Jennifer Lopez : A Pinned Side
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Guy's Opinion: "I like the asymmetry. It's classic, but with a twist that emphasizes your best angle." ; Photo: Getty
Josephine Skriver : A Messy Ponytail
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Guy's Opinion: "She looks low-maintenance, like a girl who doesn't spend hours getting ready and is always down for an adventure." ; Photo: Getty
Rosie Huntington-Whiteley : Tousled Waves
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Rosie Huntington-Whiteley
Guy's Opinion: "Simple, elegant, natural. More 'summer in Provence' than 'I spent an hour messing with my 'do.'" ; Photo: Getty
Lily Aldridge : Pigtail Braids
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Guy's Opinion: "Pigtails say schoolgirl and schoolgirls remind us of our youth—it's every guy's fantasy." ; Photo: Getty
Gigi Hadid : A Slick High Ponytail
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Guy's Opinion: "This look is like a throwback to the cheerleader in high school I could never get: Preppy, all-American and out of my league (which makes me want her even more)." ; Photo: Getty
Alexa Chung : Bedhead Bangs
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Guy's Opinion: "She's got attitude. The short hair is messy in a hot, rock 'n' roll way." ; Photo: Getty
Emma Stone : A Side-Parted Ponytail
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Guy's Opinion: "Sexy politician." ; Photo: Getty
Olivia Palermo : Long & Straight
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Guy's Opinion: "I like long hair so this is my favorite. The center part gives a hippie vibe." ; Photo: Getty
Ciara : A Piece-y Updo
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Guy's Opinion: "I like it because it has a sexy, just-rolled-out-of-bed-or-finished-a-jog kind of look while still looking clean and stylish." ; Photo: Getty
Chrissy Teigan : A Loose Braid
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Guy's Opinion: "This is sexy because it makes me think of laid-back surfer girls, the kind you would quit your job and run away to a beach town for." ; Photo: Getty
Suki Waterhouse : A Piled Top Knot
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Guy's Opinion: "Fierce ballerina."
; Photo: Getty
Blake Lively : Major Volume
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Guy's Opinion: "It's retro, but not dated. She seems like she'd be the life of the party."
