Ruth: Hello Stylebook fashion gurus! I’m having some fashion anxiety that I hope you can alleviate. My issue is related to my allegiance to cuffed or cropped boyfriend jeans and how that’s going to work when it comes to shoe choices as the weather gets colder. I always see boyfriend jeans worn with a bit of bare ankle showing below the hem (usually rolled) of the jeans, but what are we supposed to do when it gets too cold for that? Is wearing cozy socks with our ankle boots acceptable? Or will we have to put our beloved boyfriend jeans away until spring? Thank you for any advice you can offer.
Christen, The Shoe Hive: I had to put some serious thought into how to answer this question. Ultimately, the answer is: Yes, you can wear cozy socks with ankle boots. But the kind of sock and how you wear it depend entirely on the type of boyfriend jean in question. Because not all boyfriend jeans are created equal. If you boyfriend jeans are at all tapered near the ankle, I recommend wear a higher, chunkier sock. Tuck your boyfriend jeans into the sock and scrunch the sock atop your ankle boots. This is admittedly, however, a very trendy, country-meets-city look that not everyone will want to attempt.
If that is the case, I suggest investing in thin cashmere socks in a variety of neutrals this year. Wear them with your ankle boots and under your rolled boyfriend jeans. As long as you put thought into the color of the sock and the boot in question, I think you’ll find that you can recreate a very similar look to that with which you have become accustomed.
Finally, I recommend broadening your silhouette range as well. Consider swapping your boyfriend jeans for a skinny jean. It’ll do all of the above, but with much more ease than a boyfriend style. I know skinnies aren’t for everyone, but I also know that despite my love of the boyfriend, my favorite pairs get a lot less wear in fall and winter.