven’t had a chance to go grab them yet, I’ve had to get creative. I have a couple light jackets here that I kept out of storage since I’m always cold and I did order one new pair of boots that are absolutely amazing, so I’ve been using them to warm up my summer outfits.

The key to wearing a summer dress into fall, especially this time of year, is layers. Lately it’s been freezing in the morning, cool around lunch, sweltering in the afternoon, warm in the evening, and then freezing again at night. So I’ve been pairing my OTK books with shorts and a tee, jeans, and summer dresses. And then to stay warm during those cold hours of the day, I’ll add on however many layers I need.

On this particular day, I wore this look out for dinner. So I didn’t really need the jacket at first, but then definitely had to wear it once the sun was gone. As it gets even colder, I’ll add a sweater and then the jacket on top of that. Contrary to hat yyou might think, the over the knee boots do an amazing job of keeping you warm. They’re thick enough to almost act as pants and keep your toes nice and toasty. I think I need them in every color actually.

How to Wear a Summer Dress Into Fall, free people maxi dress, fall outfit ideas, summer dress in the fall, otk boots, over the knee boots, fall style, what to wear for fall, bb dakota jacket, goodnight macaroon over the knee boots styled

How to Wear a Summer Dress Into Fall, free people maxi dress, fall outfit ideas, summer dress in the fall, otk boots, over the knee boots, fall style, what to wear for fall, bb dakota jacket, goodnight macaroon over the knee boots styled

How to Wear a Summer Dress Into Fall, free people maxi dress, fall outfit ideas, summer dress in the fall, otk boots, over the knee boots, fall style, what to wear for fall, bb dakota jacket, goodnight macaroon over the knee boots styled

How to Wear a Summer Dress Into Fall, free people maxi dress, fall outfit ideas, summer dress in the fall, otk boots, over the knee boots, fall style, what to wear for fall, bb dakota jacket, goodnight macaroon over the knee boots styled

How to Wear a Summer Dress Into Fall, free people maxi dress, fall outfit ideas, summer dress in the fall, otk boots, over the knee boots, fall style, what to wear for fall, bb dakota jacket, goodnight macaroon over the knee boots styled

How to Wear a Summer Dress Into Fall, free people maxi dress, fall outfit ideas, summer dress in the fall, otk boots, over the knee boots, fall style, what to wear for fall, bb dakota jacket, goodnight macaroon over the knee boots styled

 


 
I really love how this look turned out. It just hit me one day that I wanted to try my otks with a maxi and now it’s totally my new favorite summer to fall look. I have a few more dresses I’ll definitely be doing this with and I can’t wait to share!

What’s your favorite way to wear your summer clothes into fall?

Photos by Ryan Carpenter.