Ladies, let’s talk about flare jeans! If you’ve been keeping an eye on closets and conversation threads (yes, we’re looking at you, Reddit!), it’s clear that this timeless denim style has sparked a new sense of curiosity. Wide-leg pants are undeniably ruling the game, but what about those flare jeans sitting quietly at thrift stores or buried in your closet? In this guide, we’ll explore how to wear flare jeans over 50 for a chic look.
If you’re wondering whether flare jeans are the right fit—both for your wardrobe and your confidence—don’t worry. With Jennifer Ebelhar’s The Style Equation approach to elevated casual attire for women over 50, we’ve rounded up a list to help you confidently add flares back into your wardrobe. This includes tips on how to wear flare jeans over 50 with style and grace.
Spoiler alert: Flare jeans can absolutely work for you! It’s all about how you style them. Let’s get to it!
Understanding how to wear flare jeans over 50 can transform your wardrobe. Let’s break down the essential styling tips!
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Flare Jeans are Timeless (When Done Right)
Flares are not just a trend—they’ve endured decades for a reason. They’re universally flattering when styled correctly. If you’re over 50, don’t dismiss them as a relic of the 70s! Done right, flare jeans can elevate your casual style by balancing your silhouette and offering a touch of chic drama.
- Opt for styles with minimal distressing for a polished look.
- Stick to darker washes if you want them to feel more modern and versatile.

Let Your Legs Shine (Literally, Elongate Them!)
One of the biggest benefits of flare jeans is their ability to make your legs look miles long. This especially applies if you pair them with the right shoes.
- Choose the correct inseam! Your flares should almost skim the ground, with just a slight peek of your ankle.
- Pair them with heeled ankle boots or platform sandals to accentuate the flare—it’s the secret to rocking this silhouette.
Elevated Fashion: 4 Wardrobe Swaps That Will Make You Look Younger
Balance is Everything—Especially For Mature Wardrobes
When wearing flare jeans, proportions are key. For elevated casual attire, always aim to balance volume.
- Go for a fitted or slightly tailored top to avoid the dreaded ‘too much fabric’ look. Think tucked-in button-down shirts, soft cashmere sweaters, or tailored jackets.
- Prefer a boho vibe? Pair your flares with a flowy blouse, but balance it out by cinching your waist with a thin belt.
Jennifer’s Tip: Not sure if it works? Stand in front of a mirror and ask yourself: “Am I wearing the jeans, or are they wearing me?” Confidence is key.

Styling Your Flares for a Modern Edge
To keep your flare jeans looking updated and age-appropriate, choose complementary accessories that ooze sophistication.
- Add a trendy blazer or moto jacket for that chic, confident vibe.
- Layer subtle jewelry—a statement necklace or some gold hoops—to tie the outfit together.
- Don’t shy away from bold patterns or scarves to add personality while looking polished.

Flare Jeans for Every Occasion
With the right styling, flare jeans can transition from casual daytime errands to evening gatherings.
- Daytime Chic: Pair flares with a striped Breton top, ballet flats, and a tote bag.
- Evening Sophistication: Elevate them with a tucked-in silky blouse, block heels, and a longline blazer.
Jennifer Reminder: Fashion is all about versatility—never underestimate the power of mixing and matching! You’ll always feel more radiant when you wear outfits that work across different aspects of your lifestyle.

Confidence Always Comes First
Let’s address the elephant in the room: Feeling “ridiculous” in flares (raise your hand if you’ve thought this too!). Here’s the truth—style is completely personal. If something fits you nicely (yay for $6 thrift treasures!) and makes you smile when you see yourself in the mirror, that’s a win.
Jennifer Ebelhar’s philosophy at The Styled Equation reminds us that fashion isn’t necessarily about following the trends—it’s about wearing what makes you look and feel amazing, no matter your age.
Shop all Flare Jeans from Cabi here!
Let’s Embrace How to Wear Flare Jeans Over 50 (With Confidence!)
So, are we liking flare jeans again? With the right mindset and styling choices, the answer is a resounding yes! They’re flattering, timeless, and incredibly versatile—all qualities that align perfectly with The Styled Equation’s mission to bring effortless, elevated casual attire to women over 50.
Ladies, don’t be afraid to rock the flare. Whether you’re wearing them on a casual coffee date or strutting your way through the grocery aisle, remember this: Clothing is a tool for confidence—so use it, own it, and love it!
What’s Your Flare Style?
Have you recently given flare jeans a try? Snagged a bargain at the thrift store? Let us know in the comments below! At The Styled Equation, we’re a community of women redefining style, one outfit at a time.
