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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14 This is the confidence we have in approaching God: that if we ask anything according to his will, he hears us.
😊
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!!!
FOUND IT
🙂
Great information!
Thanks for clarifying what works with what.
I like a good flare jean. I feel like they help balance my hips. 🙂
🙂 Nice selections!
🙂 love the jeans, they don’t look at all like what you might think of pull on pants and jeans!! I’m always looking for a good travel pant and jeans!!
😊 I love all of them. Flare and bootleg are the most flattering on me. They make my short legs look long and I feel tall when I wear them. You’re looking long and lean in them too.
I do like flared jeans the help balance the body.
🙂 Lots of great options!
I need to try a pair of flared jeans…
thank you for all of the suggestions. ☺
Flare jeans look good on you. Found it 🙂
😄. I’m not a fan of flare jeans mainly because I can’t wear heels and as you stated, they don’t look good with flats!!
😊 Most of my jeans are flared. Thanks for the suggestion.
Hi Tania,
I have dark circles (really dark) and I was I was wondering if you have ever come across a product that would hide them without caking?
Laura, the only product that will hide really dark circles is It Cosmetics is Bye Bye Under Eye Cream. You might have to add a smidge of eye cream to it if it tries to crack.
😊 I’ve always preferred a flare. Different width at different points in my life but I’ve always felt they’re the most flattering. Everytime I’m wearing flares I get positive compliments. I do like my slim fit for boots and straight legs once in awhile but love the flares! And so many cute pair here.
☺️. These are all cute outfits.
Stephanie
🙂
Love the light wash jeans from ‘Loft.’
🙂
Great options for flare jeans! I’ve always steered away from them, but I think I’ll give them a try!
🙂 I usually wear a straight leg jeans.
😃 Thank you for sharing what the difference is between bootcut and flare.
🙂
I like flair jeans on other people, but I think boot cut works better for me.
😀 I really appreciate you giving us so any options and at various price points! Thank you!
😊 I prefer straight leg
🙂 Lots of good picks here
😊Lots of good choices! Thanks for all the research.
😁I really like flare jeans but I’m so short and I have a hard time finding ones that fit. I’m going to check out a few pairs you showed today.
😊
Thanks for all the ideas for flare jeans. I usually go for a straight leg jean but these look so good on you I’m gonna check some of these styles out.
Found it :)😀
Love a good pair of flare jeans! Found it! 🙂
😵💫good selection of jeans
🙂 I’m not a big fan of flare jeans but I do like the white ones.
🙂 I love the Spanx and Nordstrom flares. They look so good on you.
😊 I love flare leg jeans. Great selection in this post.
🙂 I am a petite size and the Wow jeans from Old Navy work perfectly for me plus they are inexpensive!
🙂 Thank you for showing flowy top options to pair with flared jeans!
🙂I am a plus-size 16w. I usually wear straight leg jeans. I need to see if I can find a fare leg jean that I can wear. I like dark wash but have worn light wash.
“)I like the look of the crisp white shirt with the dark wash jeans.
FOUND IT🙂! Don’t think I have any flare jeans. When we lived in AZ a few years ago, we had a pool and woke up one spring morning to find a male & female duck swimming in our pool. This continued for a few days and then I noticed the female had laid her eggs in one of my pool pots! The female spent all her days sitting on her eggs and then about 4 weeks later we had fun watching the eggs hatch & watching the babies learn to swim in our pool!
Oh, my! What a cute story!
🙂 I’ve been struggling to find a flare that works. Thanks for the tips
Found it😀 nice options
I love the Tiana in the first picture. It is perfect.
Found it.
🙂 found it. The navy eyelet blouse and the white pants is a beautiful outfit.
😀. Great options!!!!
🙂boot flare
Did the eyelet blouse run small (since you wore a large)? It is cotton too.
I don’t think it runs small. I waver between a medium and a large.
🙂 I prefer the straight leg or boot cut. The flares do look nice. I may check these out.
Found it
🙂 Great advice on the flared jeans. You also showed some really cute tops today.
😊 Sunshine looks good on you! ☀️
🙂 Jeans and Jacket!! I’m wearing an outfit you modeled last week tonight for my grandson’s school event… flare jeans and a navy sweater vest from Walmart!
🙂 I like the sophia jeans as they come in shorter length.
🙂 I like the flowy top, wedges and slight flare.
😊love the flared jeans from Amazon! I bought them last time you posted about them. Great fit and affordable price. Jeans are so expensive.
🙂 I like the look of flare jeans, but I am 5’2″ and have an issue with length.
🙂 loving the flare jeans
😊Lots of great ideas
🙂 I love wearing flare jeans. Thanks for the advice about shoes.
🙂 Good looking jeans!
😊Found it. Love the bootcut jeans for me.
😊I have sort of avoided flare jeans since it was difficult to find comfortable shoes that looked right but you now have me rethinking the idea.
😀. I’m usually a bootcut girl, but these flares look great! May have to try a pair.
Hi, Tania. I just bought a pair of dark wash flare jeans at Ann Tayler, and I am amazed at how great they feel and look. I wear these jeans with a fitted top. BTW I am more like over 80, not over 50! Let’s hear it for looking good at any age.
Bea, 80 is over 50, so that counts. Lol!
😀I love the straight leg jeans but may have to try a little flare!
: )
I’m definitely a fan of flare jeans
😁
Love that beautiful ruana. Would be great for Mother’s Day Brunch.
Found it 🙂 Thinking of several of these flares, vs some type of wide leg. Can’t decide! By the time I do, both styles will be out of style, lol!
Found it!😀
You look great in all of them! Me being only 5’2″ make me feel shorter.😣
😀 such a great selection. Thanks
😌 found it finally. Great advice. Flares are great when with right shoes and tops. I saw a momma duck with her babies on my walk. So cute! Such a sign of Spring. She was very protective 🥰.
😀 great information! I am 5’1 so I do have to be aware of proportions. I like a little flare then a bit more structured top. Thanks!
found it
😊 I am loving the flare jeans! This is my kind of trend!
🙂 LOVE LOVE LOVE tat first outfit! Can you come shopping with me please! 🙂
😊 flare jeans are great.
😀 I like the white button up shirt and flares. A simple and classy look.
😊
Love the flares, but difficult to find petite . They always seem to have limited sizes
😊 I am definitely a flare leg girl. They are so slimming and elongate my legs!
😊 I like slight flares and bootcuts best.
😊 I bought flare jeans recently and love them
🙂
the slightly flare is perfect for me, too.
😊will definetly try the walmart and old navy jeans
😊 Thank you for explaining the difference in flare & bootcut.
🙂 Like the slightly flare jeans best
🙂 Found it! I am updating my jeans, love wide leg, but I do need some flare jeans for a more slender outline. Thanks for the outfit ideas. Have a blessed week!
😊 I prefer a slight flare jean. Great outfits.
🙂 Purchased the Eyelet Long Sleeve Button V Neck Shirt in a different color in Large and had to return and repurchase for an XL. Love it!
Found it! Thanks for tips on flare jeans and what shoes pair well with them.
🙂 Found it
Found it!
I still prefer a bootcut over a flare, but I appreciate you showing the options.
Also, I also am looking at the Bare Minimum lipstick… it’s been difficult for me to find a good neutral.
🙂 I love flare jeans and how they elongate legs.
I appreciate your tip about how a pointy toe flat is best with a flare jean. I know you have said it before, and that was an ah-ha moment for me. 🙂 I love your look #2.
☺️ Love how long and lean you look in flare jeans with heels!
found it!
I only wear straight legs, flared a little much for my short legs.
:). Found it! These jeans all llok so comfy! I’m looking for some light, summer weight jeans.
😊 I’m definitely a flare and bootcut jean gal. Thanks for the stying tips.
🙂 This style of jeans is the most flattering. As I have only one pair, I should rectify that today with a pair from this great post! Have a blessed day 🙌
Found it. Unfortunately I can no longer wear heels due to foot surgery last summer. I guess I could try a low platform. Hmmm.
😊 love the eyelet shirt with the white jeans!
😀! I use to wear flares all the time until the wide leg style jean became popular. I now love wide leg jeans lol
😊I don’t own any flare jeans at the moment. I like the look of the classic button down shirt and the eyelet top paired with the jeans. My climate is hot so my jean wearing days are quickly coming to an end until the fall!
🙂 my go to jean is slightly flared.
😊
I have not tried flare jeans since high school.
Need to give them a try again. I like the ones you styled that have a “slight” flare instead of the big flare. We used to call them “bell bottom” jeans.
I prefer the slight flare also.