I didn’t actually warm up to wearing flares again (not since my junior high/high school days) until I saw some pictures on Pinterest of flares being styled in ways that looked a lot more modern and less 70s. I then bought a pair of flares and wore them, and immediately remembered why I still prefer skinnies. At 5’1, I have to make some kind of hemming alteration to flares, no matter what. If I find a pair I love but they have a 35-inch inseam, the jeans will lose their flare and the cut will change if I get them hemmed. So flares have to be just the right length or not much longer if I want to keep the cut the same. And, I have to have specific pairs to wear with different heel heights. Ugh, the struggle.
If you’re up for the struggle, or if you are of normal height–this is my favorite way to style flares. It looks effortless, chic, and a little undone. The oversize sweater makes this look cozy and perfect for fall, and adding a flare jean dresses up the look (and gives a different feel than a pair of skinny jeans would–though skinny jeans are equally great to wear with an oversize sweater). While high-school me would wear flares with torn-up Converse sneakers and would let the back hems of my flare jeans drag and rip as I walked all over them, current me only prefers flares with heels. Heels really are the best shoe to wear with flares–the combination makes your legs look like they go on for days. I’m honestly not a huge fan of wearing flares with any kind of flat shoe–if you’re wearing flats, a skinny, boyfriend, straight, or girlfriend jean is the way to go. So, pair your flares with a nice heeled boot or stiletto–or a marriage of the two, like this Louboutin pair. Add a bag that’s a little less structured and more utilitarian, like this leather messenger, and complete the look with my favorite accessory: a ring that looks like glamorous brass knuckles.