Finally: A New Legging Outfit Idea, Courtesy of Sienna Miller

We know, we know—it's all about bike shorts these days. But the fact of the matter is that it's there's already a chill in the air, and shorts aren't exactly conducive to warmth, which is why it's time to pull out the ole leggings again. That's exactly what Sienna Miller just did in NYC, where temperatures are currently in the low 50s. Lo and behold, just when we thought we'd seen every cool fall legging outfit combination imaginable, Miller stepped out in one that actually feels fresh (which shouldn't exactly be surprising, given her impeccable style skills).
Miller ditched the typical hoodie-and-sneakers look, instead opting for a cute newsboy hat, bomber jacket, sweater, and Birkenstock clogs with her leggings. It's the sort of easy, cozy outfit that we'd gladly wear at some point during every fall weekend, whether or not we're heading to or from a workout. Keep scrolling to shop the pieces you need to copy Sienna Miller's legging look.
On Sienna Miller: Brixton Ashland Fisherman Cap ($42); Ellie Mae Esmeralda Sweater ($265); Birkenstock Boston Genuine Shearling Lined Clogs ($165)
Get the Look
Shop More Navy Leggings

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 arts. 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.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.
-
The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This Fall
It's all about this styling trick.
-
I'm an NYC-Based Dad Who Is Always on the Move—This Is How I Redefined My Everyday Wear
Effortless, easy, and cool.
-
Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do Too
See how fashion people from NYC to Paris to London wear them for fall.
-
This Classic Shoe Is Every Parisian's Secret to Making Jeans Look Elevated in Fall
And you probably already own it.
-
The Easy-Yet-Elevated Outfit Formula Fashion People Will Be Wearing Straight Into Fall
Here are seven takes on the chic look.
-
It's Official: This Is the Flat-Shoe Trend to Wear With Fall 2025's Most Popular Legging Color
As seen in Los Angeles.
-
From Basic to Designer: This Outfit Trend Will Instantly Make Your T-Shirts Look The Row Coded
Pinky promise.