If you love jeans that make your legs look longer and give you a gorgeous shape, you need to try a pair of flares!

I’ve always had a soft spot for flare jeans. They’re a little more dramatic than bootcut jeans, and when you get the fit right, they can be incredibly flattering. I especially love dressing them up with a beautiful jacket and heels.

But there’s a knack to wearing them. The length has to be right, the flare needs to suit your proportions, and what you wear on top makes a difference.

Today I’m sharing five ways I’ve styled my flare jeans, from casual tees and chunky sweaters to a colorful jacket and heels, along with a few tips to help you wear them over 50 and look modern.

What’s the Difference Between Flare and Bootcut Jeans?

Bootcut jeans widen just slightly below the knee, while flare jeans have a more noticeable bell shape. Both can make your legs look longer, but flares create a curvier, more dramatic silhouette.

If you’re new to flares, try a baby flare with a smaller leg opening. It’s a nice way to ease into the look.

A fuller flare can be especially flattering if you have wider hips because it helps balance your proportions. If you’re straighter through the hips, a fitted flare can create the illusion of more curves.

And if you’re petite, don’t rule them out! Just be careful that the flare isn’t so wide that it overwhelms your frame.

1. Dress Up Dark-Wash Flares with a Colorful Jacket

This is one of my favorite ways to wear flare jeans!

I paired my dark-wash Veronica Beard flares with a bright yellow double-breasted jacket, and I still love this outfit. The dark indigo denim gives the look a dressier feel, while the yellow adds a gorgeous pop of color.

But it’s the shape of the outfit that makes it work.

The jeans are fitted through the hips and thighs before flaring out below the knee. That creates a beautiful hourglass silhouette, especially when you add a jacket with structured shoulders and a defined waist.

A long, boxy blazer wouldn’t give quite the same effect. With a dramatic flare, I prefer a shorter, more shaped jacket that lets you see the waist and keeps the proportions balanced.

You could create a similar look with a tweed jacket, a cropped blazer, or a shaped cardigan jacket.

Pay Attention to the Rise and Length

One reason these jeans are so flattering is their higher rise. It makes your legs appear to start higher up, especially when you wear a shorter top or tuck one in.

That said, the highest rise isn’t always the best. If you’re short-waisted, a mid-rise or moderately high rise may look more balanced.

And the length? That’s a big one with flare jeans!

Full-length flares should fall close to the floor, covering most of your shoes without dragging. Too short, and you lose that long, flowing line. Too long, and the fabric bunches around your feet.

Even at 5’7″, I needed a good heel with these Veronica Beard jeans.

My tip: Decide which shoes you’ll wear before having your flares hemmed. A pair hemmed for heels won’t necessarily work with flats.

2. Keep It Casual with a Striped Tee

Flare jeans don’t have to be dressy. For a more relaxed look, I paired my Ann Taylor flares with a striped three-quarter-sleeve tee.

I love the sporty feel of stripes with denim. It’s a simple combination, but the flare gives it more personality than an ordinary pair of straight-leg jeans.

The key is the fit of the tee. A top that gently follows your shape works nicely with the wider leg because it keeps the outfit from looking too bulky.

If you don’t like tucking in your tops, look for a tee that ends around your upper hip rather than halfway down your thighs. That way, you still get some shape without emphasizing your tummy.

This is the kind of outfit I’d wear for a casual lunch, shopping, or running around town.

3. Wear Flare Jeans with a Chunky Sweater

Can you wear a chunky sweater with flare jeans? Absolutely!

You just need to pay a little more attention to proportions because you’ve got volume on both the top and bottom.

I find that a chunky sweater looks best when it doesn’t hang too far down over the hips. A shorter knit lets you see more of the jeans and keeps your legs looking longer.

If your sweater is oversized, try a small front tuck or push up the sleeves to show your wrists. It’s a simple way to make the outfit feel less bulky.

And don’t worry about matching a fitted top to every pair of flares. Sometimes the contrast of a cozy, relaxed sweater with a more fitted jean through the hips and thighs is exactly what makes the outfit interesting.

4. Freshen Things Up with White Flare Jeans

 

 

 

I also have a pair of high-waisted white SPANX flares that I love for warmer weather.

Here I’ve paired them with a navy blouse, gold jewelry, and sandals. Navy and white always looks fresh to me, and the combination has a slightly nautical feel that’s perfect for spring and summer.

Notice how the blouse drapes softly rather than clinging. You don’t need a tight top with flare jeans, but it helps if the fabric isn’t so bulky that it hides your shape completely.

The high waist and full-length flare also create a lovely long leg line.

One thing I always check when shopping for white jeans is the thickness of the denim. You don’t want your underwear or pocket linings showing through. A quick check in natural light can save you from a disappointing purchase!

5. Try Something Different: A Shirtdress over Flares

Here’s a more adventurous way to wear flare jeans!

I tried layering a shirtdress over my white SPANX flares, leaving the lower buttons open so the jeans could peek through.

It’s a fun way to play with proportions, but the belt is what makes this outfit work. It defines my waist and keeps all that extra fabric from overwhelming my shape.

If you want to try this, choose a shirtdress in a lightweight fabric that moves easily. A stiff or heavy dress can create too much bulk over the jeans.

I know this look won’t be for everyone, but fashion should be fun, and I enjoy trying something a little different now and then!

What Shoes Look Best with Flare Jeans?

One of the most common questions about flare jeans is what shoes to wear with them.

For a dressier look, I love block heels or heeled ankle boots. They give you height and help the wider legs hang beautifully.

Wedges are another pretty choice, especially with white flares in summer.

For casual outfits, sneakers or pointed-toe flats can work beautifully with a more subtle flare, provided the jeans are the right length.

The most important thing isn’t whether you’re wearing heels or flats. It’s making sure the hem works with your shoes. You want the flare to fall smoothly, not puddle around your feet.

How to Wear Flare Jeans Without Looking Dated

Flare jeans have a definite seventies influence, and that’s part of their charm. But I wouldn’t pile on too many retro pieces at once.

Bell-bottoms, a peasant blouse, fringe, platforms, and a floppy hat? That’s a lot of seventies in one outfit!

Instead, I like mixing flares with simpler, more current pieces, like a striped tee, a beautiful jacket, or a cozy sweater.

I also find that clean denim washes are easier to dress up. Dark indigo looks especially classy, while medium blue and white are lovely for casual outfits.

And remember, you don’t need the widest flare in the store. A subtle flare can be just as flattering and often easier to wear.

Final Thoughts

If you’ve been thinking about trying flare jeans, I say go for it! Start with a pair that fits nicely through the hips and thighs, get the length right, and experiment with different tops until you find a combination you love.

As you can see, flares can go from casual to dressy simply by changing what you wear with them. That’s one of the things I love most about them.

What about you? Are you wearing flare jeans these days, or are you more of a straight-leg or bootcut jeans gal? I’d love to hear!