When should you go for a wide brim? When is a sporty baseball cap appropriate? How do you play with color? Click through now for all the expert answers, and then shop our curated hat picks!
“Here, the wider brim balances out the flare of her denim. It's all about proportion.”
On Rachel: Calypso hat; Tom Ford glasses; Isabel Marant top; Rachel Zoe jeans; Hermes cuff; Anita Ko bracelets and ring; vintage Givenchy necklace; Gucci bag.
“With an easy, all-black ensemble, anything goes—it's like a clean canvas. So the bright, head-turning style here kind of steals the show.”
“The biker cap and bright red clutch turn a sleek black trench into rock-and-roll chic.”
“When you're a bit on the petite side, a medium-brim fedora can add some height to your appearance.”
“Positioned further back on her head, this bowler hat adds a really nice frame for her face. It looks effortless, as if she just tossed it on before she walked out the door.”
On Jessica: Twenty Tees Ponte Color Blocked Blazer ($238)
“You can rock a sporty ball cap and still look polished. Just balance it out with some dressier pieces, like a neutral pointed heel. And since she has a pixie cut, those large hoops adds the right dose of femininity.”
On Rihanna: House of Malakai Military Trucker Cap ($169); Alexander Wang sweater; J Brand pants; Manolo Blahnik heels.
“A simple shape in the same tonal family is a super easy way to polish off a casual look.”
On Rosie: Maison Michel hat; Chanel sunglasses; The Row sweater; Isabel Marant jeans; Balmain bag; Aperlai heels.
Elyse Mod Cap ($253) in Black
Shetland Baseball Hat ($41) in Grey
Wool Hat ($18) in Black
Lucy Hat ($140) in Grey
No Promises Fedora ($44) in Black
Felt Fedora ($38) in Black
Andre Rabbit Felt Trilby Hat ($450) in Neutral
Floppy Brim Fedora ($175) in Black
Ava Felt Trilby Hat ($115) in Burgundy
Hand Made Woollen Hat ($60) in Blue Marl
Velvet Ribbon Wool Fedora ($40) in Stone