Ashley Olsen Wore the Jeans-and-Flats Outfit Every Cool New Yorker Swears By


Leave it to Ashley Olsen to show up to her birthday party, held at The Grill in NYC, in the most low-key jeans-and-flats combo and still manage to look like the coolest one in the room. To celebrate her 36th birthday, the designer of The Row casually paired a longline black blazer with a white T-shirt, distressed denim, and a pair of suede mocassin loafers—a four-piece combo that every stylish New Yorker just so happens to wear on repeat. Then again, you’d be hard-pressed to find a New Yorker who doesn’t, albeit unconsciously, want to dress like an Olsen twin. 

But get this: The best part about Olsen’s jeans-and-flats outfit isn’t just that she’s wearing it. Rather, it’s how easy it is to copy. Keep on scrolling to add every last piece of the birthday girl’s look, from her oversize blazer to her just-distressed-enough jeans, to your year-round wardrobe. As a New Yorker who already owns all four ingredients, I can say with certainty that you won’t regret it. 

It’s time to test-drive the low-rise-jeans trend already.

Agolde’s jeans are unmatched.

For this price, I’ll buy ’em twice. 

You can’t go wrong with 501s.

The perfect level of slouchiness.

From Ashley Olsen herself. 

Porte & Paire is every fashion person’s best-kept shoe secret. 

Easy, comfy, and well priced—these loafers do it all. 


These are worth the price every day of the week. 

Don’t underestimate Zara’s blazer selection.

Extra elevated. 

The perfect summer blazer, found. 

Every fashion editor owns this.

The all-time greatest topper for any simple look. 

I’m buying one in every color.

This crop is *chef’s kiss.*

If you want a boxier fit, this tee is for you. 


Simplicity is never boring. 

Coming up: Flats and Jeans Work Well Together—These Outfits Are Worth a Try

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