How to Wear Flare Jeans Over 50
Flare jeans are one of those timeless styles that flatter so many body types. When styled right, they create long, lean lines and bring a little drama (in the best way!) to your outfit. And trust me, they don’t have to look like something you wore in high school. You just need a few tricks to make them feel modern, flattering, and completely wearable at any age. Today, I’m sharing how to wear flare jeans, which tops and shoes pair best, and some of my favorite flare jeans that work beautifully for women over 50!
What to Look for in Flare Jeans Over 50
Not all flares are created equal, and if it’s been a while since you wore a pair, here are a few things I recommend looking for:
- A Mid or High Rise:
Skip anything low-rise. A higher rise gives you more tummy coverage and smooths everything out, especially if you’re wearing a tucked-in or shorter top. - Some Stretch:
A little bit of spandex goes a long way. Look for jeans with at least 1–2% elastane so you can move comfortably without feeling stiff or restricted. - A Slim Fit Through the Thigh:
You want the jeans to skim your thigh and then flare out gently from the knee. This helps keep the shape flattering and elongating. - A Dark or Medium Wash:
Dark denim is slimming and easy to dress up or down. But don’t shy away from a faded flare—just pair it with a more polished top or structured jacket to keep the look elevated.
How to Style Flare Jeans in Your 50s
You don’t have to reinvent your wardrobe to make flare jeans work. Here are a few outfit ideas that always look stylish—and age-appropriate.
1. Flare Jeans + Fitted Top + Wedges or Block Heels
This is a simple go-to flare jeans outfit for summer. A fitted knit top or blouse tucked in gives you shape and keeps your proportions balanced. Add a pair of wedges or block-heel sandals to show off that flare and give your legs a boost.
2. Flare Jeans + Button-Up Shirt + Flats
This is such a classic look. I love pairing flare jeans with a white button-up or a chambray shirt. Add a belt to define your waist and finish the look with flats or loafers.
4. Flare Jeans + Flowy Top
A floaty boho-style blouse works beautifully with flare jeans, especially if you’re going for a relaxed weekend vibe. Just be mindful of volume—if the top is flowy, make sure the jeans are more tailored through the hips and thighs.
The Best Shoes to Wear with Flare Jeans
Shoes can make or break a flare jean outfit. Since flares are longer and wider at the hem, you’ll want to make sure your shoes give you a little lift or keep your legs looking long.
Wedges:
Probably my number one pick! They give you height and balance the flare perfectly. I also love wearing block heels with my flare jeans, too!
Heeled Booties:
These are great in fall and winter, especially with a pointed toe that peeks out under the hem!
Sneakers:
If you’re aiming for casual comfort, these can work—just make sure the flare isn’t dragging on the ground. Try a platform style sneaker so you aren’t stepping on your pants!
Mules or Loafers:
This is one of my go-to shoes for a more dressed-up look that’s still comfortable!
Always check your jean length. The hem should just graze the top of your foot or shoe—not puddle on the floor. If you’re petite, look for a cropped flare or buy a regular pair and have them hemmed.
Want more tips for styling and purchasing jeans? Read:
Can You Wear Flare Jeans with Flats?
Technically, yes—but it can be tricky. A very slight flare or kick flare works best with flats. Traditional flares usually need a heel to keep the proportions right. If you do go flat, try a pointy-toe style to help elongate your leg line.
What’s the Difference Between Flare and Bootcut Jeans?
This is a question I get a lot, and it’s a good one—especially since the lines can be a little blurry depending on the brand.
Flare jeans have a more dramatic shape. They’re fitted through the thigh and start to widen from the knee down, creating that full “flare” effect. Think a little more retro, a little more fashion-forward.
Bootcut jeans, on the other hand, have a more subtle leg opening. They’re designed to just fit over a boot, so the flare is much gentler and often easier to style for everyday. If you’re new to wider-leg denim, bootcut is a great starting point.
The Best Flare Jeans for Women Over 50
These LOFT flare jeans have a nice faded medium wash that is perfect for an everyday jean! The relaxed fit through the hip and thigh makes them comfy, and the high rise gives you great tummy coverage.
Sofia Vergara’s line at Walmart always surprises me in the best way! These flares hug your curves in all the right places, and the high rise smooths everything out up top. They look designer, but the price tag says otherwise at under $25!
If you love comfort but still want that flare silhouette, this pull-on pair is a dream. No buttons or zippers to fuss with—just smooth stretch denim with a flattering flare. These would be great for a day of travel!
Old Navy calls these “Wow” jeans, and honestly, that’s pretty accurate. These are a great budget-friendly option with a nice high rise and a clean flare leg. The stretch makes them super comfortable for all-day wear, and they come in a wide range of washes!
If you want a dramatic flare with a little polish, the Mia Palazzo is a showstopper. These feel like a mix between trouser jeans and flares, and they’re perfect for dressing up. Like all NYDJ styles, they have the slimming fit built in that smooths and shapes your belly and booty!
These look like jeans but feel like leggings—in the best way. SPANX added shaping technology that holds you in without feeling tight, and the flare gives your legs a nice long look. These are the kind of jeans you’ll reach for when you want to look pulled together and feel comfortable.
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I have a pair of Sofia jeans and love them. Would love to try the Spanx white jeans.
I couldn’t agree more with all your advice for wearing flares. Now, I am off to get a new pair of them!!
🙂 found it took 4 tries.
I love the eyelet long sleeve button up – stunning with those white pants,
🙂 Found it. Wish I had your nice long legs to wear flair pants. They look lovely on you!!!