Style

5 Ways I'm Wearing Baggy Levi's This Fall

One pair of jeans, five outfits, and a very strong opinion about cuffing them.

September 20, 2026 · Filed under Style
Whitney wearing baggy light wash Levi's 501 jeans and an oversized cream sweater, leaning against a brick wall

I did not expect to become a baggy jeans person. For years I lived in skinny denim and told anyone who'd listen that I "didn't have the legs" for anything roomier. Then I bought these on a whim, wore them four days in a row, and quietly retired every other pair of jeans I own.

Here's what's actually holding these together as a wardrobe workhorse: they go from errands to date night with nothing but a shoe and a top change. Below are the five ways I've styled them most this month, plus everything you see pictured.

1. Errand Running

A plain white tee, the gold hoops I never take off, and my beat-up sneakers. This is the outfit I default to when I have four stops to make and zero interest in getting dressed twice.

2. Coffee Shop

Cuffed once at the ankle, paired with the cropped cardigan and a pair of loafers. Looks intentional, took ninety seconds to put together.

"The best outfit is the one you don't have to think about twice."

3. Work From a Cafe

An oversized blazer thrown over a simple tank turns these into something I'd wear to a client meeting without a second thought.

4. Date Night

A silky camisole tucked in, heeled boots, and the good earrings. Slouchy on the bottom, polished on top is my whole personality lately.

5. Fall Weekend

The chunky sweater, tucked in just at the front, with the fall boots I've now worn in three separate posts. No notes.

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