18 Cozy Transitional Outfits to Keep You Comfortable and Stylish Through September.

18 Cozy Transitional Outfits to Keep You Comfortable and Stylish Through September. post thumbnail image

Although true autumn may not have arrived yet, we fully intend to spend this September embracing all the best fall customs, including leaf-peeping in the Northeast, apple-picking with friends, cosiness in all things plaid, and indulging in pumpkin spice everything. Of course, another fall tradition we eagerly await is updating our outfits. Here are 30 fantastically stylish and simple clothing ideas for September to get you motivated.

1. Consider include a face mask in your look.

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While wearing a plain blue or black face mask is always a good idea, adding a bright colour or print can help your face mask feel more like an integral part of your overall look. A coordinated style can be achieved by matching your mask to your clothing or accessories, or you can experiment with clashing prints like the leopard spots and floral seen above.

2. Over your dress, belt a cardigan.

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It may appear a touch hefty to wear a comfortable knit over a flared dress. But all you need is a leather belt, and you’re ready to go. To add a little more structure to your appearance without compromising comfort, tuck the front of your sweater into the belt and leave the rest hanging loose.

3. Don’t store your linens just yet.

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Instead of using white, turn your Coastal Grandmother summer faves into fall-appropriate neutrals. As we slowly (but surely) transition into the genuine autumn season, wearing brown or black linen will keep you looking and feeling cool.

4. Adopt the Tent Dress.

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The time is now to embrace the oversize dress trend, if you haven’t already. Consider choosing a midi or mini length to prevent appearing to be wearing an actual tent, and keep your accessories simple and sleek.

5. Combine chunky jewellery with tailored basics.

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Add lots of gold statement jewellery to soften the business feelings of a smart jacket or cut suit. All you need now to attend any fashionable weekend event are some comfortable sneakers.

6. Pick up a floral jumpsuit.

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Jumpsuits and boilersuits have become more and more fashionable over the past few seasons, but the ideal way to wear one for fall is with a striking floral print and matching solid-colored accessories.

7. Accessorize a Simple LBD with Bold Accessories.

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With the aid of a few hefty chain necklaces and Barbie pink shoes, a plain black dress may be transformed from basic to beautiful. Of course, you may also choose oversized statement jewellery, prints with animals, or any other accessory that demands attention.

8. Use a trendy sweater vest in place of a shirt.

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You probably picture Doug Funnie or a geeky professor wearing a cable-knit sweater vest tucked into his pants or layered over a collared shirt when you hear the term “sweater vest.” Although I don’t mean to offend Doug, the 2022 version is more cooler and looks best when worn by itself as a shirt. You may complete the look by adding a pair of flared jeans that elongate the legs.

9. Use Barbiecore this fall.

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Barbiecore was one of the greatest trends of the summer, and although bright pink pieces will undoubtedly be popular far into the fall, the silhouettes will be very different. Think more office-appropriate Barbie rather than party-ready Barbie, with blazers, slacks, oversized knits, midi skirts, and button-up shirts in place of minidresses and crop tops.

10. Try a matching knit set.

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The most comfortable and stylish way to dress in fall is with coordinating sweaters and knit skirts or cardigans and cashmere pants. (Especially if you allow a small amount of belly to show between the two.)

11. Adopt accessories from the 1970s.

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Chain belts, silk hair bandanas, and rhinestone hoops are all majorly Disco-inspired accessories (especially when worn together). However, if you wear them with contemporary essentials like bodysuits and cargo pants, they suddenly feel quite current and less like costumes.

12. Dress Like an Adult by Donning a Bucket Hat.

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This ’90s trend is back, but this time attempt a Cottagecore spin on it rather than reaching for a Kangol bucket and baby tee. Choose hats with a slightly larger brim and floral, gingham, or pastel patterns. To complete your style, wear a puff-sleeved blouse or dress with free-flowing curls or waves to channel the English countryside.

13. Wrap yourself in a sweater in a knot.

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While draped over the shoulders can feel a little too preppy for some, tying a sweater around your hips isn’t really flattering. The remedy? Instead of tying your pullover across your front, go for a crossbody look.

14. Dress Shirtdress Over Jeans.

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To create a more dynamic look, unbutton the hem of your jeans to just above the waist and accessorise with a dramatic necklace or some striking earrings.

15. Try a Sweater Dress that Breathes.

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You can still look great in a cosy knit dress even though it’s not yet comfortable sweater season. To prevent overheating, choose a light-weight design (ideally made of natural fibres) or one with a looser weave.

16. Wear fashionable cargo pants 22.


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Fashionable ballet flats and a sharply fitted blazer can dress up a pair of trendy cargo pants. It will immediately elevate this extremely casual look to the level of professional or date night attire.

17. Combine Your Blazers.

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Although we generally advise layering two different designs of clothing, this outfit has shown us just how stylish it can be to double up on one silhouette. We love a good layering trick for outerwear. Choose breathable materials to prevent overheating and attempt to combine one patterned blazer with one solid colour rather than a number of designs at once.

18.  Try a Denim Shacket.

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Wear a denim shacket in place of a trucker jacket or a plaid shacket to combine a traditional autumnal top with the newest kid on the block. Although they are equally as adaptable as the other two, they have a more current and fresher vibe overall.

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