16 Cute Outfits to Consider Wearing and Shopping This Fall


Before we know it, summer’s blazing heat will swiftly transform into a cool breeze, and cute outfits for fall will become top of mind. This season’s looks are arguably the best, especially since the transitional weather gives us an opportunity to play with unexpected layers and rich, textured fabrics.

Once the temperature drops, there’s no need to completely forget about your summer faves; follow the latest wave of street style stars and pair those crop tops with leather trousers and style those mini skirts with longline blazers. You could even savor a few more days with your sandals if you wear them with a great pair of jeans or a crocheted knit top.

Find out exactly how to put together a few cute outfits for fall below. Plus, get a head start on shopping for transitional pieces too.

Photographed by Acielle / StyleDuMonde

The Easy Evening Look

Yes, it’s possible to get dressed up and stay cozy, especially when your outfit combines soft, plush knits—like a Jacquemus cardigan and a stretchy midiskirt.

Jacquemus Azlou cropped mohair-blend cardigan

& Other Stories mismatch gem pendant earrings

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Prada logo pointed-toe mule

Photographed by Acielle / StyleDuMonde

The Chic Errand Runner

Get the most out of those summer shorts on warmer fall days by pairing them with snuggly sweaters. You’ll get bonus points if you pick a cheerful color like this sprightly yellow combo.

Polo Ralph Lauren wool-blend sweater

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Staud Sorno fringed tweed shorts

$225$112

MATCHESFASHION.COM

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By Far Manu patent shoulder bag

AZ Factory collapsible-heel sneakers

Photographed by Acielle / StyleDuMonde

The Back-to-School Vibe

Stay ahead of the class in a chic argyle vest and on-trend wide-leg trousers. There’s no need to overthink it, so have fun mixing colors.

Burberry Mackenzie sleeveless argyle sweater

Galvan Lido high-rise wide-leg satin pants

Dr. Martens Jadon Pisa platform boot

Photographed by Acielle / StyleDuMonde

The Canadian Tuxedo

Double up on denim with a structured jacket and coordinating jeans, which are easily elevated with a pair of mules and a designer handbag.

Everlane The Denim Chore jacket

Everlane The ’90s Cheeky straight jean

Balenciaga hourglass croc-embossed leather keychain card case

Prada 45mm triangle logo slingback pumps

Photographed by Acielle / StyleDuMonde

The Back-on-the-Town Knockout

Return to nightlife with a cool leather blazer and playful plaid skirt just like the ones from Frankie Shop and Maje below.

Frankie Shop Olympia faux leahter blazer

Maje Joris plaid pleated cotton skirt

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Gucci 2015 re-edition sandal

Photographed by Acielle / StyleDuMonde

The Detailed Minimalist

Tried-and-true neutrals will never fail you, especially tailored separates similar to the vest and flowy trousers here.

Goldsign open-back halterneck vest

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Aje Universal wide-leg hemp trousers

Khaite The Adeline crossbody bag

Le Specs Air Heart sunglasses

Photographed by Dan Roberts

The Back-to-the-Office Hero

No need to force your feet into heels. A classic pair of New Balance sneakers will look just as chic with your blazers and trousers.

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Alex Mill Mathilde linen and cotton-blend vest

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Zara slit ribbed leggings

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New Balance Made in US 990 V5 sneakers

Photographed by Acielle / Style Du Monde

The Weekend Winner

Florals for fall? Absolutely. Just look for cozy knits, like this one from The Series. It pairs well with jeans and skirts.

Ksubi Playback high-rise straight-leg jeans

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Loewe Flamenco nano chain strap leather crossbody bag

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Photographed by Acielle / Style Du Monde

The Elevated Casual Look

Never underestimate the power of a tan blazer. It will upgrade all your T-shirts, jeans, and sneakers.

Tu Es Mon Tresor Emerald high-rise striaght-leg jeans

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Adidas Stan Smith leather sneakers

Photographed by Acielle / Style Du Monde

The Polished Combo

If you don’t already own a sweater vest, you might want to get one. The preppy trend is showing no signs of slowing down. Plus, it looks great over a T-shirt, button-up blouse, or turtleneck.

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Plan C sleeveless stripe wool-knit top

$650$195

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Weekend by Max Mara Sovrana trousers

Photographed by Acielle / Style Du Monde

The Glitz and Glam

Not every special event requires a dress. A pair of leather trousers will go a long way this fall. And they certainly command attention, especially when combined with a bright blouse.

Marco De Vincenzo bow blouse

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Nanushka Namas wide-leg vegan leather pants

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Acne Studios Musubi mini knotted leather shoulder bag

& Other Stories thong strap heeled leather sandals

Photographed by Acielle / Style Du Monde

The Twisted Prep

Give polished blazers and skirts a cool upgrade with trendy bucket hats and platform sneakers.

LVIR wool-blend twill blazer

Converse Run Star Hike sneakers

Photographed by Acielle / Style Du Monde

The Refined Sportswear

Baseball caps might be the unexpected accessory hero come fall. We’ve seen celebs wearing them with going-out dresses, but you can also sport them with a sweater vest (yes, there’s another one) and jeans.

Ganni sleeveless checkerboard knit sweater

Levi’s 505 high-waist straight-leg jeans

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Balenciaga embroidered cotton twill baseball cap

Neous Sika toe-ring leather sandals

Photographed by Dan Roberts

The Reveal and Conceal

Show off a little bit of skin with a barely-there bralette underneath an oversized, boxy blazer.

H&M oversized linen-blend jacket

Jacquemus Valensole ribbed bralette

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Rag & Bone studio pintuck jersey trousers

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Photographed by Dan Roberts

The Pops of Color

Just because the days are a little darker doesn’t mean you have to dull down your wardrobe. Have fun mixing shades, like red, yellow, and green.

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Alice + Olivia Camara rolled-crewneck cropped tank

Deadwood Presley leather wide-leg pants

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Bottega Veneta BV fold crossbody bag

Bottega Veneta stretch leather-trimmed mesh pumps

Photographed by Dan Roberts

The Surfer in the City

Nope, the fashion crowd isn’t over the effortless vibes of tie-dye just yet. So pair that colorful tee with white jeans and a coordinating bag this fall.

Gabriela Hearst Miller tie-dyed cashmere sweater

AGoldE balloon high-rise tapered jeans

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Bao Bao Issey Miyake Lucent matte geo shoulder bag

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