How to Style this Season's Favorite Jeans—Flare Jeans—for Women Over 50 for Every Occasion: 7 Looks

Anna Traver

August 19, 2024 at 7:08 PM·8 min read

When it comes to fashion, the old adage holds true: everything old is new again. And while some styles are better left in the past, we're seeing the return of one that we can get on board with: flare jeans from the 70s. We're not talking full-on bell bottoms, but a more modernized version of the flowy-bottom pant style, also considered boot cut jeans. The leg-elongating design has been seen on many celebrities like Heidi Klum and Padma Lakshmi, and we're declaring it the "it" jean of fall. To get all the expert tips on wearing the trendy pants, we asked a celebrity stylist how to style flare jeans for any occasion you may reach for them this season. Here, seven looks you're sure to love.

Why are flare jeans flattering on women over 50?

Padma Lakshmi wearing flare jeans — Getty

As women, the struggle to find the perfect jean that checks off all our boxes is universal. We want a pair that highlights our features, makes us feel confident and has some stretch; after all, you want to feel comfortable in the more casual piece of clothing. To the rescue: flare jeans, like the ones 53-year-old Padma Lakshmi is donning above.

The key to getting the most out of the jean is how you style them. "Flare jeans can elongate a leg, especially when you get the proportion correct with the top," explains celebrity stylist Eric Himel, who has worked with Giuliana Rancic and Tia Mowry. "Think of the 1/3 and 2/3’s rule: your top should take up 1/3 of your silhouette and your jeans 2/3s." For example, when putting an outfit together with flare jeans, opting for a shorter top helps give the figure more balance. "Too long of a shirt can add unnecessary bulk," he explains.

How to style flare jeans 7 different ways

See stylists' favorite ways to style flare jeans on women over 50 for any occasion.

We love how Heidi Klum, age 50, took these seemingly casual flares and dressed them up with a lace top and fur jacket.

1. How to style flare jeans for a casual lunch

how to style flare jeans for lunch — N/A

A pair of light wash flared-denim is a great staple to add to your closet, especially for more casual day plans. They can be easily be dressed up or down: throw on a comfy, cozy sweater and a pair of flats for lunch with the girls and swap out the flats for heels for dinner plans. These flare jeans from Express have enough stretch to keep you comfortable, but won't lose their shape as the day goes on. The peach sweater features flare sleeves to match the shape of the pants which adds even more body-beautifying balance. You can tuck in the front for a more cohesive look or let it hang loose for a more effortless style.

Shop the look:

Light wash flare jeans: Buy from Express, $98

Peach flare sleeve sweater: Buy from NA-KD, $49.99

Black bow flats: Buy from Target, $47.99

Black purse: Buy from Amazon, $25.90

Gold earrings: Buy from Amazon, $11.99

Pearl necklace: Buy from Flaire & Co., $23

2. How to style flare jeans for a night out

What we love even more about flare jeans is they can easily be dressed up for a dinner date or office party. Simply reach for a dark wash shade (dark wash typically looks dressier), like these LOFT dark wash flare jeans, and pair it with a sexy, yet elegant off-the-shoulder top. The olive green of this Aritzia top is spot on for fall and feels thick and high-quality. The bare shoulder tastefully shows off some skin while still remaining chic. And, the length of the shirt cuts off right above the jeans, following Himel's 2:1 pants to top ratio.

And finish it off with a pair of comfy statement heels (cheetah print is back!), a simple clutch, a chic necklace and earrings. You'll be sure to wow any crowd!

Shop the look:

Dark wash flare jeans: Buy from LOFT, $89.95

Olive green off-the-shoulder top: Buy from Aritzia, $48

Cheetah print heels: Buy from DSW, $39.99

Black shoulder bag: Buy from Amazon, $26.99

Necklace: Buy from Anthropologie, $58

Earrings: Buy from Amazon, $12.99

Amanda Holden wearing flare jeans — Getty

The pop of red in 52-year-old Amanda Holden's outfit with her pointed toe shoes and long trench help liven up the style in a bold and chic manner.

3. How to style flare jeans for happy hour

A cocktail hour with friends, family or coworkers is not only a chance to catch up and unwind with a glass of wine (or two), but it's also the perfect opportunity to get dressed up in a fun and cute way. Sure, we know that wearing head-to-toe black is a classic, but adding a pop of color, like this season's hottest color deep red, is a bold way to add pizazz to the all-black look. Himel suggests pairing black flare jeans with a pointed toe shoe, such as these pointed toe booties. "A pointed toe is narrow — so it gives the illusion of your legs looking longer." Plus, he adds, "a flared jean looks great with a heel — your choice if it's a low, mid or high heel. And I am just loving a pointed mid-heeled boot right now with a flare jean." The two together create a double leg-flattering effect.

Shop the look:

Black flare jeans: Buy from Old Navy, $36.99

Red leather jacket: Buy from Amazon, $45.99

Black top: Buy from Zara, $25.90

Red purse: Buy from Amazon, $28.99

Black booties: Buy from Famous Footwear, $59.99

4. How to style flare jeans for work

Dark wash flare jeans keep a work outfit from looking too casual and pairing with a delicate blush blouse with a subtle detail, such as these sheer sleeves, helps add a little work-day elegance. These flare jeans from Lane Bryant are an amazing plus-size denim option. They have a high-rise waistband that will feel comfortable all day. A pair of loafers are the perfect shoe for the office, and this brown tote bag will hold all of your essentials for the work day. Finish it off with a gold knotted necklace.

Shop the look:

Plus-size flare jean: Buy from Lane Bryant, $79.95

Blush blouse: Buy from Anthropologie, $88

Loafers: Buy from DSW, 59.99

Brown tote bag: Buy from Amazon, $15.99

Gold knot necklace: Buy from Amazon, $16.99

Jennifer Lopez wearing flare jeans — Pierre Suu / Contributor / Getty

Jennifer Lopez, 55, keeps it simple with a pair of flare jeans and a classic white long sleeve tee.

5. How to style flare jeans for errands

how to style flare jeans to run errands — N/A

We know jeans may not be the first thing you want to throw on when running errands, but some days putting a little effort into your ensemble, even while on a Target run, can just boost your mood. These ankle length flare jeans from Zara are the perfect way to do it. They have stretch and mobility, easy to slip in and out of and cost less than $50!

Add a plaid, cropped shacket over a brown tee — following Himel's "1/3 top, 2/3s bottoms" rule — to stay warm and cozy. A pair of white, slip-on sneakers are a great staple to have in your shoe collection and are an ultra comfortable option if you're going to be on your feet all day. Keep it simple with accessories by adding a gold watch.

Shop the look:

Ankle flare jeans: Buy from Zara, $45.90

Brown tee: Buy from Old Navy, $12.99

Plaid shacket: Buy from Venus, $69.90

White slip-on sneakers: Buy from Amazon, $59.97

Gold watch: Buy from Amazon, $24.50

Charisma Carpenter wearing flare jeans — Getty

Charisma Carpenter, age 53, sports a pair of medium wash flare jeans paired with a tucked in mockneck sweater.

6. How to style flare jeans for a family outing

how to style flare jeans for family outing — N/A

Have a fun, family activity planned for the weekend? Head to the apple orchard or grab some hot chocolate in style. A cream flare jean changes up the typical blue denim, and looks luxe against a rich, chocolate brown, short sleeve sweater, great for those days that aren't too cold but not too warm. Pair with your favorite brown accessories, such as a chocolate brown bootie and a houndstooth crossbody purse. Top it off with a gold layered necklace and sassy gold earrings.

Shop the look:

Cream flare jeans: Buy from Express, $69.99

Brown short sleeve sweater: Buy from T.J. Maxx, $14.99

Gold earrings: Buy from Amazon, $12.99

Gold layered necklace: Buy from J. Crew Factory, $19.50

Brown houndstooth purse: Buy from Amazon, $24.99

Brown booties: Buy from DSW, $29.98

7. How to style flare jeans for a party

how to style flare jeans for party — N/A

Dressing up a pair of flare jeans may be easier than you think when you add a pair of heels and a rhinestone clutch. For a non-formal party, this is a stylish yet comfortable choice. And a sequined vest adds a sophisticated touch of sparkle, while pearl accents on a necklace and earrings give the look some feminine flair without competing with the sweater.