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In 17 years as a personal shopper in Chicago, I watched women over 40 walk into my fitting room swearing they were done with jeans and walk out with two pairs. The trick was never the label. It was the rise and the hem. These 8 jeans women over 40 are wearing this fall show which cuts came back and which ones are new.
Gray is taking over from blue this fall. Harper’s Bazaar UK noted that “in recent weeks, everyone from Victoria Beckham to Katie Holmes has stepped out in a pair of smoky-grey jeans.” Beckham is 52, and Holmes is 47.
The same article explains why they are easy to wear: grey jeans are “the perfect foundation for richer autumnal hues, but will work just as well paired with classic neutrals like black and navy.” Try them with a rust or camel sweater, or keep the whole outfit in gray and navy.

At a SAG-AFTRA Foundation panel for her film Wicker, Olivia Colman, 52, wore a herringbone blazer, a white T-shirt and wide-leg jeans with a pressed front seam and a long hem. Harper’s Bazaar UK wrote that “Colman looked typically stylish in a herringbone blazer, white T-shirt and polished wide-leg jeans.”
The magazine’s explanation: “the reason wide-leg jeans work so well with blazers is that they’re exactly that: considered.” Let the hem fall long, over a low boot or a loafer.

On October 20 in Beverly Hills, Sofía Vergara, 54, was photographed “slipping into a pair of light-wash barrel jeans” with a gray vintage band T-shirt, black sunglasses and black sandals, Harper’s Bazaar reported.
Denim specialist and stylist Sahra Brandt told People that barrel jeans “are so comfortable that once you try them, you become a convert.” Her tip: “Wear them with a fitted top and ballet flats to up the ‘cool factor.’” A slim knit on top keeps the curved leg the focus.
From the author:
My fitting-room test for any new cut had three moves: sit down, reach up, then walk to the end of the hall and back. If the jeans passed all three, we talked about the price. If they failed one, no amount of “they’ll stretch” saved them. Wide legs and barrel jeans pass more often than people expect.
In late September in Milan, during fashion week, People spotted Jennifer Lopez, 57, “wearing retro flare jeans on an outing,” with a crisp button-up shirt, pointed-toe heels and a sleek black tote.
The magazine’s advice for the rest of us: “Dress them up with a button-up and heels à la Lopez this fall, or keep them cozy with a sweater and boots on chilly days.” Flares look best when the hem nearly touches the floor, so try them on with the shoes you plan to wear.
Julia Roberts’ stylist Elizabeth Stewart shared the look from a dinner in Paris in October: a chartreuse cardigan, slim jeans with a slightly Western cut and heeled boots. Harper’s Bazaar UK wrote that “Roberts proved that nothing beats the classic jeans-and-boots formula at this time of year.”
A bright knit is the easiest way to make jeans feel dressed up for dinner. Keep the boots and the jeans in close shades, so the leg reads as one line.
“Choose chartreuse💚”

From the author:
Most of my clients didn’t need new jeans. They needed a hem. My tailor of 20 years, Sol, takes one look and says “half an inch,” and he’s right about nine times out of ten. A good hem is the cheapest way to make jeans from any decade look like this season.
At a brand event in New York in early October, Keri Russell, 50, wore a cropped plaid field jacket, a white top and straight jeans with folded cuffs. People wrote that “the folded cuffs on Russell’s jeans are a small detail that makes a basic denim outfit look more interesting.”
For the shoes, Harper’s Bazaar UK’s advice for cuffed jeans is simple: “if you prefer flats, then a smart loafer works well.” A wide cuff also shows off a pretty sock, which is half the fun in October.
“Can you wear white jeans in the fall? According to Gwyneth Paltrow, absolutely,” People wrote in September. Paltrow, 54, “started with white wide-leg jeans, added a neutral lightweight sweater (one black, one gray), and finished with red ballet flats.”
Elle’s Lauren Gruber agrees: “Crisp white denim happens to be the ideal base for this season’s staples—think khaki trench coats, colorful knitwear, and leather bombers.”
In mid-October in New York, Oprah, 72, wore medium-wash wide-leg jeans with a cropped denim jacket in nearly the same wash, a red handbag and brown pointed-toe heels. InStyle called the outfit a “Canadian Tuxedo.”
For fall, Harper’s Bazaar’s Kristina Rutkowski noted that “designers proved doubling up on indigo denim is the move.” Keep the two washes close, as Oprah did, and add one bright accessory.
The last look on this list is double denim, and Oprah wears it like a decision, not an accident. That was always the goal in my fitting room: jeans that look chosen. Half an inch at the hem usually did the rest.
Which jeans from your closet would you never give up, whatever the trends say? Tell us in the comments.











