10 Anti-Trend Autumn Outfits I Plan to Wear Over and Over

I don't know what it is about fall, but every year when October hits, I want to shun most trends in favor of all things classic. Simple, uncomplicated outfit combinations that require little effort are my goal. (Fall is a busy time of year, after all.) And luckily, finding new outfit inspiration that fits the bill has been very easy this season, in particular, as quiet luxury has been the overarching theme of 2023.

I figured I'm hardly the only one who's into "anti-trend" fall outfits, so I'm here to share some of the best classic looks I've come across as of late. As a disclaimer, although I'm using the term "anti-trend" here, you'll likely notice that some of the below outfits do contain current trends. But trends can also be classic, as many of them are right now (think ballet flats, oversize button-downs, and tweed jackets), so therein lies the explanation.

Scroll on to get inspired by 10 of my favorite classic fall outfits, and shop pieces needed to re-create them.

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Button-Down Shirt + Maxi Skirt
(Image credit: @sashi.mei)

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Tweed Jacket + Jeans + Kitten Heels
(Image credit: @anoukyve)

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Leather Jacket + White T-Shirt + Jeans + Ballet Flats
(Image credit: @lucywilliams02)

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Turtleneck + Long Leather Skirt
(Image credit: @tylynnnguyen)

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Denim Shirt + Trouser Jeans
(Image credit: @olympiamarie)

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Striped Sweater + Slip Skirt + Loafers
(Image credit: @annabelrosendahl)

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Button-Down Shirt + Tube Top + Jeans
(Image credit: @vikilefevre)

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Trench Coat + T-Shirt + Jeans + Boots
(Image credit: @styleidealist)

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Cardigan + Miniskirt + Slingback Flats
(Image credit: @tamaramory)

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Button-Down Shirt + Tank Top + Baggy Jeans + Sneakers
(Image credit: @eggcanvas)

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Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.