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People love fall for the fashion, but I always struggle to put together trendy and cozy outfits. I like to keep things simple, so my go-to combo of the season has been a cute fall dress teamed with boots. This easy pairing helps me speed out the door in record time and garners so many compliments — yet doesn’t take much time to assemble at all.
The key is to choose a comfortable dress (preferably a flowy or soft one) then wear it with whatever boots you have on hand. Most dresses can be paired with a variety of footwear and accessories, so you can get many wears out of just a few pieces. Are you ready to upgrade (and seriously streamline) your fall wardrobe? I compiled the most comfortable and versatile fall dresses which will quickly become staple pieces in your autumnal closet for years to come.
1. Swiss Dot Perfection: Any sort of babydoll dress will look fun and casual with knee-high boots. This one with Swiss dot overlay comes in 11 deep hues that are perfect for fall. Pair it with a leather jacket and a wide-brimmed hat and you’ll be the most stylish person in town — just $46!
2. The Comfiest of All: Many popular sweater dresses are big and bulky. This one from Weeso reminds Us of our favorite long-sleeve T-shirt. Plus, it has pockets — was $38, now just $19!
3. Perfect for Dinner Dates: We love wearing dresses during big meals (no uncomfortable constriction here!). The elastic empire waist on this BTFBM dress enhances the comfort factor. A pair of tan boots will mesh well with whatever color you choose — was $36, now just $31!
4. Made for Thigh Highs: There are so many ways to style this simplistic tunic dress, but it really looks incredible when worn with thigh high suede boots — was $41, now just $36!
Us Weekly has affiliate partnerships so we may receive compensation for some links to products and services. An hourglass figure is gorgeous — but properly accentuating it and finding flattering clothing can be a bit messy. The wrong type of shirt or dress, for example, can lead to a boxy look, leaving your waist lost […]
5. Tied With a Bow: You really can’t go wrong with a wrap dress. This ruffled style from Naggoo is one of the most comfortable (and stylish!) options on the internet — just $36!
6. Break out the Booties: Not in the mood to wear tall boots? This Kinmiu swing shift dress looks impeccable with booties — just $38!
7. The Button-Down: Button-down dresses that resemble oversized dress shirts are all the rage right now. Instead of looking like we raided our dad’s closet, though, we love this belted corduroy style in green. Just imagine wearing it with a pair of chocolate boots. Perfection — was $41, now just $33!
8. Fall Florals: Another great pick from BTFBM, this flirty dress prove florals aren’t just for spring — just $43!
9. Cold Shoulders: We love that this swingy dress feels like the most comfortable pair of pajamas, and the off the shoulder look is super trendy — was $46, now just $37!
10. Solid Shirt Dress: The patchwork detailing and cowl neck on this supremely soft shirt dress sets it apart from other designs we’ve seen. We’re especially fond of the attention-grabbing leopard colorway – was $51, now just $33!
11. A Longer Option: Short dresses and cold weather obviously aren’t a match made in heaven. If you’re looking for something a bit more modest, this knee-length stretchy beaut is one of our favorites. And it still looks gorgeous with a pair of tall boots — was $36, now just $30!
12. Plaid Perfection: If only it was acceptable to wear a blanket everywhere… Well, this flannel dress from Mirol is the closest thing to a plush blanket, so you can catch us sporting it all autumn long — was $60, now just $30!
13. Comfy-Cozy: Can you ever have too many sweater dresses? The answer is no. We’re adding this trendy one to our cart ASAP — just $29!
14. Make a Statement: Sure, dark hues may be synonymous with fall, but that doesn’t mean you have to wear them. If you’re looking for something a bit bolder to match your personality, the bright pattern on this Soly Hux dress is sure to please. Cowboy boots also happen to be the perfect pairing — just $32!
15. Blank Canvas: Plain shirt dresses aren’t boring! We consider them a blank canvas which can easily be dressed up with jewelry, jackets and boots. So go ahead, add this staple from Keedone to your wardrobe. You won’t regret it — was $40, now just $26!
16. Another Closet Staple: You can’t go wrong with a bodycon sweater dress. Not only are they comfy cozy, but they look super sleek too — was $54, now just $26!
17. A Fantastic Flannel: Just like your favorite flannel shirt, in dress form. We might just have to pick up one in every color with the affordable price — was $41, now just $39!
18. A Lil’ Bit of Velvet: Yep, you can definitely wear boots with a velvet dress. Just imagine how festive this velvet Naggoo stunner will look with white booties — just $46!
19. Babydoll Dresses Forever: Everyone looks amazing in babydoll dresses, so go ahead and add this one from La Suiveur to your closet — just $36!
20. Mustard Mania: The most underrated fall color? Mustard. This cozy V-neck sweater dress in mustard is begging to be worn before winter sets in — just $40!
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