8 Shoes and Boots to Pair with Flare Jeans & Bell Bottoms for Fall and Winter

Flare jeans are making a big comeback this season, and finding the right footwear to complement them can elevate your entire look. Whether you’re rocking slightly bootcut jeans or full-on bell bottoms, the right pair of shoes can transform your outfit. Here’s a guide to the best shoes and boots to wear with flare jeans this fall and winter.

1. Ankle Boots: The Perfect Match for Flare Jeans

Ankle boots are a top choice when it comes to pairing with flare jeans or bell bottoms. With their higher vamp, square toe, and block heels, ankle boots add balance to the wider silhouette of flare jeans. This creates a stylish and cohesive look that works from fall to spring. The key is to ensure that your ankle boots have a snug fit, with the hem of your jeans resting neatly on the boot. For cropped flares, aim to have your boots covered by the hem, creating a clean, polished look.

2. Sneakers for a Casual Vibe

For a more relaxed, off-duty style, sneakers are a great way to wear flare jeans. Retro white sneakers, such as Nike Air Force 1s, pair effortlessly with longer flares for a cool, laid-back vibe. If you prefer a bit of height, platform sneakers are an excellent choice, providing both comfort and style. Keep the hem of your jeans just above the sneaker to maintain a streamlined silhouette.

3. Clogs for a Retro Touch

Clogs are a fantastic option for adding a retro flair to your flare jeans. From classic mules to sportier versions, clogs can be paired with any length of flare jeans for a stylish, vintage-inspired look. Flat clogs, like Birkenstock Bostons, work particularly well with cropped flare jeans. If you’re in the mood for something more cozy, try pairing clogs with chunky wool socks for a winter-ready ensemble.

4. Chunky Loafers: A Trendy Yet Comfortable Choice

Chunky loafers have been all the rage for a while now, and they make a great pairing with flare jeans, whether cropped or full-length. A moderate platform of 1 to 2 inches is ideal for balancing out the proportions of flare jeans. However, if you want to go bold with thicker platforms, stick to longer flare jeans to avoid overpowering the look. You can also style loafers with socks, which is a trend that’s gaining popularity this season.

5. Heels to Elevate the Look

If you want to add some height to your flare jeans outfit, pointed-toe pumps or stiletto heels are perfect. These shoes create a sleek, elongated silhouette that complements the shape of flare jeans. Just be mindful of the length of your jeans—make sure the hem doesn’t drag on the ground to avoid tripping. For a subtler option, kitten heels also look great with cropped or ankle-length flare jeans.

6. Chunky Chelsea Boots for Winter

When it comes to winter outfits, chunky Chelsea boots are a must-have for pairing with flare jeans. Their sturdy design and high vamp make them ideal for colder weather while still looking stylish. These boots are particularly suited for ankle-length or longer flare jeans, as their bulk complements the wider hem of the pants. For a fresh twist, try a platform version of Chelsea boots for added height and comfort.

7. Ballet Flats for a Feminine Touch

For a softer, more feminine look, ballet flats are a great option to wear with flare jeans, especially with a squared toe or Mary Jane style. Cropped flare jeans work best with ballet flats, but make sure the hem of your jeans falls right at or just above the shoe to avoid a bulky appearance. While pairing ballet flats with longer flare jeans can be challenging, it’s best to ensure the hem doesn’t drag on the ground, creating a clean and polished look.

8. Western Boots for a Cowgirl Aesthetic

Flare jeans and western boots make a perfect pairing, especially when the boots are ankle or calf-height. The curve of the boot’s heel naturally complements the flare of the jeans, while the pointed or almond toe adds a stylish touch. To keep the look balanced, ensure the hem of your flare jeans is at least half an inch from the ground, allowing the boots to peek through. For a bold western-inspired outfit, pair your jeans and boots with a chambray shirt or a belt that matches the color of your boots.