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11 Style Updates Best for Showing Up Chic in September 2021

Transitional pieces are what to wear in fall fashion in September 2021 for work, off-duty or vacation, including knits, coats and more.

Are you staring into your closet and wondering what to wear in September 2021? We’ve got ideas and style inspiration on what to wear in September 2021 whether you’re working from home, heading back to the office, working out, hanging out, or even taking a vacation. September is all about transitions: the end of summer, the start of fall, back to school, fall weddings and more. So we’re thinking spice colors in light fabrics that are easy to layer. Here are some of the best transitional pieces – what to wear in fall fashion in September 2021 for work, off-duty or vacation, including knits, coats and more.

what to wear in September 2021?

New month, new opportunities to play around in the world of fashion. Yay! This September, we’re focused on transitional pieces that will take us seamlessly from summer into fall. And perhaps from home back into the office. Or from social distance to Old School socializing (if only!)

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The uncertainty of what to expect day to day with coronavirus protocols, expectations about work wardrobes, finicky fall weather – all of it leads us to layering. If you have no idea what the day will bring, best to prepare for, well . . . anything.

Transitional pieces are what to wear in fall fashion in September 2021 for work, off-duty or vacation, including knits, coats and more.

Transitional pieces are what to wear in fall fashion in September 2021 for work, off-duty or vacation, including knits, coats and more.

Happily, there are terrific knits and other layering options aplenty right now. We had a serious amount of fun scouring the shopping sites for the best of the season.

easy style updates to show up chic in September 2021

From classic wardrobe essentials to of-the-moment accessories, here’s what to wear this month to stay cool, crisp and chic all September long.

1. what to wear September 2021: The Dress.

Boss women will appreciate the ease and elegance of this dress from Austrian designer Lena Hoschek. It’s made of a breathable wool blend fabric perfect for autumn days at the office.

BUY NOW: $1,070.

2. what to wear September 2021: The transitional knit top.

This ribbed-knit top from DoDo Bar Or is a perfect transition piece from summer to early fall.

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

BUY NOW: $475.

3. what to wear September 2021: The breezy mini dress.

For those planning to hang onto the summer vibe deep into the fall, this cotton mini dress from Ulla Johnson checks all the boxes: summer weight, autumn colors.

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

BUY NOW: $445.

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4. what to wear September 2021: the cropped sweater and midi skirt.

This Brock Collection cropped sweater and midi skirt keep the look of the summer going into the fall season.

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

 

BUY NOW: Cropped sweater: $725. Midi skirt: $890.

5. what to wear September 2021: the cashmere joggers.

Totême’s cable-knit stretch-cashmere beige sweatpants are a perfect way to level up your loungewear game while keeping that comfy work-from-home vibe going all season long.

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

BUY NOW: $670.

6. what to wear September 2021: The Cape.

Call us crazy, but we’ve been secretly eyeing capes for a few seasons now, wondering if we could actually pull one off. The cool, breezy days of September seem perfect for the subtle drama of Totême’s camel cape. For a grand entrance into a new season, what could be better than this?

BUY NOW: $

7. what to wear September 2021: The shoulder bag.

A hot trend from summer 2021 that is definitely going to continue into the fall is the return of the baguette bag and its cousin, the slim shoulder bag. So you could consider this burnt-orange leather “Mount” bag from Bottega Veneta both a splurge and an investment. If you want.

 

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

BUY NOW: $

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8. what to wear September 2021: the canvas tote.

Rue de Verneuil’s brown and cream Traveller tote is lightweight and practical – and also very pretty. It’s handmade in Paris from Oxford canvas, with leather-trimmed top handles and a detachable shoulder strap.

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

BUY NOW: $262.

9. what to wear September 2021: the necklace.

We love the casual elegance of this choker from Cult Gaia. The leather-wrapped discs have a macramé vibe, but the overall effect is all in work-ready. It also comes in a neutral beige, but we’re swooning for the chic statement it makes in black.

BUY NOW: $120.

10. what to wear August 2021: the faux shearling slide.

Everywhere we look, we see winter white shearling. It’s on handbags, boots, jackets and more. What’s up with that? If you want to be on-trend and also a bit subversive, maybe opt for a pair of faux shearling slides, like these from Flattered.

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

BUY NOW: $130.

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11. what to wear September 2021: the stompy boots.

The stompy boot is still with us, and few brands do it better than Bottega Veneta. Take, for instance, this “Lug” boot from the fall winter 2021 collection. It’s sturdy, well-made, and the white and black colorway will go with absolutely everything you already own.

What to wear in luxury designer fashion September 2021 for work, vacation and weekend

BUY NOW: $1,100.

what to wear to be autumn chic in September 2021

That’s our take on what to wear in fall fashion in September 2021 for work, off-duty or vacation: transitional pieces that layer beautifully, including knits and coats. Plus accessories that will refresh your wardrobe (and your mood) as we head into a new season. What do you think, dear reader? Are you ready for September?

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This article contains affiliate links to products independently selected by our editors. As an Amazon Associate, Dandelion Chandelier receives a commission for qualifying purchases made through these links. 

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