What Shoes to Wear with Flare Jeans

Peek-a-Boo Pumps

With longer jeans—and especially flares—you're often covering more of the foot, so a pointed pump offers a great way to ensure your shoes don't get lost in the shuffle. These pumps from Steve Madden have a high heel for preventing jeans from dragging, and are cut lower on the toes for a peek-a-boo effect. While we consider the black suede a wardrobe staple, it also comes in a spectrum of other colors and finishes (such as crystal rhinestone) for bold impressions.

Shop it: Steve Madden Daisie Pumps

Ankle Boots

Flare jeans are typically roomy enough to accommodate varying boot heights and widths, but we tend to prefer ankle cuts for greater ventilation and range of motion. This pick from Sam Edelman, which has a detailed toe and thick block heel, offers sophistication, stretch (read: comfort), and stability. Part western, part city-slicker, don't be surprised if you find yours all over town and racking up major compliments in the process (there are additional colors and patterns for switching things up).

Shop it: Sam Edelman Winona Western Boot

Platform Heels

There's nothing like a pair of jeans with enough space to support your own mini stage. We're currently loving the ravishingly retro feel of these skyscrapers from Nine West, which have a five-star rating, come in three luxe finishes (the metallic gold is that of our disco dreams), and have the power to command a room—perfect for your next girls' or date night!

Shop it: Nine West Zenna Platform Sandals

Chunky Clogs and Mules

Speaking of retro, clogs and mules are one of the easiest ways to achieve an effortlessly-chic '70s look. This pick from Madewell, beloved by reviewers for its simple, yet stylish craftsmanship, combines luxe leather with natural wood and has an open toe for more breathability.

Shop it: Madewell The Evelyn Slide Clog

Padded and Wedged Sandals

Foambed sandals are having a moment (and we hope it continues, because we could use the extra support). This new pair from Birdies—available in several shades, as well as cheetah—has thick criss-cross straps for adding another element of design to your look without having to worry about your jeans getting caught up in cutouts.

Shop it: Birdies The Robin Sandal

For Cropped Flare Jeans

Kitten Pumps and Mules

When it comes to cropped flares, the trick is to complete, not compete. We love the beautiful, yet still subtle knot accent on these limited-edition metallic sandals from J.Crew, which sit somewhere between a slide and an open-toe mule and go with just about everything (while the jeans don't warrant it, the short heel also adds an elevated touch).

Shop it: J.Crew Knotted Block-Heel Sandals in Metallic Leather

Mid-Calf Boots

We love mid-calf boots for bridging the gap between cropped flares and the foot on cooler days. This stretchy knit from Everlane, which has a near five-star rating and is made of 88 percent recycled polyester, offers a breathable, snug fit that won't interfere with your flare, and will save you during seasonal transitions.

Shop it: Everlane The Glove Boot

Ankle-Strap Sandals

Make the most of your cropped real estate with a strappy flat or heeled sandal. This block style from Marc Fisher, which comes in four snakeskin finishes, goes with a variety of washes and makes the everyday feel like a getaway.

Shop it: Marc Fischer Jacinda Block Heel Strappy Sandal

Ballets and Loafers

Add a refined touch to your cropped flare with a sophisticated ballet flat or loafer. An exposed foot and ankle are prime for showing off little details like the dainty bow on this best-selling pair from Aerosoles, which prioritizes comfort and spans across fourteen colors and patterns.

Shop it: Aerosoles Homerun Ballet Flats

Slip-ons and Sneakers

When it comes to stylish, comfortable shoes that'll never slow you down, slip-ons and sneakers are difficult to top. Since they're typically less bulky than other options, they're great to pair underneath a cropped flare. We recommend Veja's kicks, which have garnered a following for their comfortability and versatility.

Shop it: Veja Esplar Low-Top Sneakers