What To Wear With Your Hat

Chilly temperatures demand warm headwear, so chances are you have amassed quite a selection by this point. Rather than throwing on your hat with abandon, a few simple tips can help tie your outfit together and make it look less like an afterthought, and more like a centrepiece. Taking notes from Rosie Huntington-Whiteley and Kate Hudson, we have pulled together outfit ideas for a range of different hats, and some shoppable styling pieces to inspire you.

Rosie Huntington-Whiteley


Clint Brewer / Splash News

The military cap has certainly been making a comeback, and we love how Huntington-Whiteley embraced it’s ‘60s vibe by pairing hers with a flippy mini skirt, chunky Balmain Crew Neck Sweater ($1117) and Stuart Weitzman’s over-the-knee Highland Boots ($488). 



Sergio Rossi

Knee High Boot ($1486) in Black


Stockholm Skirt ($138) in Black Plaid 

Sarah Jessica Parker


Mario Magnani/Bauer-Griffin/GC Images

Not one to part with her stilettos, Parker recently stepped out in a leather jacket, skinny jeans and a playful, monogrammed Fendi Selleria Bag ($3600), but made sure to stay warm by donning a chunky knit pom-pom beanie.

Skinny Regular Jeans ($20) in Black

Kate Hudson


George Pimentel/Getty Images for Sundance Film Festival

At Sundance Film Festival, Hudson effortlessly pulled off après-ski style by wearing a faux fur trapper, a printed Line Knitwear Sweater ($295) in Highlow Maple, Isabel Marant Nowles Snow Boots ($840) and accessorizing with a red clutch and matching lip stain. 

LipSurgence Matte Lip Tint ($24) in Fiery Red 

Merino Chamonix Jumper ($195) in Navy 

Suki Waterhouse


Alo Ceballos/GC Images

To accompany her boyfriend Bradley Cooper to an event at the Sundance Film Festival, Waterhouse kept it simple by wearing a black skullcap, a chunky sweater dress, and her Timberland Women’s 6-Inch Premium Waterproof Boots ($180) in Rust. 


Women’s Nellie Chukka Double ($110) in Golden Beige 

Jessica Alba


GVK/Bauer-Griffin/GC Images

Alba tempered the menswear vibe of her blue Janessa Leone Sara Hat ($170) by pairing it with a feminine, printed scarf and a lipstick red Saint Laurent Classic Sac Du Jour Tote ($2590). 


D.D. Bag Medium Bowler Bag ($ 1595) in Orange 

A Peace Treaty

Oglron Scarf ($330)