I’m 52 years old. During my life, jeans fashion has gone from bell bottoms to acid-wash to ripped to boot-cut to low-rise to skinny to high-rise to mom jeans to ripped again to wide-leg. … Please make it stop. I don’t have another jeans transition left in me. Is there a timeless jeans style for those of us who simply cannot keep up? — Annie, Seattle
I feel your pain — or at least your sense of not being able to keep up. On the Levi’s website there are six different styles of jeans for women and for men (barrel, baggy, straight, etc.). That’s a lot of choice, but all of those general styles are further subdivided into multiple numbered choices (the 500 series, the 700 series, the 300 series and so on) all with a variety of rises, colors and treatments, meaning there are more than two dozen possible denim options.
And that’s just one brand. There are also stores devoted solely to laying out the full landscape of jeans, as if it were a potentially foreign land, full of mysterious grommets and inseams. Not to mention jeanfluencers to guide you.
I point this out not to further confuse the issue but to underscore how multitudinous the current choice of denim is. It’s easy to look at that offering and think: Help! But rather than feel overwhelmed by it, try to see it as it is: a reflection of the fact that there is simply no one dominant kind of jeans anymore. And that’s actually a good thing.
Gone are the days when everyone had to wear low-rise, or skinny or boot-cut jeans (even if barrel jeans seem to getting all the attention these days). Instead we are now living in a world of jeans diversity, where every style is available and acceptable at the same time.
That’s why, for example, Catherine, Princess of Wales, continues to be loyal to the same skinny jeans she has been wearing since she burst onto the public stage some two decades ago. It’s why Jennifer Aniston is still in her straight-leg styles. It’s why, when Beyoncé released her album “Cowboy Carter,” she also masterminded her own bedazzled Levi’s (or Levii’s) denim collaboration. It’s why so many brands now seems to offer an assortment of denim. To a certain extent, every jeans style is now a timeless jeans style.
If, however, all of these options are simply overwhelming, Benjamin Talley Smith, the go-to guy when a designer wants to build a denim line, has the simplest answer: a “classic straight leg.” Smith said when he starts working for a new brand, that’s the first thing he designs. (See, for example, the Khaite Abigail, the Reformation Cynthia and the Free Assembly Original 90s Straight, all of which he helped create.) It’s a style that “will look just as great now as it would five years from now,” he said.
Especially, he continued, if you opt for a light blue wash or, if you want jeans that can be more dressed up, a darker one. Choose a longer inseam rather than a cropped one for maximum versatility, since longer can be worn with flat shoes as well as rolled up to go with heels. “And stick with rigid fabric, as it will be more durable and last longer,” he said.
The one thing to avoid: trendy design details, “like embroidery or pocket flaps,” Talley Smith said, since those are the tells that can trap a style in time.
Similar advice came from Jane Herman, a daughter of the Los Angeles retailer Ron Herman and a denim obsessive (she writes the Jane on Jeans Substack), who told the “Who What Wear” podcast that any jeans wardrobe starts with “high-rise straight-leg jeans of some kind.” She called it “the archetype of a pair of jeans” and said, “When you close your eyes, you think of a five-pocket jean in its most classic form.”
What all of this means is that you don’t actually have to choose. Years ago ShopSmart did a study that is still widely cited, which found that the average American woman owned seven pairs of jeans. Assuming you have accumulated your own denim assortment over time, you can simply see how you are feeling on any given day. Consider what style fits your body best at the moment, or makes you feel the most confident, or is the most multipurpose for your life, or is just the most comfortable.
That’s the one to wear.
Your Style Questions, Answered
Every week, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or X. Questions are edited and condensed.
