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What to Wear with Flare Jeans—10 Stylish Outfit Ideas

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I recently bought a pair of flare jeans after seeing them more and more. After swearing them off in lieu of skinny jeans for many years, it felt a little weird to wear a wider leg again, but the flared jeans (and wide leg jeans) have really grown on me and I know that they’ll be a pair I reach for a ton this fall and winter. I love that flared jeans give you more shape and curve than straight leg jeans and look great with so many different outfits.

how to style flare jeans

I’ve been playing around with styling them and there are endless possibilities on how to style these cute and versatile jeans. Let’s dive into some outfit inspiration that you can wear year round.

Are Flare Jeans Back In Style?

Flare jeans have made a stylish comeback, with a modern twist. The waists are much higher than what I remember wearing back in high school and you’ll find them in long lengths and cropped lengths.

You’ll even find different bell or flare sizes on them. Personally, I like the jeans that aren’t overly exaggerated and just have a nice, more subtle flare to them. To me, this is more classic and will last longer in your wardrobe than a trendier pair.

While of course a blue pair in a classic denim wash is a fave, a dark wash looks nice, and a black wash is always a good staple for colder months, while white denim is so crisp and cool for supring and summer..

What to Wear with Flare Jeans

At the end of the day, you can wear just about anything with flare jeans like you can with regular jeans, but here are a few questions I asked myself when I first got them, and I’m guessing you might have the same ones!

What Shoes to Wear with Flare Jeans

This was my number one question when I bought them, but it turns out flare jeans can be paired with a wide variety of shoes for bunch of different looks.

Ballet flats offer a chic and feminine look. They’re casual and are having a moment right now. You have your classic ones, mesh ones and Mary Jane ballet flats to choose from. Skip and overly rounded toe and opt for a slightly squared toe for a modern look. A par of flats is always comfortable too!

Booties or heeled boots that hit at the ankle are a classic and so great for fall and winter. I love a pointed toe bootie that lengthens and elongates the leg.

Clogs provide a retro and bohemian vibe, while mules offer a sleek and modern touch.

Sneakers give a casual and laid-back feel to the outfit, making flare jeans a versatile and stylish option for any occasion. Ideal for busy days as a mom!

Sandals for warmer months are a perfect match too. Opt for something with a thin strap to not add weight to your bottom half since the leg is already more voluminous at the bottom. You can do a heeled or flat sandal.

What Length Should Flare Jeans Be

The length of flare jeans should ideally be long enough to almost graze the floor when wearing heels and cover the top of your shoes when wearing flats.

You don’t want them to drag on the floor, that’s a quick way to ruin your jeans and have them look less polished. Definitely have them tailored if they’re too long for you. The length ultimately depends on the type of shoes you choose to wear with them.

What Body Types are Best for Flare Jeans

Flare jeans are versatile and can be flattering on all body types—I’m a. believer in wearing what makes you feel confident, no matter what your body type is.

A higher rise or high waist style does a great job of elongating the legs and defining the waist. Pair heels if you’re shorter to make your legs look longer, if you want.

How to Style Flare Jeans—10 Outfit Ideas

There are so many ways to style flare jeans, so let’s go through some different outfit ideas so you can get inspired to wear your flared jeans a bunch of different ways whether you’ve got standard blue or black flare jeans, you can wear these so many different ways.

Casual Sweater Look

what to wear with flare jeans

This is such an easy, go-to outfit for fall and winter. Pair a cozy sweater and ankle boots and call it a day! This is a classic look and easy way to wear your jeans. You can also pair this outfit with flat shoes, which are always comfortable. Try ballet flats, slides, loafers and more—just make sure your jeans aren’t too long and bunching up at the bottom.

Business Casual

what to wear with flare jeans

Pair a classy v-neck cashmere sweater with an oversized coat and pointed ankle boots for a looks that’s casual, but appropriate for any casual offices. I paired navy on navy here and threw on a fun printed boot to add something extra, but if snakeskin doesn’t feel right, opt for a clean and crisp black boot.

what to wear with flare jeans

Floral Top & Clogs

how to style flare jeans

I love the boho combination of a flowy floral blouses paired with clogs and flared jeans. Add some hoop earrings and a leather bag to complete the look.

Add a Pop of Red

what to wear with flare jeans

When in doubt, adding a touch of red always makes an outfit more interesting and unexpected. I love pairing it with a pair of red shoes which always feels warm and fun for the fall and winter seasons. Choose from fabrics like suede or velvet to add some warmth to your look.

T-Shirt & Sneakers

how to style flare jeans

Throw on your favorite white t-shirt and a baseball hat for an easy casual look. If you’re planning on wearing your flare jeans with flats more than heels, it may be worth having them altered for length as you can see mine are a little bunched at the bottom.

Ankle Boots & a Blazer

how to style flare jeans

A pair of black strappy heels is the perfect classic combination. I love throwing on an oversized blazer for a cool, sophisticated look. I would wear this for dinner, or lunch with friends, or even to the office.

Tank Top & Quilted Jacket

what to wear with flare jeans

Dress up a silky tank with a fun quilted jacket as the days get cooler. If your feet are chilly, swap for brown ankle booties for a cool fall look.

Denim on Denim

what to wear with flare jeans

Denim on denim is always such a classic look. I love throwing on an oversized coat for fall which dresses up this casual combination. You can wear denim that’s the same shade, or mix and match like I did here.

These flare jeans are quickly becoming one of my favorite styles of jeans and while I loved my skinny jeans for a long time, I am loving that wider leg jeans and flares are back in style as it adds more interest to my closet. These are going to be on repeat for fall and winter because they pair so perfectly with ankle boots! Will you give them a try?

BTW, what to wear with green pants, and what to wear with black pants.

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