Cool combinations to wear year-round.
By Danielle Naer | Last Updated Nov 20, 2025
The masses are split on flare jeans. They have their benefits—they're just the right amount of retro, for example conjuring images of Jane Birkin wearing them with verve back when. That said, they’re also famously hard to style. Knowing what shoes to wear with flare jeans is the closest thing to rocket science that we have in the fashion world—so we decided to do a case study on the tricky silhouette.
First thing to consider: the length of your flare jean. Longer silhouettes will warrant a heeled ankle boot, forming that floor-grazing halo around the shaft of the boot. If you're enlisting a cropped flare jean, you can take more liberties, tying in clogs, ballerinas, and other flat shoe styles. Before you dive in, peruse our edit of stylish flare jeans to shop now—and begin your styling journey from there.
From Desk to Drinks: Long Flare Jeans and Ankle Boots
First up, our editors' favorite shoes to wear with flare jeans: ankle boots. Whether trad or split-hemmed, these pants work great with booties of all sorts. Try something with a flat, pointed toe like a sculpted almond-toe silhouette. This is your go-to combo for dinner dates and Fridays at the office.
Elizée – Sabina Bootie
Made in Italy in smooth black calf leather, Sabina is a polished ankle boot with a sculpted almond toe and a slim block heel that works seamlessly with long flare jeans. The subtle chain detail adds a modern accent without overpowering the look, making it a strong choice for office days and dinner plans.
Elizée – Cora Bootie
Cora is an Italian-made bootie in a warm brown leather that complements the ease of flare denim. The almond toe and slim block heel create a clean, lengthened line, while the curved front panel and tonal buckle bring soft structure. It pairs well with both tailored layers and relaxed weekend outfits.
For Elevated Everyday Wear: Cropped Flare Jeans and Ballet Flats
Looking to style a pair of cropped flare jeans? Ballet flats are your answer. Not only is the shoe trending for spring and summer, it's also as timeless as they come. Style a pair of wide-leg jeans with a polished flat for Sunday strolls and days shopping around SoHo.
Elizée – Gemma Flat
Gemma is an Italian-designed flat with a soft almond toe and subtle pearl-like accents that complement cropped flare jeans. The lightweight construction and cushioned interior make it an easy choice for days on the go, while the streamlined shape adds a polished touch to everyday looks.
For Special Occasions With Long Flare Jeans: Slingbacks
As for what to wear with flare jeans while perambulating around museums or sipping Sancerre, slingbacks are your answer. Pair your best cropped jeans with a delicate kitten heel for a dressed-up feel.
Elizée – Portia Slingback
Portia is an Italian-made slingback with a pointed toe and a sculpted kitten heel that works seamlessly with long flare jeans. The smooth leather and triple-layered comfort insole give it an easy, wearable lift for gallery visits, dinners, and dressed-up days when you want a sleek finishing touch.
We invite you to read the full article on Editorialist.