30 Comfy, Cozy Transitional Outfits to Get You Through September in Style

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True autumn may not be here just yet, but we fully plan to spend this September leaning into all the best fall traditions—peeping leaves in the Northeast, apple picking with friends, cozying up in plaid from head to toe and indulging in pumpkin spice everything. Of course, refreshing our wardrobes is another annual fall activity we can’t wait to dive into. Here, 30 fabulously chic and easy September outfit ideas to inspire you all month long.

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woman wearing a floral maxi dress
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1. Make Your Face Mask Part of Your Outfit

You can’t go wrong with a plain blue or black, but opting for a fun color or print instead can help make your face mask actually feel like part of your outfit. Play around with mismatched prints, like the leopard spots and floral above, or go for a coordinated look by matching your mask to your dress or accessories.

Shop similar styles: Modenna Face Masks ($13); Chelsea28 Chiffon Maxi Dress ($99; $60); Steve Madden Ethos Sandals ($85)

woman wearing a cardigan over a dress
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2. Belt a Cardigan Over Your Dress

Layering a cozy knit over a flared dress can look a little bulky. Add a leather belt, though, and you're good to go. Tuck the front of your sweater into the belt itself, then leave the rest hanging loose to give your silhouette a bit more shape without sacrificing on comfort.

Shop similar styles: J.Crew Ribbed Cardigan ($128); B-Low the Belt Molly Belt ($140); Rails Ivy Shirtdress ($198); Journee Collection Taven Boots ($70)

woman wearing shades of brown
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3. Don’t Put Away Your Linen Pieces Just Yet

Transition your Coastal Grandmother summer favorites to fall by pairing them with darker neutrals rather than shades of white. Brown or black linen will keep you looking and feeling cool as we slowly (but surely) head into true autumn.

Shop similar styles: J.Crew Vintage Rib Tank Top ($35; $27); Reformation Vesta Pants ($178); Staud Ollie Shoulder Bag ($250); Birkenstock Arizona Sandals ($50)

woman wearing a pink dress
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4. Embrace the Tent Dress

If you haven’t already jumped on this oversize frock trend, now is the perfect time. Two things to keep in mind: Opt for a midi or mini length to avoid looking like you’re wearing a literal tent, and keep your accessories sleek and minimal.

Shop similar styles: ASOS Broderie Midi Dress ($248; $186); Kayu Mini Preston Bag ($135); Rothy’s The Loafer Shoes ($165)

tailoring and statement jewelry fall trends for women over 401
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5. Pair Chunky Jewelry with Tailored Staples

Tone down the office vibes of a sharp blazer or tailored suit by piling on gold statement jewelry. Now all you need are some easy sneakers and you’re ready for any stylish weekend event.

Shop similar styles: Everlane The ‘80s Blazer ($175); Madewell Northside Vintage T-shirt ($19); Mason & Madison Co. Chain Necklace ($125; $85); AUrate x Kerry Lioness Necklace ($550); Monica Vinader x Doina Chain Bracelet ($395); Nacre Lune 8 Gold Watch ($240)

woman wearing a floral jumpsuit
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6. Try a Floral Jumpsuit

Boilersuits and jumpsuits have been growing in popularity for a few seasons now, but the best way to rock one this fall is with a bold floral print and coordinating solid-colored accessories.

Shop similar styles: Farm Rio Wide-Leg Jumpsuit ($228); Kate Spade New York Smile Bag ($198; $139); Vagabond Alina Boots ($210)

woman wearing a cropped jacket
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7. Play with Proportions

Voluminous parachute pants are trending, and while you could pair them with a sleek bodysuit, a more fashion-forward approach is to opt for an oversize top as well. The key to making this combo work is to maintain some distance between the two pieces, meaning your top or jacket should hit right at the top of your pants or even show a little midriff.

Shop similar styles: Stradivarius Cropped Denim Jacket ($51; $39); Bershka Cargo Pants ($36; $26); Neous Lacerta Bag ($595); Unisa Miriam Sandals ($50)

woman wearing a black dress and pink shoes
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8. Dress Up a Simple LBD with Standout Accessories

Transform a simple black frock from basic to fabulous with the help of a few chunky chain necklaces and Barbie pink shoes. Of course, you could also opt for oversize statement earrings, animal prints or any other accessory that demands the spotlight.

Shop similar styles: Eliza J Fit & Flare Dress ($138); 8 Other Reasons Maddison Necklace ($36); Miranda Frye Brooklyn Necklace ($106); Nina Shoes 60 Heels ($99; $79)

woman wearing a sweater vest
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9. Wear a Trendy Sweater Vest as a Shirt

When you hear the term “sweater vest,” you likely think of Doug Funnie or a nerdy professor layering a cable knit version over a collared shirt or tucked into trousers. But the 2022 version is way cooler than that (no offense, Doug) and looks best when worn solo as a shirt itself. Add a pair of leg-lengthening flared jeans to the mix and you’ll be good to go.

Shop similar styles: Babaton Emporia Sweater Vest ($110); Lovestrength Wylie Belt ($92); AE Ne(x) Level Flare Jeans ($50); Marc Fisher LTD Zala Heels ($165; $83)

woman wearing all pink
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10. Try Barbiecore for Fall

Barbiecore was one of the biggest trends of the summer, and while hot pink pieces will definitely keep going strong well into autumn, the silhouettes will be quite different. Instead of party-ready Barbie, think more office-appropriate Barbie with blazers, trousers, oversize knits, midi skirts and button-up shirts replacing minidresses and crop tops.

Shop similar styles: Rag & Bone Charles Blazer ($550; $385); J.Crew Vintage T-Shirt ($30; $17); Topshop Satin Midi Skirt ($56; $45); Schutz Shalla Shoes ($118)

woman wearing a matching sweater and knit skirt
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11. Try a Coordinating Knit Set

Matching sweaters and knit skirts or cardigans and cashmere pants are by far the comfiest and chicest way to dress this fall. (Especially if you let a little midriff show in between the two.)

Shop similar styles: Ronny Kobo Jadey Knit Top ($328) and Ikra Knit Skirt ($298); Freedom Moses Lagoon Sandals ($45)

woman wearing a one-shoulder top
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12. Embrace ’70s-Era Accessories

Chain belts, silk hair bandanas and rhinestone hoops all give off major Disco vibes (especially when worn together). But if you pair them with modern staples, like sleek bodysuits and cargo pants, they suddenly feel super fresh and less like a costume.

Shop similar styles: Echo Vintage Stripe Silk Scarf ($59); The M Jewelers NY Large Earrings ($275); J.Crew FormKnit One-Shoulder Bodysuit ($40); Amazon Chain Belt ($17); Halara Cargo Pants ($45; $35); Jeffrey Campbell Saints Heels ($145; $110)

woman wearing a bucket hat
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13. Wear a Bucket Hat Like a (Stylish) Adult

This ’90s style is back once more, but rather than reach for a Kangol bucket and baby tee, try a Cottagecore twist on the trend. Opt for hats with a slightly wider brim that feature florals, gingham and pastel hues. As for the rest of your look, lean into the English countryside vibes with a puff-sleeve blouse or dress and loose waves or curls.

Shop similar styles: ASOS Fisherman Bucket Hat ($20; $9); Frame Puff-Sleeve Top ($198; $99); Sandro Paris Crossbody Bag ($245; $147); Lucky Brand High-Rise Jeans ($119)

woman wearing a trench coat and tall boots
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14. Let Rachel Green Be Your Fashion Muse (Again)

Both ’90s fashion and Friends nostalgia are in full swing this fall, so why not combine the two and use the show’s most stylish character as your sartorial inspiration? Tall, slouchy boots, pleated mini skirts, gray sheath dresses and, of course, hair that’s full of body and bounce are as chic now as they were when Rachel first wore them.

Shop similar styles: Sam Edelman Water-Repellent Trench Coat ($190); H&M Cropped Sweater ($30); Banana Republic Pleated Mini Skirt ($80; $60); Vince Camuto Parnela Boots ($239)

woman with a sweater tied around her torso
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15. Knot a Sweater Across Your Body

Tying a sweater around your hips isn’t all that flattering and draping one over your shoulders can feel a bit too preppy for some. The solution? Go for a crossbody effect and knot your pullover across your front instead.

Shop similar styles: Vero Moda Pastel Stripe Sweater ($54); Old Navy UltraLite Tank Top ($15); Agolde ‘90s Mid-Rise Jeans ($178); Journee Collection Rianne Sandals ($50)

woman wearing a black sweater and gold slip skirt
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16. Do ‘90s Grunge the 2022 Way

Yes, you can make grunge look grown up. Opt for an oversize knit with cut-outs or fringe that feel more purposeful and less distressed and layer it over a luxe slip skirt or dress. Choose equally elevated accessories—like embellished slide sandals, a sleek clutch and pearl drop earrings—to finish the look.

Shop similar styles: Mejuri Oversize Pearl Earrings ($65); Valentino Cutout Wool Sweater ($1,980); Vince Side Slit Skirt ($295); Steve Madden Ilana Sandals ($90; $50)

17. Give Your Bike Shorts a Chic Monochrome Makeover

Bike shorts are not just for the gym, nor should they be relegated to only being worn under oversize tees or cozy sweatshirts. Pair them with a matching fitted top, blazer and sleek accessories and you’ve got yourself an impressively chic ensemble centered around our new favorite casual wardrobe staple.

Shop similar styles: Quince Cotton Blazer ($70); Skims Fits Everybody Bodysuit ($58); Everlane Perform Bike Shorts ($48); Madewell Sydney Hobo Bag ($118); Reformation Cora Coil Sandals ($278; $84)

18. Wear a Shirtdress Over Jeans

Unbutton the hem to just above the waist of your jeans to create a more dynamic silhouette and finish with either a statement necklace or some bold earrings.

Shop similar styles: Chico’s Adjustable Scarf Necklace ($70; $53); Nasty Gal Button-Down Shirt Dress ($78); Warp & Weft ASE Straight-Leg Jeans ($98)

19. Try a Breathable Sweater Dress

It may not be full-on cozy sweater season just yet, but that doesn’t mean you can’t rock a comfy knit dress anyway. Opt for a lightweight design (preferably in a natural fiber) or one with a looser weave to ensure you won’t overheat.

Shop similar styles: Staud Shoko Striped Sweater Dress ($195); JW Pei Gabbi Bag ($89); Dolce Vita Nyx Sandals ($80; $60)

woman wearing green denim
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20. Opt for a Matching Denim Set

Think of a matching jacket and jeans combo like a denim jumpsuit...only you don’t have to get completely undressed every time you go to the bathroom. Yes, you could always go for a classic blue-wash denim, but this year we’re loving less expected options like acid-wash or bright hues.

Shop similar styles: AFRM Magda Jacket ($98) and Fez Jeans ($68); Cotton On Rib Crew T-shirt ($20); Little Liffner Slanted Mini Tote ($420); Lulus Julie Sandals ($38)

woman wearing a black tee and floral skirt
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21. Swap Your Mini Skirt for a Maxi

Longer hemlines are in this season, but we promise they’re just as easy to wear as summer minis. The most foolproof combo is a basic T-shirt, patterned maxi and basic sandals or flats. Opt for a maxi that shows a little bit of leg, by way of buttons that can be undone or a knee-high slit, to avoid overwhelming your frame with all that fabric.

Shop similar styles: Marine Layer Swing T-shirt ($45); MinkPink Serena Skirt ($139); Steve Madden Ethos Sandals ($85)

woman wearing a black blazer
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22. Dress Up Trendy Cargo Pants

Dress up a pair of trendy cargo pants by styling them with a sharply tailored blazer and some posh ballet flats. It will instantly make this super casual style feel more appropriate for work or a dinner date.

Shop similar styles: A New Day Double-Breasted Blazer ($38); Pull&Bear Cargo Pants ($46); Alohas Sway Leather Flats ($140)

woman wearing all denim
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23. Update Your Canadian Tuxedo

Wearing denim with denim (aka, a Canadian tuxedo), is one of our favorite fall outfit go-to's. But this Y2K-inspired take on the classic is inspiring us to swap our old trucker jackets and skinnies for knotted dark-wash shirts and bootleg jeans. Oh, and don’t forget the denim bucket hat, too.

Shop similar styles: Mirmaru Denim Bucket Hat ($13); AG Cade Denim Shirt ($188); Good American Good Legs Flare Jeans ($150); Nine West Workin Heels ($89)

woman wearing all green
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24. Fake a Cardigan with a Strategically Wrapped Scarf

Transforming your beloved pashmina into a chic new cardigan is easier than you might think. Wrap a wide scarf over your shoulders, then take the right side and pull it across your body tucking it partially into the front of your waistband and leaving the end to drape behind you. Repeat with the left side, and voilà!

Shop similar styles: Treasue & Bond Fringe Scarf ($39); J.Crew Relaxed-Fit Poplin Shirt ($90); Old Navy Wide-Leg Pants ($40); Sam Edelman Orchid Sandals ($140)

a woman wearing a stripe sweater
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25. Take Your Summer Staples for One Last Spin

Nantucket-inspired blue-and-white striped knits, straw totes, easy slide sandals, raw-hem light-wash denim—these are just a few of our favorite summer go-to’s. Give them all one last run before you stow them away for the season in favor of cozier pieces, like shackets and leather pants.

Shop similar styles: Alex Mill Button-Back Sweater ($135); Summersalt Perfect Boyfriend Shirt ($75); Agolde Pinch Waist Kick Jeans ($188); Furla Meraviglia Straw Bag ($288); Tory Burch Double T Slide Sandals ($198)

woman wearing two blazers
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26. Layer Your Blazers

We love a good outerwear layering hack, and while we usually suggest pairing two different styles, this look has convinced us just how chic doubling up on one silhouette can really be. Opt for lightweight fabrics to avoid overheating, and try to mix one patterned blazer and one solid hue rather than lots of prints all at once.

Shop similar styles: Treasure & Bond Patch Pocket Blazer ($99); Topshop Mensy Blazer ($102); Wilfred Only Turtleneck ($48); Everlane The Fatigue Barrel Pants ($88); Dr. Martens 1460 Boots ($160; $106)

27. Go Classic With a Denim Boilersuit

This easy wardrobe staple will never be out of style. Wear it with brown leather loafers and a coordinating handbag to really lean into that timeless look.

Shop similar styles: Sezane Brooklyn Jumpsuit ($215); Call It Spring Aliya Bag ($30); M.Gemi The Pastoso Loafers ($228)

woman wearing white track pants
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28. Elevate Some Comfy Track Pants

Get more use out of the gym staple by pairing it with a cashmere sweater and a structured mini bag.

Shop similar styles: Tory Burch Merino Sweater ($298; $199); N.Peal Striped Track Pants ($450; $315); Rebecca Minkoff Edie Chevron Bag ($248); Birkenstock Arizona Sandals ($130)

woman wearing a denim shacket
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29. Try a Denim Shacket

Combine a classic autumn topper with the new kid on the block and sport a denim shacket rather than a trucker jacket or plaid shacket. They’re just as versatile as the other two, but feel a bit fresher and more modern overall.

Shop similar styles: Good American Denim Redesign Shacket ($129); Uniqlo Crewneck T-shirt ($15); ASOS Cargo Pants ($42); Everlane ReLeather Velcro Court Sneakers ($110; $44)

woman wearing plaid blazer and jeans
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30. Go Back to Basics with a Plaid Blazer

A plaid blazer, jeans and ankle boots—no, this isn’t the trendiest outfit on the block, but it will always look chic and pulled together. Keep this ‘fit in your arsenal for days when you need something quick, comfy and stylish to whip out at a moment’s notice.

Shop similar styles: Maeve Double-Breasted Blazer ($170); Madewell Northside Vintage T-shirt ($19); Pilcro Slouchy Wide-Leg Jeans ($148); Mansur Gavriel Lilium Bag ($745; $447); Charles & Keith Ankle Boots ($83)

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Abby Hepworth


Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...
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