Jennifer Aniston’s Shoes Made Her Puddle Jeans 10X More Chic

I’ve been admiring Jennifer Aniston’s style for as long as I can remember. So whenever she steps out—especially in jeans—you can be sure I’m paying close attention.

Denim forms the backbone of my own wardrobe. I reach for jeans at least five days a week (in fact, I’m sitting in my favourite pair as I type), so I’m always ready to be inspired by a fresh take on the classic. Needless to say, when I spotted Aniston out in New York this week wearing a chic silhouette, I took note.

Sidestepping the season’s ubiquitous stovepipe styles—and long past the skinny jeans she once favoured—Aniston opted instead for a slim-cut pair that gently puddled around her ankles. The subtle pooling gave her look a relaxed, insouciant edge that, though it remained streamlined through the leg, offered just enough length to create that coveted slouch.

Of course, puddle jeans live or die by their shoe pairing. Too flat, and the hem risks dragging; too delicate, and it disappears entirely beneath the fabric. Aniston’s solution? A thick-soled black heeled boot. The added height accommodated the full sweep of the denim, while the sturdy silhouette anchored the look and lent a sharper finish. Where trainers might have felt overly languid and Mary Janes lost under the excess fabric, her boots made for the perfect pairing.