How to wear boyfriend jeans in the winter

Look 1: J.Crew blue jeans //Aéropostale socks //Dolce vita shoes

Look 2: Current Elliott capri //Forever 21 crew socks //Desert boots

Look 3: Gap stretch pants //  Dorothy Perkins socks // Grenson leather shoes



I have a few pairs of “boyfriend” style jeans, khakis and a pair of cigarette length black pants, but it is becoming winter here in Vermont and I am finding it very hard to keep those in my wardrobe rotation. Any suggestions on what shoes/boots or any other way to wear those shorter styles of pants and stay warm at the same time?

-Vicki, Vermont


Dear Vicki,

First of all, kudos to you for getting the most out of your wardrobe by trying to wear it in all seasons. I think us North-Easters should get a tax break when it comes to clothing because we essentially need two wardrobes; one for the warm months and one for the cold.

That being said, you may have to tailor how you wear the pieces that you carry over to all seasons, like your boyfriend jeans that you probably are used to wearing with sandals, flats and heels.

“Boyfriend” style pants are called just that because they aren’t quite as flattering as say your cigarette black pants and are more boyish. My recommendation would always be to make sure you juxtapose that with something a bit more feminine and flattering to avoid looking like you’re “Just One Of The Guys.” Yes, I just made a reference to the 1985 cult classic—watch it if you want inspiration on dressing like a guy but still obviously look like a girl.

If you want to still look feminine though, try wearing heeled booties with these pants if you can. This will elongate your legs and make them appear leaner than if you wore them with a flat boot. A stiletto bootie is a fun way to dress these pants up from day to night, but a stacked heel will be more comfortable and casual. If you absolutely must do a flat, try a desert boot or brogue that have a slight heel and are long, round in the toes.

If you are still dreadfully cold, a cute thin sock that you won’t mind showing (but aren’t too crazy or distracting) is okay to peek out of the top of your boots.

Whatever you do, make sure you roll up the hem, avoid thick socks, which will make you look like you actually transported to the 80’s, and don’t try squeezing those loose pants into tall boots.