How to Wear Flare Jeans Through All Seasons

If you’re wondering how to style flare jeans with different shoes for every season, this guide is for you. In this post, I’m showing how to wear one pair of flare jeans year-round, with outfit ideas for spring, summer, fall, and winter. Check out my previous posts with outfit ideas for all seasons by denim fit: wide-leg jeans | barrel-leg jeans.

Affiliate links are included in this post.

How to Wear Flare Jeans Through All Seasons

My Sizing: I’m 4’10”, and my bust, waist, and hip measurements are 32″, 24″, and 36″. My inseam is 25″ (the measurement from the inside of my leg to my ankle bone). The clothes shown are unaltered and show how they fit me right from the store. I list my sizing beside each item to help you compare when shopping online. When referencing my true size, that is often the smallest option available at a brand or petite xxs/00/24. I wear a size 5 shoe.

My goal with this post is to share outfit ideas and show how different styles of jeans pair with shoes and layers throughout the seasons, so you can find the looks that work best for you.

J.Crew Charley Kickout Cropped Jean

Size Wearing: 24 Classic in Rinse
Fit: true to size – they’re snug at my hips and thighs, but loose in the waist, so a size up wouldn’t work
Inseam: 27.5″ in classic | 25.5″ in petite
Rise: 11.5 ” in classic | 10.5″ in petite
Fabric & Care: 99% cotton/1% Lycra® spandex | machine washable

The Charley Kickout Cropped Jeans from J.Crew feature a high rise, a slim fit through the hips and thighs, and a medium flare leg. I own them in both petite and classic sizing. The petite version has a 25.5″ inseam and hits right at the top of my foot, while the classic version has a 27.5″ inseam and works perfectly as a full-length flare with flats. The jeans are made from 99% cotton and 1% spandex, so they have very little stretch. On me, they fit snug through the hips and thighs but leave some extra room at the waist. Over time, they loosen slightly, making them more comfortable in the thighs while still staying up despite the looser waist. I recommend going with your true size in this style. You can see the petite version styled in this post.