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It’s Hot, It’s Cold: What to Wear This Fall

free people cardigan
Free People Cardigan $128

Sure, we’re all excited to wake up to crisp cool air, especially after a series of late-summer heat waves—but fall is a sneaky season. You will regret those early-morning fashion choices when you’re sweating in your, well, sweater.

We’re so eager to wear our new supple sweaters that we can easily forget 60-some degrees is still pretty warm—and does not require knee boots and turtlenecks.

To help with the seasonal transition, here are a few styles from summer and fall that you can mix and match to wear on the coldish/warmish days without looking like a cold/hot mess.fall to wear now

Clockwise from left: Maxi dress (Madewell $40); Oversized cardigan (Zara $70); Toothpick jean (J.Crew $60); Scoop neck top (J.Crew $40); Suede shorts (Alexa Chung for AG at Intermix $748); Ankle socks (J.Crew $6); Clog sandal (No. 6 at Net-a-Porter $275); Bootie (Rag & Bone $525).

Summer styles you can wear for fall:

Sleeveless summer dresses

summer dresses for fall

Clockwise from top left: Perforated dress (J.Crew $120); Embroidered dress (Madewell $100); Maxi dress (Madewell $70); Eyelet dress (Madewell $100); Print Dress (whit® for Madewell $300); Stripe dress (Madewell $70). 

Typically shoulder and arm bearing dresses scream summer—but if you pair this with the booties from fall and a oversized sweater (one you can peel off in the afternoon heat) the look works! Madewell has a huge selection of beachy dresses that are all on sale now if you want to have your last hurrah of the summer season.  

Sandals (This doesn’t mean flip flops…don’t wear flip flops out in the fall. Honestly, wearing rubber flip flops is not acceptable footwear for everyday. Save the flip-flops for the beach…or the nail salon!)

summer shoe in fall

Clockwise from top left: Slide sandal (Robert Clergerie $276); leather crossover slides (Gucci $410); clog sandal (No.6 $265), thong sandal (Acne Studios $390); clog crossover sandal (No.6 $275).

Any shoe that exposes your foot can feel like a summer shoe, BUT you can work these into a fall wardrobe with a few tricks. Throw on a cute thin knit sock (perhaps brightly colored) with a strappy clog or suede sandal. BANG!


Bright colors

jcrew fall 2015
J.Crew Fall 2015

Despite what J.Crew says, wearing whimsical yellows and poppy pinks is generally reserved for summertime. If your closet is overflowing with cotton-candy colors you might as well wear them now before your tan fades then switch to rich jewel tones for late fall.


From left: Neon green sweater (J.Crew $55); linen t-shirt (J.Crew $20); shirt with pockets (Zara $50).


Fall styles you can wear right now are…

Cropped dark denim

Dark Denim

Above from left: Rag & Bone ($245); Current/Elliot ($230); J Brand ($160); Frame Denim ($200); Madewell ($130).

Dark denim is definitely not a summer look (just thinking about tight dark jeans in 90-degree heat makes me want to dump a bucket of ice water over my head!


dark denim neon outfit

BUT how great would a pair of cropped dark rinse toothpick jeans look with sandals and neon right now? You can rock the crop now without worrying about your ankles freezing! Clockwise from left: Toothpick jean (J.Crew $60), Scoop neck top (J.Crew $40), Clogs (No. 6 at Net-a-Porter $275). 




Ankle booties are perfect for transitional weather. They don’t cover your whole leg so you won’t overheat, and they look great with any length outfit, mini, midi or maxi! Light colors work better for early fall—they’re less severe. Clockwise from top left: Grey suede flat boot (Rag & Bone $525); grey suede western bootie (Sole Society $90); tan leather bootie (Rachel Comey $403); grey block heel bootie (Sam Edelman $140); orange bootie (Rachel Comey $403); brown suede moccasin (Madewell Rory $168); brown leather and suede bootie (Madewell Cait $210); taupe suede high heel bootie (Madewell Billie $228); grey metal heel bootie (Zara $120). 

Style advice: Wear your suede booties now, before the first snowfall—because the salty slush will ruin them!


Suede and Leather

Clockwise from top left: Suede shirt (Net-A-Porter $1,345); suede off-shoulder top (Intermix $350), Suede flare pants (Frame Denim $1,050), Perforated leather shell (J.Crew $300), Leather leggings (Balenciaga $1,845), Suede shorts (Intermix $325), Suede pants (Net-A-Perter $1,295), Leather skirt (Zara $190).

Leather and Suede are definitely winter wear BUT if you pick a lightweight suede short or skirt it can work for right now without looking too heavy–even in black.

Style advice: If you’re going to wear full-on suede or leather in fall, stick to light earthy tones or gray. Save the black and dark hues for winter. Shorts and minis are fine in any color.

Remember to have fun with fall fashion because before you know it we’ll see single digit temperatures and you’ll be lost inside your puffer coat wearing multiple base-layers and thermals.

Check out our Fall Fashion board on Pinterest for more transitional style inspiration


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