30 Comfy, Cozy Transitional Outfits to Get You Through September in Style
Typically this is the time of year we’d be refreshing our jacket collection and investing in a new pair of chic fall boots. But we haven’t experienced a “typical” month in quite a while now. Just like last fall, we’ve got a lot of things on our minds (questions about back to school, attempting to plan safe holiday travels, hunting for disinfecting wipes), getting dressed in something that’s both cute and comfy can do a lot for our mental wellbeing and make us feel that much more put together. So, without further ado, here are 30 easy, comfortable, Zoom call-ready outfits to get you through the first month of fall in style.
1. Coordinate Your Face Mask with Your Accessories
2. Belt a Cardigan Over Your Dress
Layering a cozy knit over a flared dress can look a little bulky. But not if you add a leather belt! 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. Try a Sporty Tennis Skirt
Pleated sport skirts (with very convenient built-in shorts underneath) are a big trend for fall, particularly if you pair them with an equally sporty crewneck sweater and some fresh white kicks.
4. 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.
5. 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, like Coco Bassey’s caramel lace-up sandals and handbag to match.
6. Swap Your Bike Shorts for Denim Bermudas
If you just can’t figure out how to wear bike shorts outside the gym (you’re not the only one), why not swap them for a pair of Bermuda shorts instead? Follow Shanna Battle’s lead and tuck a trendy puff-sleeve blouse in to emphasize your waist and finish with a pair of leg-lengthening pointy-toe ballet flats.
7. 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 dainty floral print and a cinched belt. Isn’t that right, Liz Teich?
8. Dress Up a Simple Slip with Jewelry
Pile on the delicate chains, stacked rings, pretty pendants and gold hoops à la Coterie member Tyla Lauren Gilmore and your silky slip won’t look like an undergarment or nightgown anymore.
9. Layer a Turtleneck Under a Slinky Slip Dress
This two-part outfit is great for when the temperature starts to drop, but also for making your favorite easy house dress feel more WFH appropriate, especially for any last-minute video calls.
10. 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 2021 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.
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.)
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 and ones featuring 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. Choose a Sweatshirt with Flare
Swap your college hoodie for an upgraded sweatshirt, one with fringe, embroidery or glittery embellishments, instead. It doesn’t matter if you end up layering it over a sporty mini skirt à la Katie Sturino, or keep things even more low-key with some basic leggings, a funky sweatshirt will look much more put together than a gym-ready style.
17. 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.
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 we’re really loving Taye Hansberry’s gray acid-wash set to shake things up.
22. 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.
23. Use Autumnal Accessories to Transform Your Summer Dresses
A gray suit vest, brown leather handbag and schoolgirl loafers are all you need to transform a flowy summer frock into one that feels more seasonally appropriate for apple-picking and pumpkin spice latte sipping.
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.
26. Add Drama With a Long Robe
Even if the rest of your outfit consists of pajama pants and an easy tank, topping it off with a flowing robe, like Ijeoma Kola’s here, adds a dramatic flare that will make you feel significantly more dressed up.
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, a là Coterie member Babba Canales to really lean into that timeless look.
28. Wear Head-to-Toe Winter White
Monochrome ensembles can often look more expensive and luxe than multi-hued outfit, but this is especially true when it comes to creamy winter white. Yes, even if your look is comprised of a chunky knit and loose, pajama-esque pants.
29. Give Dark Academia a Whirl
This fun fall trend is one all generations can enjoy and pulls inspiration from the uniforms of Hogwarts students, dark mysterious libraries and preppy Northwestern college staples. And maybe a slight touch of Heathers for good measure.
30. Mix Moody Florals with Dark Plaids
The easiest way to mix mismatched prints is to pick ones that use the same color combinations—in this case navy lue and rust red. Plaid of all types and dark, moody florals are two of the most popular autumn patterns, so start with pairing these two classics and finish with some sleek ankle boots.