The leaves are starting to change from vivid greens to warm reds, oranges, and yellows; autumn-inspired drinks (yes, we’re talking about the PSL) are back; and temperatures are dropping into the mid-to-low 60s in many states. And that can mean only one thing: Fall is fast approaching, so now is the time to prepare and transition your wardrobes for the changing season (and weather).
Not sure where to start? We're here to help! Here is a guide on how to transition many of your summer staples into autumn, and here, the best boot styles to buy, depending on where you live. Today, we're highlighting the cutest, most practical outfits to wear on a rainy fall day, and those who attended New York Fashion Week know firsthand that certain pieces and fabrics don't mix well with rain.
A rainy fall outfit is almost the same as a rainy summer outfit—just add some extra layers to help combat the cooler temperatures. In both seasonal situations, a raincoat is a must-have, good boots are another, and a trendy umbrella is a necessary accessory you didn't know you needed—until now. Ahead, see our roundup of easy fall rainy outfits that are as fashion-forward as they are, er, water-resistant? Then, shop some of our must-haves to help you combat an autumn downpour in style.
A good pair of leather boots is stylish and practical on a rainy fall day.
We can't resist a leopard-print slip dress. Throw a water-resistant trench overtop for a chic yet functional fall outfit.
Because a clear umbrella goes with everything in your wardrobe.
Rainy day fashion doesn't have to be boring, and this red trench is proof.
If you don't yet own a pair of track pants, you're missing out.
Have fun with your trench coat.
A leather jacket is another rainy day essential.
We're certainly not opposed to a pair of metallic boots.
For a warm, rainy fall day, slip into a pair of bike shorts.
Make the trench coat the hero piece in your rainy day outfit.
A gingham coat will always look chic when paired with white pants.
Yes, we're mad for plaid. Join us?
Pair this oversize trench with a chic white slip dress (as seen above).
For those windy, rainy fall days.
Next up, more fall outfit inspiration, right this way,
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Looking Stylish This Fall Means Wearing Your Pretty Dresses With This Unexpected ItemHere's how to master the look.
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Anyone Can Wear a Cardigan, But Only Fashion People Wear Them Like *This*Take note.
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5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This FallTake notes.
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This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025Easy and stylish.
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Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFWLet's dive in, shall we?
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Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to HerA glimpse into the life of this savvy entrepreneur.
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This Simple Fashion Person–Approved Layering Technique Changed the Way I Wear My BasicsEffortlessly cool.
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I Predict These Classic Boots Spotted on London Fashion People Will Dominate NYC Sidewalks This FallAs seen on Daisy Edgar-Jones.
