The Best Friend Experience with Jenny Mollen

The Best Friend Experience with Jenny Mollen

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The Best Friend Experience with Jenny Mollen
The Best Friend Experience with Jenny Mollen
How To Dress a Guy

How To Dress a Guy

(BECAUSE NOBODY ASKED ME, AND I HAVE THOUGHTS!)

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JennyMollen
Jul 15, 2025
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The Best Friend Experience with Jenny Mollen
The Best Friend Experience with Jenny Mollen
How To Dress a Guy
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Ever since high school, when I used to show up to school wearing a suit with suspenders, I’ve gravitated towards men’s fashion. I don’t know what it is about the silhouette of a tailored pair of black slacks or the sex appeal of a denim button-down, but I find men’s fashion timeless, effortless, and just the slightest bit superior. Sort of like men... if they were women. It’s always such a pet peeve when I see something I love in the men’s section, only to hunt down its female counterpart and find it cropped, tailored at the waist, and bejeweled with the kind of rhinestones that scream, “I fucking DARE you to wash me in the dryer!”

My husband has a slightly preppy style, and my two sons still don’t give a shit about fashion unless it involves a Nike swoosh or a Spotify logo.

However, if I were suddenly tasked with dressing the other members of my household, here would be the options.

MONOCROMATIC - Think Scandinavian street style

  • Vibe: Clean, modern, and confident.

  • Pieces: Black slim-fit jeans, black t-shirt or turtleneck, tailored black coat or bomber, black boots or sneakers.

  • Inspiration: Hot artistic type, Creative director who doesn’t have time to fuss over himself, he wants you to be the loud one.

LINEN PANTS - Coastal / Resort Chic

  • Vibe: Sophisticated yet breezy — like you sip Negronis by the sea.

  • Style It With: White linen shirt (maybe unbuttoned a bit), leather sandals or espadrilles, tortoiseshell sunglasses.

  • Occasion: Beach wedding, summer vacation, rooftop dinner.

  • Inspiration: He doesn’t speak English, and you don’t want him to.

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