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How to Find Just-Right Jeans for Stylish Older Women in 2024

These five questions can lead you to true-blue wardrobe staples.

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photo collage of comfortable blue jeans for stylish older women
Ethel Staff (Getty Images, 5)
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Goldilocks had it easy. She only had three choices before finding her just-right bed. When it comes to jeans, finding your just-right pair is complicated by dozens of variables that can lead you down a long and twisting path.

To make your search easier and faster, spend some time answering these five questions. They are the result of my own personal jean journey that involved ordering more than two dozen pairs from a range of brands, from new to pre-owned. At the time, all were under $100. Several are frequently on sale or can be reduced further by signing up for email promotions or loyalty programs.

Where do I plan to wear them? The jeans you wear around the house may look different from the jeans you wear to run errands or to meet friends. Will one pair cover all those bases? That depends on you and your fondness for denim. A teen in the ‘70s, I grew up wearing jeans and am a lifelong fan who likes having a couple of reliable options in my closet.

As I write this, I’m wearing a $32 pair of Universal Thread’s High Rise ‘90s Slims from Target that was purchased in a pinch. While visiting my 88-year-old mom, who also has her go-to jeans, I needed an extra pair for yard work.

A dash to the nearest store located jeans that were up to the task but not necessarily perfect. They were a size too big and had two things I’d previously avoided — a button fly and a raw hem. On the flip side, their sturdy cotton provided protection from rash-inducing vines and the cut was roomy enough for active use — and later to slip a base layer of long underwear beneath.

They are a comfortable solution for around the house but inspired me to do a more thoughtful jean refresh. My last one was more than five years ago. It was time.

How trendy do I want to be? Right now, you can find denim in everything from ‘70s flares to ‘80s cargos to ‘90s straights. Wide, loose legs are the current fashion-set favorite and are great for those who’ve struggled with too-tight styles through the years. However, if you’re just now breaking up with your skinny jeans, you can go with a less extreme straight cut.

After canvassing a trio of dependable resources — Wirecutter, The Strategist and Who What Wear — I took note of frequently recommended styles and brands, then compiled my list of jeans to try. I checked buyers’ reviews and was encouraged to see assessments from those like me in their 60s. Then, I held my breath and started tapping the order buttons.

What’s my comfort threshold? If your biggest regret from the ‘70s is not having Lycra in your jeans, this is your chance to embrace the comfort of 1 percent stretch with some old-school styling. Now called “rigid,” all-cotton versions are available but often feel restrictive.

For those living in a warm climate, the fabric of your jeans may be a factor too. Typically, higher cotton content indicates a heavier and sturdier fabric. Higher percentages of manmade fibers signal a lighter-weight fabric with more give but a shorter lifespan.

While listing fabric content has universal standards, the vocabulary in styling descriptions can vary widely. What one brand considers mid-rise may be another’s high-rise — a trendy cut that holds tummies in but often requires upsizing to avoid any overflow at the waistband. Similarly, terms like snug, slim and straight are open to wide interpretations.

The bottom line? Be prepared to place follow-up orders after you see how things are fitting. My first order from The Gap was all too tight. The next arrivals from Madewell were too big — even though they were the same waist size. I pivoted on my next attempts, ordering two waist sizes — the current and one up — and making sure they qualified for free delivery.

Which details are deal breakers? Finding a just-right fit is hard enough, but then there are all the other factors to consider: color and stitching, flies, fabrics and finished vs. raw hems.

When deciding on color, keep in mind that darker washes tend to be dressier and light washes trendier. Which shade you choose also can affect the fabric they’re made of. It’s no longer a given that the same style will be made of the same fabric just in a different blue. Simply clicking a different color balloon while online shopping can determine not only the look but also the feel of your jeans.

Another detail that’s often missed — the type of fly. Retro button flies are increasingly common so be on the lookout if arthritis makes these fasteners a challenge for you.

The moral of the story? Always, always read garment descriptions carefully. And enlarge photos to scan for other telltale signs that might be your deal breakers.

What’s my budget? Saving the best for last, I am happy to report you can find plenty of flattering, well-made jeans with reasonable price tags. With a little sleuthing, you can even nab pre-owned pairs from celebrated brands on ThredUp for under $15. You can also buy pre-owned pairs on Etsy. The current preference for jeans with a lived-in look makes this an easy win — for your wardrobe and your wallet.

My jean journey came to an end after trying on 26 pairs multiple times for a thorough evaluation. Luckily, most online stores have easy return options, so I didn't have to keep them all.

I discovered what I thought I wanted wasn’t really the answer, just misplaced nostalgia. Instead, a highly recommended, button-fly style from the iconic Levi’s brand won me over. Despite its somewhat unfortunate name, the Wedgie Straight Fit Jean from Levi’s Premium collection has a revered fit, the added comfort of 1 percent stretch and (thanks to a sale code and loyalty member discount) a price tag of $58.00 at the time.

I also ended up with two pairs of Gap jeans from ThredUp for $13.20 and $12.10. The latter was an unexpected “final sale” in lighter-weight denim and the other a highly praised ‘90s straight style with a mid-rise cut. Unlike the Wedgie, they both have zip flies.

Now it’s your turn! If you’re looking to refresh your denim, answering these five questions can help you find the just-right jeans that will become your next true-blue wardrobe staple.

Do you still wear jeans? Where do you buy them? Let us know in the comments below.

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