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What to Wear When It's Almost Fall (Still Warm)

Purple Star emoji 16 items
The transitional edit for that warm-but-you-want-fall stretch: dresses you can wear bare now and layer over tights later, real cashmere under $160, and the relaxed denim that ties it all together. Everything under $300, pulled from three of the best ...
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Transitional Dresses

The transitional dresses edit I'd text a friend — no styling degree required.

 
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A navy plaid dress is the fastest way to signal fall is coming without giving up on bare arms just yet. Wear it now on its own, then add a leather jacket and boots when the mornings turn.
Sorra Dress in Navy Saige Plaid
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Brown-and-cream polka dots feel distinctly autumnal — warmer than a summer floral, softer than black. It moves beautifully, so it's the one you'll reach for when you want to look done with zero…
Mabel Maxi Dress in Brown & Cream Polka Dot
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A black tank maxi is the workhorse of a warm-fall wardrobe: bare and easy while it's hot, then instantly cool-weather with a chunky cardigan thrown over and a boot underneath.
Valley Racer Tank Maxi Dress in Black
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The kind of long black dress that quietly does the most — dinner, a gallery opening, a wedding where you weren't sure of the dress code. Add a blazer and it reads pulled-together for cooler nights.
Lacelle Maxi Dress in Black
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Ivory and black is the combination that always looks more expensive than it is. Keep it leggy while the weather holds, then throw it over tights and knee boots the second it drops.
Blake Mini Dress in Ivory & Black
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Proof a great black maxi doesn't have to cost a fortune. It's the throw-on-and-go piece for that in-between stretch — sandals now, ankle boots and a denim jacket in a few weeks.
Thea Maxi Dress in Black
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The Cashmere Edit

The the cashmere edit edit I'd text a friend — no styling degree required.

 
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Real cashmere for the price of a nice acrylic pullover is a genuinely rare find. This is the crewneck you'll pull on over everything — jeans, a slip skirt, straight over bare skin when the AC is…
By Anthropologie Goldie 100% Cashmere Sweater
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A mock neck is the sweet spot between a crew and a turtleneck — warm at the throat without the fuss. In cashmere it's the piece that makes leggings-and-boots look intentional.
Pilcro Alani 100% Cashmere Mock Neck Sweater
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A sleeveless cashmere tank is the smartest transitional buy there is: cool enough for a warm afternoon, luxe enough to layer under a blazer when the office runs cold. It goes with literally…
Pilcro Jensen 100% Cashmere Muscle Sweater Tank
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The one piece that turns jeans and a tee into an outfit. A cashmere poncho vest is that easy layer you throw on at the door — cozy, a little dramatic, and it packs down to nothing for travel.
By Anthropologie Enza 100% Cashmere Poncho Sweater Vest
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A little puff at the sleeve is the detail that makes a plain sweater feel considered. The cotton-cashmere blend means you can wear it before it's truly cold without overheating.
By Anthropologie Cotton Cashmere Puff-Sleeve Sweater
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Denim To Live In

A few denim to live in worth your tap — throw-on-and-go, every time.

 
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Roomy, low-slung, and that soft washed blue that looks lived-in from day one. These are the jeans you'll wear with the cashmere and boots on repeat once the temperature actually cooperates.
Motel low slung roomy jeans in breeze blue
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Off-white denim keeps the summer feeling going a little longer and looks unexpectedly chic against fall's browns and camels. Straight, parallel leg — the flattering, goes-with-anything cut.
Motel low rise parallel jeans in off white
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A darker, dustier vintage wash that reads a touch more grown-up than a bright blue. Slouchy through the leg so they balance out all those fitted knits you're about to be living in.
Motel low slung roomy jeans in vintage blue
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The barrel leg is the shape everyone's reaching for, and under $55 it's a low-risk way to try it. Dark rinse makes it the dressier pair — tuck in a knit and add a heeled boot.
ASOS DESIGN slim barrel jeans in dark blue
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A brighter, used-look wash for the days you want your denim to be the whole point. Parallel leg keeps it clean and easy — pair with a cropped cashmere and you're out the door.
Motel low rise parallel jeans in bright blue used
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