I Always Turn to This One Outfit Combo When Spring Hits
Sponsor Content Created With Free People
I always have that one outfit combo I tend to gravitate toward for different times of the year: In winter, it's the classic coat, chunky sweater, and jeans trio, and in summer, it's usually long shorts with sandals. But right now we're in that in-between time when it's not quite hot but still too warm for coats, for which there's one pairing that truly never fails: boots with a dress. It's like the two were made for those end-of-winter moments. It means I don't have to worry about paying for a pedicure yet, but I can still show a little skin (or not—don't get me started on my love for a good maxi dress).
If you didn't know Free People was a goldmine for this said go-to, prepare to be nothing short of amazed. The site is bursting with maxis, midis, and minis, and its boots section is like no other. Combat, western, tall, you name it—it has it. To show you what I mean, I put together two (very cute, if I do say so myself) outfits featuring my favorite pieces on the site right now. Keep scrolling for a couple looks I'll be wearing on repeat, plus a few more items that will be added to my rotation very soon.
Shop my looks:
How is it that I feel so dressed up and so casual at the same time? I could totally wear this for date-night drinks outside or just an über-comfortable WFH fit. Plus, these boots will also look good with anything from midi skirts to straight-leg jeans.
I am giving myself major festival vibes in this fit. I might just have to plan a faux-Chella with my quarantine bubble. The red dress is such a fun and easy vibe, but the white boot just pulls it together perfectly. I'll definitely be putting this on for warmer days around my new apartment in Venice while I wait for that trip to the desert.
Shop even more dresses and shoes I'm loving from Free People:
I feel like I see people on Instagram in this dress all the time.
I'll definitely wear this together, but I'm also already plotting an outfit with that top and a pair of straight-leg jeans.

Anneliese Henderson is a Los Angeles–based senior editor on the branded content team at Who What Wear where she covers the latest in fashion, beauty, and lifestyle. When she’s not writing about her favorite trends, you can find her reading a book by the beach or spending money on overpriced smoothies at Erewhon.
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