I’m a 40-Year-Old Denim Devotee Who’s Tried Hundreds of Pairs — These Are the 6 I Wear on Repeat

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For some, it’s rare sneakers, rubber soles enshrined in plastic wrap like they’re destined for the Louvre. Others hop on planes in pursuit of the next French designer bag exclusive. 

But my sartorial fetish? I’m enchanted by the power of a perfectly flattering pair of jeans.

Now that I’m in my 40s, my denim desires have evolved from twenty years ago. 

I’m seeking chic elegance, the illusion of endless legs, and above all, comfort. I want jeans that can go from weekend casual to polished and poised. My denim quest has evolved from chasing trends — like curved legs, oddly placed rips, or the nostalgic resurgence of skinny jeans — and more about foundational classics that suit my body and lifestyle. 

Best Jeans for Women in Their 40s, at a Glance

• Best Straight Leg Jeans: Frame Le Sleek Straight
• Best Bootcut Jeans: Mother The Hustler Ankle Fray
• Best High Rise Jeans: Paige Cindy 
• Best Wide Leg Jeans: DL1961 Hepburn Wide-Leg High-Rise Jeans
• Best Fashion Flare Jeans: Ramy Brook Helena High-Rise Flare Jeans
• Best Wide-Flare Jeans: Paige Marlow Flare Jean

My journey into the “Denim Head” universe began four years ago. I was in the denim section of my favorite department store, a blue jean–filled oasis, innocently shopping for one new pair. Little did I know I was about to fall prey to a rare “good denim day”—a phenomenon that only happens once every few years like a pink moon or rare eclipse.

I was working with a Sales Associate (read: Jean Whisperer) that seemed to have an incantation for every style. I found myself surrounded by thirteen transformative pairs of jeans. With each pair, there were irresistible promises: “This knit wide-leg gives off-duty super model vibes” or “For turning heads at Saturday brunch at Pastis.” And the ones that channeled a luscious ripe piece of fruit: “You want to raise your bum and make it look like a juicy peach? These.” 

How could I resist these siren calls?

Each pair not only sparked joy, but more importantly, confidence. High-rise styles showed off my waist, flowy wide-legs made me feel like my surname could be Hadid. Cropped stretchy bootcuts that lent the illusion of a subtle BBL.

While I somehow managed to leave with just one pair (the butt ones, obviously), from there I became fascinated with the most reliable of investment staples: good jeans. I began frequenting the department store’s app, hearting each pair that the Jean Whisperer introduced me to, and shrewdly watched for promos and sales.

One pair turned into a robust denim wardrobe, but for me, investing in quality jeans is an unequivocal yes. They serve as your wardrobe’s backbone, a core tenet that you reach for time and time again, whether that be for weekend errands, romantic dinners, last-minute vacations, adventures, lunches, and even for the office when paired with a chic double-breasted blazer. 

My Body Type & Size

Standing at 5’2”, my waist size fluctuates between sizes 24 and 25, depending on the brand and amount of stretch. I’ve found certain styles of denim work well with flats and others that definitely need a comfortable heel. I’m wearing platform heels with the flares and wide-leg styles pictured below, as I find that combo the most flattering on my frame.

Below, the six best jeans I’ve tested as a woman in my 40s who’s a self-professed denim lover.