30 Cozy-Chic Looks To Inspire Your Fall Dressing

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Just like that, spooky season is over. (That is, unless you’re counting Election Day, which would leave you with 24 hours — or four more years — of horror.) It’s time to pack away the skeletons and Madonna costumes (we see you, JLo, and we salute you) and get to thinking about your fall wardrobe. Transitional weather is gone for good, and with it, your time to dillydally about swapping out your seasonal favorites and replacing the pieces that need a refresh. Perhaps your usual wool coat has more pilling than can be saved by an annual trip to the dry cleaners, or maybe your favorite high-heeled, thigh-high black boots aren’t made with a pandemic in mind. Either way, you’ll likely need a little inspiration in the fashion department before any true work can be done.

To counteract any what-to-wear-induced fatigue, we’re letting you in on a little secret: the answer to autumnal dressing is all over Instagram. On the app, you’ll find everything from fall shoe trends that everyone must own (hint: loafers, riding boots, and dad sneakers) to layering hacks, all of which will make getting dressed this season — whether you have anywhere to go or not — easier than ever before. And to ease the selection process even further, we went ahead and rounded up an outfit for every day of the month in the 30 fall-fashion-filled slides ahead.

This is fall layering at its very finest.
Check out this fall-ready ensemble, featuring a banana yellow knit and the only sneakers you need to buy this season.
Big boots and layered on knitwear? If you ask us, there’s no better sartorial combo for fall.
Inside or out, you can never go wrong with a ribbed sweater dress.
More vests and knee-high moto boots, please!
Catch us matching our knitwear to our outerwear for the remainder of the cold weather.
For those days when you need a jacket, but you’re not quite ready for closed-toe shoes.
BBE: Big Boot Energy.
Your fall color scheme doesn’t have to match the dreary weather.
We’re keeping the bras-as-tops trend going for as long as the weather will allow it.
All hail the power of clashing prints!
Always — and we mean always — add a shoulder sweater.
Leather pants: check! Telfar bag: check! Cloud knit: check! This look is truly checking off every single one of our fall boxes.
Seven fall-friendly outfits, all in one post. You’re welcome.
The only way to wear hiking boots when not on an actual hike.
Is it just us or are leggings getting more and more appealing by the day?
This mod-patterned onesie is a ’70s vibe.
Mixed quilts and dad sneakers will always win out in our book.
Hope for denim is not lost after all, as proven by this jeantastic look.
Between the color palette and the textures, this look is everything we needed to see today and more.
Strong shoulders are a must for fall.
Clashing plaid and knee-high boots will forever be a fall mood.
Every fall wardrobe needs a school-girl-inspired pleated mini skirt.
Nothing beats a coat so long and cozy that you could wear essentially anything underneath and no one would notice.
It’s all about stirrup leggings for autumn.
Schoolboy knits and frilly dresses somehow manage to be the perfect fall pairing.
It’s the corset for us.
Throw on a leather trench if/when the weather permits.
This look is a lesson in wearing your Nap Dresses (and house dresses in general) all year long.
With the right trench coat, even a wedding dress can look autumnal enough for everyday wear in November.

Like what you see? How about some more R29 goodness, right here?

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