Boyfriend jeans are often worn rolled at the hem, which shortens their length and showcases a little ankle skin when you wear them with booties. More skin is exposed when you sit down. Here are great examples of the look.

Citizens of Humanity Premium Emerson Distressed JeansPaige Denim Jimmy Jimmy Jeans with Patches

AG Adriano Goldschmied The Beau Slouchy Skinny JeansRag & Bone/JEAN The Dre Skinny Boyfriend Jeans

I don’t want my socks to be visible when I wear my boyfriend jeans this way. Unless I go bare feet, which I do when it’s sufficiently warm, I have three options:

  1. Nude Knee-Highs: I love wearing nude knee-highs because they keep my lower leg warm and comfortable in mild Autumn, Winter and Spring weather. Sometimes I’ll wear full length nude hose to stay extra warm under my jeans. 
  2. Footies: These are trickier because they can slide off your feet as you stride. I wear children’s size footies to create a snug fit. I might try Calvin Klein’s ballet liner sock because the criss-cross straps should keep the footie in place. 
  3. No-Show Ankle Socks: Finding socks that are sufficiently short on the ankle so that your booties cover them works quite well. Extremely short knee-highs that look like no-show ankle socks are another way go. 

Although I don’t personally want to showcase my socks with this look, doing so can be a fashion statement in itself. The scrunched socks peaking out from under the booties remind me of leg warmers. Fun, cuddly and fabulously ’80s. A low contrast between the booties and the socks is the safe way to go, but higher contrast options can be fun too. The visual effect is very casual and probably not the best idea if you’re after a dressier vibe. 

Of course, sometimes the rolls of the jeans are low enough (or the shafts of the booties high enough) that the socks are covered when standing and mostly covered when seated. In this case the choice of socks is more about comfort than anything else.

I have focused on boyfriend jeans, but these options apply to any ankle pant and bootie combinations that expose your leg. If you have sock style recommendations for this look, please share them in the comments below.