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.
30 Comfy, Cozy Transitional Outfits to Get You Through September in Style
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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.
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.
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.
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.
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)
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.
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.
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.
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.
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.
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.)
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)
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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!
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)
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 (
27. Go Classic With a Denim Boilersuit
28. Elevate Some Comfy Track Pants
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.
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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