Leo Looks

It’s F*%NG Cold Outside. Again. Here’s What To Wear.

Winter has doubled down this year. Here’s how to look great while staying warm—from our new favorite parkas and a perfect pair of boots, to Arnold Schwarzenegger’s badass 80s action movie watch. (And we won’t even make you ditch the sweats). 


Look “smart” but make it comfortable (i.e. elastic waist pants that look like your new favorite trousers).

Uniqlo Ultra Down Down Coat $100 / Alex Mill Mercer Sweater $98 / White Sand Pantaloni Con Banda 174€ / Frye Chris Boots $298 / London Sock Company Herringbone Socks $23 / Seiko Prospex “Arnie” Watch $550


We call this the “I was lounging at home but had to run out to walk the dog, and just threw on this killer parka.”

Alpha Industries Alpine Parka $250 / Mollusk Andover Sweater $128 / Todd Snyder + Champion Utility Cargo Sweats $168 / Nike Challenger OG $90 / RoToTo Socks $32 / Zodiac Super Sea Wolf GMT $1,795


Uniqlo Ultra Down Down Coat $100

Designed to be lightweight while incredibly warm thanks to bio-warming padding, has a water-repellent coating, and will keep even the slightest wind from entering.

Alex Mill Mercer Sweater $98

We’re all about this yellow ochre color, and this is fast becoming one of our go-to brands for cool basics. The soft-lightweight fabric will layer nicely under any jacket.

White Sand Pantaloni 174€

Ever since we tired of skinny pants (finally), this brand has become our go-to for that perfectly-slightly-baggy pant. The elastic waist replaces your chinos AND your sweats.  Ethically made by local craftsmen in Romagna.

Frye Chris Boots $298

Best looking rugged boot we’ve seen in a while.

London Sock Company Socks $23

Ilaria’s go-to sock brand for all her celebrity clients.

Seiko Prospex “Arnie” Watch $550

A reissue of the 1982 Hybrid Diver’s watch famously worn by Arnold Schwarzeneger in classic flicks like Predator and Commando. Still cool, even tougher, and updated with solar charging tech.

Alpha Industries Alpine Parka $250

The N-3B is the first jacket Alpha Industries produced for the U.S. military—designed in 1959 to protect air force ground and crew members from extreme cold. Bonus: the faux-fur hood is detachable.

Mollusk Andover Sweater $128

Surf-wear titan Mollusk represents everything that’s cool about beach culture and exceptional manufacturing quality. This handsome sweater is made in Peru from yarn-dyed cotton.

Todd Snyder + Champion $168

The body is based on Snyder’s bestselling Slim Jogger. The 20 oz Reverse Weave material is a pre-WWII technological marvel dreamed up by American coaches of the 1950s to keep their team’s uniforms in top shape and developed by Champion.

Nike Challenger OG $90

Nearly a 1-to-1 remake of the OG running shoe that offered runners a distinct look in the ’70s.

RoToTo Socks $32

Crafted and designed in Japan, made of undyed organic cotton, and uniquely thick due to the low gauge old-fashioned knitting machine used in their construction.

Zodiac Super Sea Wolf GMT $1,795

This Limited Edition watch is a modern rendition of Zodiac’s original 1966 Aerospace GMT model first imagined during the heart of the international Space Race. Sleek, powerful, and 100% Swiss made.