Wearing booties with boyfriend jeans and relaxed skinnies is a great look for Spring, Autumn, and a mild Winter. Rolling the hems to give the outfit structure and interest is part of the boyfriend jeans charm, but it also shortens the inseam. If you wear shorter booties with boyfriend jeans, you’ll showcase lower leg skin between the hem of the jeans and the tops of the booties. This is one way to wear the combination, but it’s not the only way. 

I’ve found that I prefer to wear booties that are slightly taller in the shaft with boyfriend jeans, as you can see here. That way I can wear the combination for longer without feeling cold. When sporting this combination I wear nude knee-highs for a faux bare-legged effect, or short invisible ankle socks (I don’t like my socks to be visible when I’m seated). 

Just to be crystal clear about what I mean by a shorter and taller shaft, here are visuals. The first two booties have a short shaft, while the second two have a taller shaft.

Unfortunately, booties that are a little taller in the shaft can be less comfortable than their shorter cousins because the front edge cuts into your shins as you stride. I’ve found that choosing styles made of soft leather with elasticated side inserts increases the comfort of the taller bootie. Also, I’ve occasionally popped a bit of moleskin on the inside of the tops of the vamps to prevent shin rubbing. 

If you like the look and comfort of an ankle bootie, don’t overlook this simple way of getting more mileage from your boyfriend jeans.