Styling a Summer Maxi Dress for Fall

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November 2, 2021

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We all love some good fall fashion, but as someone who lives for warm weather, bundling up is something I dread. It’s a necessary evil in order to stay warm during those unfortunate days I’m not on an island basking in the sun (lol!). Since I love tropical weather so much, I invest a lot of my wardrobe budget into resort wear. Even when it’s winter here, I find the time to travel and therefore can justify those purchases since I technically wear maxi dresses and swimsuits year-round.

After spending some time window shopping for fall clothes online, I decided instead to try and repurpose some of my coveted resort wear pieces for fall. I did something similar last year, but this year, I finally decided to pull the trigger on a solid pair of combat boots, which served as the primary piece for this look.

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I browsed through my closet for a summer maxi dress with some fall colors. This black and tan striped white dress (which also comes in black with tan stripes!) was perfect, despite it looking so summery when I wore it in Turks & Caicos! Then I added a sweater that highlighted the tan color of the dress and topped it off with a black suede moto jacket. I felt feminine, but also a little badass. I definitely felt like the slits on the side helped me avoid looking like a housewife from the horse and buggy days, and I was totally warm enough for the lower temps we had this past week.

I had a lot of fun styling this summer maxi dress for fall, so it will definitely be a goal of mine to re-wear clothes throughout the seasons a bit more. I am also over the moon about these gorgeous, feminine combat boots. The gold buckles add the perfect touch of softness, while still maintaining that cool-girl feel.

How do you wear your summer clothes into fall?

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Photos by Ryan Carpenter.