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1
This bermuda shorts and tank combo
Risk Twenty Two Bermuda Shorts Denim
1
This bermuda shorts and tank combo
Risk Twenty Two Bermuda Shorts Denim
A muscle tank with statement shoulders paired with bermudas is great for those fall days when it's still a tad warm. If it gets chilly at night, simply throw on a leather jacket.
2
this orange look
Cotton Citizen Milan Biker Short
2
this orange look
Cotton Citizen Milan Biker Short
Credit: CourtesyI have a feeling sweats will be a part of my wardrobe for a while, so very into this creamsicle-colored sweatshirt and tie-dye bike short 'fit.
3
this graphic tee and cardigan look
Maje Cashmere Cardigan
3
this graphic tee and cardigan look
Maje Cashmere Cardigan
Credit: CourtesyWant to dress up your fave graphic tee? Turn to a cute pair of leather shorts and a cream cardigan for an easy and cute ensemble.
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4
this denim on denim look
James Perse Slub Cotton-Jersey Top
4
this denim on denim look
James Perse Slub Cotton-Jersey Top
Now 30% Off
Credit: CourtesyDenim on denim will never go out of style. So when all else fails, you can always rely on a good jean jacket, but you can break up the blue tones with a burnt-orange top and accessories.
5
This baby doll dress and boots look
Storets Esther Puff Sleeve Tiered Dress
5
This baby doll dress and boots look
Storets Esther Puff Sleeve Tiered Dress
Credit: CourtesyThis mini dress is the perfect way to transition from summer to fall. Wear it with contrasting combat boots for an edgy vibe.
6
A green on green look
The Range Racer Stretch Cotton-Jersey Tank
6
A green on green look
The Range Racer Stretch Cotton-Jersey Tank
Now 70% Off
Credit: CourtesyThis might just be your new fave color for fall. And major points for a monochromatic look featuring an olive-colored tank, updated cargo pants, and strappy sandals.
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7
Paperbag jeans and a tank
Eloquii High Waisted Jean with Ankle Cinch
7
Paperbag jeans and a tank
Eloquii High Waisted Jean with Ankle Cinch
Credit: Courtesy of EloquiiOpt for a paperbag jean when you want something that feels different than your regular ones; plus, you can always rely on a good ol' black tank top.
8
Cargo pants and a crop top
Daily Paper Cargo Pants Beige
8
Cargo pants and a crop top
Daily Paper Cargo Pants Beige
Credit: Courtesy of Daily PaperNot ready to make the switch from shorts to jeans just yet? I feel you. Try a pair of cargo pants and pair them with a simple cropped tee while it's still warm enough.
9
A waffle sweater and pleated pant look
The Range Waffle-knit cotton-blend top
9
A waffle sweater and pleated pant look
The Range Waffle-knit cotton-blend top
Now 40% Off
If you're ready to upgrade your plain blue jeans, try a bold pleated cuffed pair with a cozy waffle top.
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10
A fancy pajama set
Sleeper Black Tie Feather-Trimmed Crepe de Chine Pajama Set
10
A fancy pajama set
Sleeper Black Tie Feather-Trimmed Crepe de Chine Pajama Set
Credit: Courtesy of Net-a-porterWe've been wearing pajamas for quite some time now, so we might as well wear them out of the bedroom—especially when they're this chic.
11
An elevated sweatpants look
Topshop Gray Slouch Slouch Wide Leg Sweatpants
11
An elevated sweatpants look
Topshop Gray Slouch Slouch Wide Leg Sweatpants
Credit: Courtesy of TopshopI want to wear my sweats 24/7 too. And this outfit is proof that they're more than just loungewear—see how cute they look with a crop top and blazer?
12
A cute jumpsuit
retrofete Tori Jumpsuit
12
A cute jumpsuit
retrofete Tori Jumpsuit
Now 20% Off
Credit: CourtesyThe best part about a jumpsuit is that it's a one and done, pair it with a gold hoop and you're good to go.
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13
A marigold matching top and skirt
WAYF Kati Cropped Tie-Back Top & Jaden Bias Midi Skirt
13
A marigold matching top and skirt
WAYF Kati Cropped Tie-Back Top & Jaden Bias Midi Skirt
Now 64% Off
Credit: Courtesy of Bloomingdale'sYou'll be seeing a LOT of this gorge color come fall. Whether you want to wear this skirt with the matching top or a neutral tee, you'll be right on trend.
14
A graphic sweater and wide leg pants
Topshop Ecru Stitch Wide Leg Pants
14
A graphic sweater and wide leg pants
Topshop Ecru Stitch Wide Leg Pants
Now 50% Off
Credit: Courtesy of TopshopWide-leg pants will never not be in, so I think you def need these! The cream hue will actually go with so much more than you think, like this fun color-block sweater.
15
A beige belted jumpsuit
Ba&sh Clothilde Jumpsuit
15
A beige belted jumpsuit
Ba&sh Clothilde Jumpsuit
Now 30% Off
Credit: Courtesy of ShopbopYou'll be the chicest one around in this beige jumpsuit. Add a belt and pointy-toe booties for a pulled-together look.
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16
A polka-dot dress and sneakers
ASOS DESIGN Ruched Waist Mini Dress
16
A polka-dot dress and sneakers
ASOS DESIGN Ruched Waist Mini Dress
Now 55% Off
Credit: Courtesy of AsosFor those days when October is inexplicably warm, go with a breezy, polka-dot dress that will remind you of those summer days. A beret will help you channel those fall vibes too.
17
A fun top and straight leg jeans
AGOLDE Lana Mid Rise Straight Jeans
17
A fun top and straight leg jeans
AGOLDE Lana Mid Rise Straight Jeans
Credit: Courtesy of ShopbopEveryone needs a good pair of straight-leg jeans in their closet. Try wearing yours with a leopard-print button-up and western-style boots.
18
A baby doll dress and boots
Sea Ruffled Broderie Anglaise-Trimmed Cotton-Voile Mini Dress
18
A baby doll dress and boots
Sea Ruffled Broderie Anglaise-Trimmed Cotton-Voile Mini Dress
Now 20% Off
Credit: Courtesy of Net-a-porterYou're about to see this dress silhouette everywhere, so get one now and be ahead of the trend while you can. And can we talk about how this burgundy color is the perfect shade for fall?
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19
A matching plaid set
Fe Noel Welfed Pant
19
A matching plaid set
Fe Noel Welfed Pant
Credit: Courtesy of Fe NoelWow, this PLAID! You can wear the pants and cropped shirt separately with other pieces, but honestly, his stylish set is too good not to wear together.
20
A patchwork maxi dress
GANNI Patchwork Printed Silk-Blend Satin Maxi Dress
20
A patchwork maxi dress
GANNI Patchwork Printed Silk-Blend Satin Maxi Dress
Credit: Courtesy of Net-a-porterHello, perfectly-layered outfit. Throwing a turtleneck under your favorite silk maxi will keep you (semi) warm in those dwindling temps. You can always add a coat if needed, but the patchwork on this dress is definitely meant to be seen.
Danielle is the Fashion Editor at Cosmopolitan, where she covers the American and British ready-to-wear markets and handles fashion for all cover and fashion stories in book and online. When she’s not working on print, she covers all the latest fashion trends and news for digital. Danielle started as a Fashion Intern for Cosmopolitan in 2016 and has been with the magazine ever since. Follow her journey in the fashion industry on Instagram.
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