As Seen On WGN-TV: How To Love Wearing Jeans Over 50

Watch the segment on the WGN-TV Website

If you caught my recent segment on WGN-TV on “How to Love Wearing Jeans Over 50” you know I love helping women 50+ feel confident and modern in their jeans. Denim doesn’t have an expiration date — the key is choosing the right cut, rise, and wash for your body type and lifestyle.

In this post, I’m sharing:

The exact jeans I showed on air (“As Seen on the Segment”)
How to match jean styles to your body type
A glossary of denim styles (so you never wonder what “cropped flare” means again!)
How different denim washes flatter different shapes
My stylist tips for fit, fabrics, and finishes
Easy do’s & don’ts for jeans after 50
Wear To Shop

**This post contains affiliate links and I will be compensated if you make a purchase after clicking on my links. Amazon prices are as of 9/14/25.

As Seen on the Segment

Erica: Skinny Jeans

Erica is modeling the “return of the skinny jean”, styled in a more modern way with a loafer, as compared to the typical ankle bootie from years past. Another updated look for the skinny jean for 2025 is tucking them into knee boots. Erica’s jeans are from Express. You can shop her entire look below.

Shop Erica’s Look:

If you’re not ready to go back to the skinny jean, straight leg jeans are a great option. Here is the difference between the two styles:

Skinny: Hugs the body from waist to ankle, very fitted throughout.
Straight: Skims the body, falling in a clean line from knee to hem — less tight, more classic.

Lesly: Denim-On-Denim

Lesly is modeling the “denim-on-denim” (or “Canadian Tuxedo”) trend with a matching blazer and bootcut jeans. We’re adding in a touch of one fall’s biggest colors, burgundy. Lesly’s look can easily be a “day-to-night” look. She can wear this to the office and then out to dinner. Lesly’s jeans and blazer are from Ann Taylor.

Shop Lesly’s look:

Do’s & Don’ts of Denim-on-Denim

Do:

Choose similar washes for a polished, intentional look
Add a belt or statement accessory to break up the denim
Pair with tailored shoes (loafers, block heels, ankle boots)
Keep proportions balanced (slim top with wide jeans, or fitted jeans with relaxed jacket)
Opt for dark washes if you’re wearing denim to work

Don’t:

Mix too many distressed pieces (rips + frays can look sloppy)
Over-accessorize — let the denim be the star
Pair with overly casual sneakers if you want a professional vibe
Wear mismatched washes unless you’re going for a very casual, fashion-forward look

LeeAnn: Relaxed 90’s Jeans

LeeAnn is modeling the classic 90’s relaxed jean, but with a modern twist: the split hem. What we like about these jeans is that they are a more casual jean but they are tailored in the thighs and waist to prevent a frumpy look. We’re keeping the rest simple to let the “jeans do the talking” but added the fun and trendy fringe bag. LeeAnn’s jeans are from Abercrombie & Fitch.

Shop LeeAnn’s look:

What are “relaxed jeans”?

Fit: High-rise, looser through the hip and thigh, with a straight or slightly tapered leg. T
Look: Casual, slightly slouchy, effortless.
Best Compare To: They’re like a more relaxed version of the straight-leg jean — less fitted, more room in the thigh, and a touch more attitude.

Natalie: Flare Jeans

Natalie is modeling the classic flare jean with an overall classic look – blazer, pumps and gold chain handbag. If you want to stay classic with a modern feel, the flare jean is perfect. Natalie’s jeans are from Chico’s.

Shop Natalie’s Look:

What’s the difference between Natalie’s flare jeans and Lesly’s boot cut jeans? Here’s a comparison of the two – as compared to wide-leg jeans.

Bootcut: Slim through the thigh, slight flare at the hem to fit over boots.
Flare: Fitted through thigh, then a more dramatic bell-shaped opening from the knee down.
Wide-Leg: Looser from hip all the way down, creating a column of fabric.

Dianne: Barrel Jeans

The barrel jeans can be a little bit intimidating to wear. My body type is an inverted triangle, so the style works well for me. The barrel jean, in general, is high-waisted with a curved, rounded leg that tapers at the ankle — almost like an exaggerated balloon shape.

I’ve styled my barrel jeans with a cropped sweater — the shorter length balances out the volume of the jeans and highlights the waistline. It keeps the look modern and proportioned, so the jeans feel fashion-forward instead of overwhelming. This combo works especially well if you want to dip your toe into the trend without committing to a full oversized silhouette.

Shop my look:

Jeans Over 50: The Best For Your Body Type

Every woman has unique proportions — the right jean can balance, flatter, and elongate. This becomes even more important as we start shopping jeans over 50.

Want to figure out your body type? Take this quiz.

Round/Apple → Mid-rise straight or slim-leg with stretch (smooths midsection)
Triangle/Pear → Dark-wash bootcut, flare, or relaxed fit (balances hips and thighs)
Inverted Triangle → Barrel or relaxed jeans (volume on bottom balances shoulders)
Hourglass → High-rise straight leg or bootcut (keeps waist defined)
Rectangle → Boyfriend, barrel, or wide-leg with belt (adds shape/curves)

Denim Glossary: Know Your Cuts

Straight-Leg: Classic, works on almost everyone
Bootcut: Slight flare, balances hips
Flare: Wider from knee down, elongates legs
Wide-Leg: Fashion-forward, roomy through thigh
Skinny: Slim fit, best with tunics or layered looks
Boyfriend: Relaxed, casual vibe
Cropped: Hits at ankle or above, great for showing shoes
Barrel Jeans: Curved leg that tapers at the ankle — modern and adds shape
Relaxed Jeans: Looser fit through hip and thigh, easy comfort without looking sloppy
High-Rise vs Mid-Rise vs Low-Rise: Where it sits on the waist

How Wash Impacts Style & Body Type

The cut of your jeans matters — but so does the wash. The right color can flatter, elongate, or add balance to your frame.

Dark Wash: Slimming, elongating, and dressy. Perfect for pear and apple shapes. Works beautifully in straight, bootcut, flare, or relaxed styles.
Medium Wash: Casual and versatile. Great for rectangles and hourglasses; pairs well with boyfriend, relaxed, or barrel jeans.
Light Wash: Trendy and adds volume visually. Best for rectangles and inverted triangles (balances wider shoulders). Looks fresh in barrel, wide-leg, and boyfriend styles.
Black or Coated Denim: Sleek and elongating. A smart choice for apples and pears. Chic in skinny, straight, or flare cuts.
White or Off-White: Crisp and modern, especially in fall/winter. Flatters hourglass and rectangle shapes. Best in straight, wide-leg, or cropped flare styles.

Fit, Fabric & Features

Rise: High-rise elongates, mid-rise offers comfort.
Stretch: A touch of elastane = comfort, but too much = saggy.
Wash: Darker washes = dressier, slimming.
Details: Minimal whiskering/distressing looks more polished.
Inseam: Don’t be afraid of tailoring — hemmed jeans always look intentional.
Barrel/Relaxed: Pay attention to length; both styles look modern when hem hits at the ankle and shoes are visible.

Do’s & Don’ts for Jeans Over 50

Do:

Invest in quality denim with good stretch and recovery (no sagging knees).
Choose mid-to-high rises for a smooth, flattering waistline.
Tailor the hem — jeans that graze the ankle or shoe look polished.
Try new silhouettes (straight, wide-leg, barrel) — it keeps your look current.
Use denim as a neutral: dress it up with blazers, silk tops, or structured knits.

Don’t:

Don’t settle for jeans that gap at the waist — brands now design for curves.
Don’t overdo distressing, whiskering, or embellishment — a touch is modern, too much looks dated.
Don’t wear jeans that puddle on the floor — it shortens your frame instantly.
Don’t cling to only one style (like skinnies) — variety helps you look fresh.
Don’t be afraid of tailoring — hemming or taking in the waist is worth it for the perfect fit.

Where to Shop for Jeans Over 50

Not all denim is created equal — and not all stores serve the same audience. Here’s a quick guide to help you know where to start your search and to let you know what each brand does best.

$ = Budget (< $70)
$$ = Mid ($70–$150)
$$$ = Premium ($150–$250)
$$$$ = Designer ($250+)

Abercrombie + Fitch $$

Best For: Curve-friendly, trendy rebrand (wide-leg, 90s straight, relaxed)
Fit & Size Notes: Inclusive sizing with petite, tall, and curve lines.
Price Range: $70–$120

Amazon Essentials $

Best For: Budget basics (straight, skinny)
Fit & Size Notes: Broad size range, limited inseam variety.
Price Range: $25–$45

Ann Taylor $$

Best For: Polished, career denim (dark wash straight/slim)
Fit & Size Notes: Petite and tall available; limited plus.
Price Range: $80–$120

Banana Republic $$-$$$

Best For: Elevated, work-friendly denim (trouser jeans, slim-straight, wide-leg)
Fit & Size Notes: Petite and tall available; limited plus options.
Price Range: $100–$200

Chico’s $$

Best For: Comfort and stretch, ankle-length fits women 50+
Fit & Size Notes: Petites and some tall; sizes convert to approx. 2–20.
Price Range: $80–$120

Democracy $$

Best For: Everyday flattering jeans (“Ab-solution” waistband)
Fit & Size Notes: Regular, petite, and plus available.
Price Range: $60–$90

Everlane $$

Best For: Minimalist, sustainable denim (rigid and stretch)
Fit & Size Notes: Sizes up to 33 waist; less inclusive for petites/plus.
Price Range: $80–$140

Gap $

Best For: Reliable everyday styles (straight, wide-leg, relaxed)
Fit & Size Notes: Petite, tall, and plus widely available.
Price Range: $60–$90 (often on sale $40–$60)

Gloria Vanderbilt $

Best For: Classic comfort jeans (Amanda pull-on)
Fit & Size Notes: Very inclusive — misses, petite, and plus.
Price Range: $30–$45

Lee $

Best For: Affordable classics (straight, bootcut)
Fit & Size Notes: Petites, plus, and varying lengths widely available.
Price Range: $35–$60

Levi’s $-$$

Best For: Timeless denim (501s, straight, bootcut, barrel)
Fit & Size Notes: Wide range of inseams; petite and plus on Levi’s.com/Amazon.
Price Range: $60–$120

Loft $