Flare jeans are the new old thing, and you need outfit ideas! What to wear with your flair jeans to bring them into this decade in a style that is all your own.

I know… We’ve all heard the conversation over a hundred times. No more skinnies. So… Wondering what to wear with these bell bottom looking jeans?

Three examples of what to wear with flare jeans

I work for a denim brand and it’s truly fascinating to see the denim trends go in and out throughout the years, and even the months.

We all know skinnies aren’t your best bet for a go-to daily outfit, rather, we’re reaching for something wider or more flared.

Having a hard time visualizing yourself wearing the same jeans you wore in 2008 is typical, no matter where you were in life at the time. This is a tough feat, but I’m here to bring you all of the inspiration and outfit ideas that you need to make it a better trend this time around.

Maybe the fit and flare is a little too much if you’re super over the skinny fit in the thighs, but these tips for how to wear wide leg jeans will do just the trick.

Four different styles of shoes to wear with flare jeans


Personally, I tend to spend the most time picking and choosing the right shoes to go with a new pair of jeans and finding the right ones to wear with flare jeans was a challenge… They really make or break your outfit, for sure!

1. Pointed Toe Pump

It doesn’t have to be a monochrome outfit of course, but a pointed toe pump is too great for a flare jean.

2. White Sneaker

White sneakers will always be the move for an easy outfit.

3. Platform

Remember these bad boys from the 2000’s? I sure do!

4. Loafers

Throw on the trusty loafers and call it a day!

What kinds of shirts to wear with flare jeans


There’s a variety of different tops you can wear to complete the cutest looks with a pair of flares, and it all depends on season and occasion. I’m giving you some of my favorite examples of how to wear them in any and all scenarios to rock the look.

5. Bodysuits

Keep it retro!

6. Graphic Tees

Easy graphic tees with cool accessories pull together the vibe of a flare jean and make it part of the style.

7. Classic Sweater

A classy and classic sweater can turn any pants into something cool and aesthetic.

8. Loose Button Down

Something cropped and tucked is too cute with flares!

9. Sheer Knit

This one needs no explanation… It’s just too cute!

A girl wearing a cropped puffer jacket and flare jeans


Jackets are tricky to figure out how to wear with flare jeans or any jeans, no doubt.

Layers can be so fun but if it doesn’t come naturally or if you don’t know exactly what works together, you need some inspiration photos, ASAP!

10. Cropped Puffer

A cropped puffer balances out the volume up top and bottom.

11. Trench Coats

The slender trench coat with a cool flare kicking out at the bottom is a really cute silhouette that I adore.

12. Trendy Teddy

Grab your favorite teddy in a trendy color or pattern for this dreamy comfy look.

13. Extreme Lapel Leather

Again, it’s all about balancing the volume, so adding it back up top keeps it all evened out.

Flare jeans at Free People

Free People Inspo

The brand Free People has totally mastered this look of what to wear with flare jeans. The style they put together is right up my personal style alley and I would love to recreate every outfit from their website.

14. Bandana Top

A slouchy jeans with a tiny top is so cute, fun, and flirty.

15. Statement Jeans

The statement jeans with a lounge sweater is the dreamiest cool-girl outfit.

16.Extreme Flares

Everything about this look. All of it. I’m obsessed with all of it.

17. Crop Top And Bomber

A crop and bomber combo makes this vintage look ultra cool. Bomber jackets go in and out of style, but right now they’re hot in a more retro than modern way, perfect for a flare jean.

Especially when it comes to a more free spirit and hippie-styled outfits, this is the place to get the look.

Flare Jeans Vs. Bootcut

In my high school years, there were two similar styles we were rocking, the flares and the bootcut.

They’re pretty similar to each other in reality, and there are some different variations of both, but ultimately, the flare jeans are simply a bigger flare. That’s all there is to it. Really!

I do own some boot cuts that have more of a looser fit through the thighs, and all throughout the jean, but that’s not a specific characteristic of a boot cut. Just a possibility!

Flare Jeans In 2024

Yes, flares are cool again in 2024. And I know some of you are cringing, but it’s okay!

If you’re here, you’re already diving into elevating these looks and turning them into something you would want to wear today. And I support you in that.

So grab your old flare jeans if you still have them or get shopping for a fresh pair and jump back in on this flare jean train!

Flare jeans are so reminiscent of the 70’s trends we always tend to keep in our back pocket.

A girl wearing booties and flare jeans

This is one of my favorite eras of fashion. The jeans, the fabrics, the patterns, the loose fits… And bringing back the 2000’s flare jean is the 2024 version of bringing back the 70’s like we did in Y2K.

Have fun with these styles, they’re so specific to the jean you’re wearing and how it fits you, rather than just the same old top you wear about every day. Though I love those too.

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