Style 911: What Shoes To Wear With Boyfriend Jeans?

“I recently bought a pair of boyfriend jeans that I love, but I have no idea what shoes to wear with them. Booties? Stilettos? Keep in mind that I live in Wisconsin, so flip flops, sandals or anything similar will not be a possibility in the freezing winter months!” – Meghan

Hey Meghan, boyfriend jeans are super cute but you definitely don’t wanna go and ruin a good thing with a pair of Uggs, ya know? (No offense to them — we wear Uggs all the time. In our house.) A couple ideas for you, after the jump! Recently, Ralph Lauren paraded a whole slew of bf jeans down his spring 2010 runway, so you can rest assured this trend isn’t going away any time soon. He paired the denim with dainty, strappy heels, which is certainly one way to go about it, but not very practical for when it’s cold out, especially in Wisconsin. Then again, because the pants are so square-shaped and loose, you don’t want to pair them with great big boots that are too clunky or you’ll just look bulked up. So! There are two directions to try: Add in a bit of a winter-friendly heel so you don’t look too stout via wedge-y platform boots or closed-toe heels (seriously, this open-toe on winter shoes trend has got to stop) that you wear with tights underneath. Another fun way to rock the boy jeans is to go with sturdy masculine shoes, like oxfords (I love these because of the pop of color) or comfy mocs with thick wool socks. Pair with a slouchy cardigan or pea coat on top and you’ll look super cute and, more importantly, warm. Thanks for writing Meghan!

  1. We Who See Wedge Bootie, $78, Urban Outfitters
  2. Crocodile Cut Out Booties, $29.99, Charlotte Russe
  3. BDG Saddle Oxford, $48, Urban Outfitters
  4. Miss Me Women’s Kate-3 Mocassin Flat, $29.95, Endless Shoes

Have a fashion or beauty dilemma on your hands? Email your queries to [email protected] with the subject line “Style 911” and we’ll do our best to help sort you out.