What Shoes to Wear with Flare Jeans (And What to Avoid)

I’m so thankful that flare jeans are a big trend this year. They’re a refreshing alternative to skinny or straight-leg styles (I always feel more polished in a pretty pair of flare jeans). While they’re practical and appropriate for many settings, pairing the right shoes with them is important. It can make all the difference between a flattering, cohesive look and one that feels mismatched. Here’s your ultimate guide to the best shoe styles for flare jeans and what to avoid, including tips for cropped and ankle-length flares, like the super popular “kick flare” jeans.

The Best Shoe Styles for Flared Jeans

Flare jeans create a wide-leg silhouette that’s versatile but specific when it comes to footwear. Choosing the right shoes is all about balancing proportions, elongating your legs, and matching the vibe of your outfit. The pair of flare jeans I’m wearing below is the Abercrombie Ultra High Rise Stretch Flare Jean. They are from two years ago, so the exact wash is almost sold out, but Abercrombie now has a High Rise Vintage Flare Jean (also in a comfort stretch denim that I LOVE). That’s what I’d order now. I wear a size 25 in my pair.

Here are my tips!

How to Style Loafers with Flare Jeans

Loafers are a classic choice that pairs surprisingly well with flare jeans. Their sleek design complements the polished, retro feel of flared denim. Loafers also ensure that your outfit is appropriate and polished for a casual workplace. This Corrine-style lug sole loafer from Madewell is my favorite pair to style with flare jeans. Unfortunately, brown was last year’s colorway! Zappos carries a few leftover sizes in the brown, so be sure to check there.

How to style: Choose heeled or lug sole loafers to add height and elongate the legs, or stick with flat loafers for a casual, preppy vibe. I find that loafers with a thicker sole look best, especially since I’m petite; height always helps elongate my legs.

Best Fit: Full-length flares that skim the ground look incredibly chic with loafers. You can also easily style kick-flare jeans with loafers. Kick flare jeans work with almost all styles of shoes since the point is to show the shoe in its entirety.

How to Style Platform Shoes with Flare Jeans

Platform shoes naturally match flared jeans, creating a harmonious retro vibe. Platforms add height without sacrificing comfort and echo the 70s style often associated with flares. They also elongate the leg of the pants, which is the most flattering part of flare jeans. 

My favorite platform shoes are a pair of dressy heels from Loeffler Randall. I wear them most often with dresses since they’re on the dressy side, but they also look amazing with flare jeans. I opt for a leather or rattan platform heel in the warmer months. The pair I’ve styled in the photos below are the Lacye Heels by Dolce Vita. They’re almost sold out since they were last year’s style, but you can find a few sizes available. I feel sure they’ll make a similar pair again this spring.

How to Style: Pair suede or leather platforms with high-waisted flare jeans for a throwback-inspired outfit.

Best Fit: Full-length flares with a slightly longer hem are ideal, as platforms help prevent the hem from dragging. I love that my flare jeans graze the ground when I barely wear platform shoes. 

How to Style High Heels with Flare Jeans

Heels are one of the easiest ways to make flare jeans look elegant and leg-lengthening. They lift the silhouette and create a sleek, elongated look. A pump works best when dressing my flare jeans up for a work look. While jeans aren’t always appropriate in a workplace, if denim is allowed in your office, opt for a dark wash and a pair of flattering pumps.

How to Style: Pointed-toe heels peek beautifully out from underneath flare jeans, while block heels add stability. I like both! For comfort, a block heel may be your best friend (especially this Zala block heel). However, if you are comfortable with a stiletto-style heel, I always think they’re the most flattering and chic option. This pair of brown suede pumps from Nine West is similar to the pair I’m wearing in the photos below. Mine are years old!

Best Fit: Choose heels with full-length flares for a sophisticated, streamlined finish. Again, make sure the hem of your jeans covers the majority of the shoe and almost hits the ground. 

How to Style Ankle Boots with Flare Jeans

Ankle boots are a stylish and practical choice for flare jeans. The proper ankle boots add height and polish without overpowering the wide-leg silhouette. In the winter, I wear ankle boots almost whenever I leave the house. Not only are they generally warm and comfortable, they’re also a fashionable choice with nearly any outfit. My favorite pair of ankle boots is this Downtown Boot by Margaux in Chocolate Brown. They’re splurge-y, but I wear them so often that it totally justifies the cost.

How to Style: Pointed-toe or slim-heeled ankle boots work best, as they slip neatly under the hem. Avoid overly chunky styles, which can clash with the flared shape.

Best Fit: Full-length or ankle-length flares work particularly well with ankle boots. Kick flare jeans can work with ankle boots as long as the boot and hem of the jeans overlap just a smidge. When styling kick-flare jeans with boots, you don’t want your ankle to show as you do for other shoes. Read this post for details on how to style ankle boots with all styles of jeans.

How to Style Sneakers with Flare Jeans

Sneakers are a casual and versatile option for flares, especially cropped styles, like kick-flare jeans. They bring a relaxed vibe to flared jeans, making them ideal for daytime outings. A cute pair of fashion sneakers is my go-to when I’m wearing a casual outfit. I like to be comfortable enough to chase my two boys around while still feeling polished in a real outfit (rather than athleisure). I have a handful of different “fashion sneaker” styles, but I find that a pair of suede or leather option works best with denim. I prefer these Talia sneakers from Sam Edelman or the Recife Vejas.

How to Style: Opt for platform or sleek low-profile sneakers to keep the proportions balanced.

Best Fit: Cropped or ankle-length flares pair best with sneakers, showing off the shoe’s silhouette. However, full-length flare jeans also work well as long as your jeans are hemmed to barely hit the bottom of the shoe without dragging on the ground.

How to Style Clogs with Flare Leg Jeans

Clogs are having a moment, and they pair beautifully with flares for a boho-chic vibe. Their chunky soles balance the wide-leg silhouette while adding height, similar to the platform heels discussed above. You may also find them categorized as “mules ” when shopping for clogs. Both work perfectly with flare jeans, both full-length and kick-flare. The pair of clogs I’m wearing in the photos below is very old, but this Macarro Mule from Madewell is similar.

How to Style: Pair wooden or leather clogs with flared denim for an earthy, 70s-inspired look.

Best Fit: Full-length flares that skim the top of the clog work best.

How to Style High Boots with Flare Jeans

High boots can be a dramatic and stylish pairing with flares in cooler months. Tall boots fit seamlessly under wide-leg jeans, creating a smooth, elongated line. That’s assuming your tall boots aren’t knee-high, of course. Knee-high boots can bulge at the top of the knee underneath flares, but a pair of, say, cowboy boots that hits your mid-calf should be fine.

How to Style: Choose heeled knee-high boots for a sleek, polished look, or go for a chunkier sole for a casual vibe.

Best Fit: Full-length flares that cover the boot opening create a clean silhouette. Be sure your boots don’t bulge under the jeans – if you notice that you can clearly see the shape of the top of your boot under your jeans, opt for a shorter boot.

How to Style Flats and Slides with Flare Jeans

Flats and slides are a great option for warmer weather or casual settings. They keep the look simple and comfortable while maintaining a polished edge. And if you opt for a pointed-toe flat, they look even more polished, perfect for a work setting. The flats I’m wearing in the photos below are a favorite purchase of mine from this past year’s Nordstrom Anniversary Sale. They’re the Landon Pointed Toe Ballet Flat by Stuart Weitzman. Unfortunately, it seems they’re now sold out, but this pair of Quince flats is similar (and I happen to LOVE Quince).

How to Style: Look for pointed-toe flats or structured slides for a chic pairing with cropped or ankle-length flares

Best Fit: Cropped flares or ankle-length styles showcase flats best, as full-length jeans may overwhelm this shoe style.

How to Style Different Fits of Flare Jeans

Cropped or Kick Out Crop Flare Jeans

Cropped flare jeans, which hit above the ankle, require specific styling to avoid cutting off the leg line. My favorite pair of kick-out crop flare jeans are the Lennon High Rise Boot from Pistola. They’re stretchy and flattering, and they hold their shape all day long.

• Best Shoes: Platform sandals, sneakers, or pointed-toe flats are ideal for cropped flares, as they help elongate the legs. Ankle boots work well with cropped flares as well as long as the jean just barely overlaps the top of the boot to cover the ankle.
• Avoid: Chunky boots or overly casual flip-flops, which can clash with the cropped silhouette.

Ankle-Length Flares

Ankle-length flares, slightly longer than cropped styles, work well with a variety of shoes.

• Best Shoes: Ankle boots, sneakers, and heeled sandals are great choices.
• Avoid: Overly chunky shoes or clogs that may disrupt the proportions of the shorter hemline.

What About Crop & Ankle Flares with Sneakers?

Sneakers can work with crop and ankle flares, but proportions are key.

• Low-Profile Sneakers: Sleek, simple sneakers pair well with cropped or ankle-length flares. The pair I’m wearing below are the Talia sneakers from Sam Edelman.
• Platform Sneakers: These are ideal for full-length flares, adding height while balancing the wide-leg silhouette.

Can I Wear Ankle Boots with Flare Jeans?

Yes, ankle boots can look fantastic with flare jeans, but the fit and style matter.

• Pointed-Toe Boots: Slim and sleek ankle boots slip easily under the hem of flares without creating bulk.
• Avoid Chunky Boots: Overly thick or wide ankle boots can clash with the flared silhouette.
• Ideal Hem Length: Full-length flares that graze the top of the boot or slightly cover it create the best look.

What Tops to Wear with Flared Jeans?

The right top can enhance the silhouette of flared jeans and complete your outfit.

• Fitted or Tucked-In Tops: Turtlenecks, fitted tees, or bodysuits pair beautifully with flares, balancing the wide-leg shape. I shared my favorite Tuckernuck blouses in this roundup on the blog.
• Cropped Tops: Pair cropped tops with high-waisted flares for a retro-inspired look.
• Oversized Outerwear: Longline coats, puffers, or blazers can add structure while complementing the dramatic flare. A roundup of the cutest puffer coats is linked here, along with my post on the best winter jackets. I also have a post with 10 ways to style a blazer here.
• Avoid Baggy Tops: Loose or shapeless tops can overwhelm the silhouette of flared jeans, making the outfit look unbalanced.

Final Thoughts

Flare jeans are a versatile and stylish option for anyone looking to switch up their denim game. The key to pulling off this dramatic silhouette is pairing them with the right shoes and tops. From platform sneakers to heeled boots, your choice of footwear can take flared jeans from casual and relaxed to polished and chic. By following these styling tips, you’ll always look put-together and on-trend in your flares.

What are your favorite shoes to wear with flare jeans? Let me know in the comments!

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