Fashion & Beauty

An Opinionated Guide to Buying Jeans

It’s all about your jeans. From left to right: A wide leg from Universal Standard, a barrel shape from Ayr and a “girlfriend” style from the Gap.

By MyLittleBird Staff

BACK WHEN dinosaurs roamed the Earth, there were three jean manufacturers I can think of —Levi’s, Wrangler, and Lee–and more or less one look for everyone. Fast-forward to 2023, and there are so many brands and styles, they could make your head spin around faster than Linda Blair’s in The Exorcist.

Although skinny jeans predominated over the past 15 years or so, thankfully for many, those tight, body-hugging silhouettes have had their day in the sun, and the fashion cycle now favors styles with wide, flared and cropped legs, as well straight and bootcut styles. Also, the zeitgeist is headed in the direction of looser and more comfortable, so we’re also seeing several baggy/oversize options. Remember the low-rise jeans of the early 2000s? They’re back, albeit with more coverage than in the past. And, lest we forget to mention it, roomy cargo jeans with large pockets are getting their fair share of likes.

All that said, Nancy and I thought we should weigh in with our completely biased opinions on the subject. But our third partner in crime, art director Kathy Legg (Louie to our Huey and Dewey) was having none of it. Although the demise of skinny jeans delighted her, no other styles brought her any joy.

“Maybe I just don’t like jeans. Haven’t worn them in decades. Never found them all that comfortable. Too many stiff, hard seams. And they never fit me. Accommodating my hips meant about 4 extra inches in the waist. And the last thing those of us with pot bellies need is a bulky zipper in the front.”

Okay, then, that leaves Nancy and me (Janet) to carry on. In the name of jeans, of course.

Janet: With all due respect to Levi’s of long ago and to a passion for vintage jeans, I say if there’s no stretch, no way. Elastane, also known as Lycra, is the stretchy synthetic fiber that allows for figure-sculpting cuts, and these Levi’s 501 Originals ($108) don’t have a smidgen. Boyish figures out there with no hips, not much of a tummy and slim legs—you know who you are—these may be your perfect pair.

Nancy: Good point, Janet. I’ve recently come back from half a century of not wearing jeans, of envying my slim sister as she practically lived in them. As I eased into a pair a few years ago, I felt quite comfortable in them but didn’t wonder why. As Janet points out, however, it was the jeans that had changed, not me. Chances are I’d find these vintage-style Levi’s too restrictive for my various bulges. Let’s hear it for Lycra!

Janet: I have only a teeny-weeny bone to pick with these H&M flared jeans —which sell for $39.99. I would prefer that the waist were higher, which would have more of a waist-whittling effect and balance out the wider leg. I’m kind of obsessed by the question of what shoes go with what pants, so although I like the stack-heeled sandal shown above, I’d wear these with ankle boots, a low, pointed pump or maybe black Converse sneakers.

Nancy: And I don’t think I’d wear them at all. Having no waist to “whittle,” I wear looser tops with pants of any kind. But it’s not good to flare on top and on bottom. As Wendy, a genius saleswoman in the plus-size department of Bloomingdale’s, told me years ago, with a large frame you gotta cinch in somewhere. I frequently see this style shown for those of more moderate size accompanied not by heels but sneakers. That’s maybe a bit too casual, possibly bordering on the sloppy, but a canvas slip-on could carry the look and ramp up the comfort.



Nancy: This “boyfriend” look is one I like. For one thing, it gives me the excuse to roll up pant legs that always seem to be too long. And even though Janet has explained to me (and others) that a longer pant leg stretching down to hit a shoe of the same tone gives a longer, leaner look, I often feel nailed to the floor in that configuration. I like letting my ankles and legs free to be. They’re similar to a pair my sister just bought, after wearing her last “basic” jeans just about every day of lockdown. Also, she fell while navigating the dicey sidewalks of her town and ripped another pair. She’s forgoing the shredded and ripped trend, will leave that to the kids. (Note to Pat: not a shredded pair in the story!)

Janet: First of all, thank you, Gap, for making jeans that ring in under $100 —they’re $69.95, but with a 40% store code, will set you back a lot less. Nancy, to clarify, the Gap calls these “girlfriend” jeans. They’re cut higher, have a more tapered leg and hold you in at the hips and waist. In other words, they’re similar to the boyfriend but will show off your curves.


Janet: I don’t think Nancy won’t agree, but I love the elongated silhouette on Paige’s high-rise, Montecito flare jeans.  What’s not to like about legs that look like they go on forever? Note that the dark wash here grants the gams a slimming boost. Moreover, their shape, with a slight flare from the knee to the hem, makes everyone imagine you’ve got slim hips and a narrow waist.

Nancy: Right! This is my nailed-to-the-floor look! (Note to Janet: This model’s legs do go on forever!) I could give this look another try, especially if it would make stumpy legs look long, but I’m also clumsy! The potential for tripping is at least psychologically present. If I were to hazard the look, I’d choose an inseam significantly shorter than shown here. And I see too many people walking around with the back hem worn away under their heel to make this an attractive look to my eye.


Janet: I like the relaxed vibe of Universal Standard’s high-rise, wide-leg jeans, which also comes in indigo and black if you prefer darker washes. My only caveat is to be careful this loose look doesn’t turn sloppy. The key is to keep the top half slim and trim.

Nancy: Yes, feet free and clear! And a little bit of bounce from the flare (and that deep, deep hem). But amen to what Janet says about the top half being the make-it-or-break-it element.


Nancy: It’s not that I’m in love with my ankles. It’s more what I’ve said (endlessly) above: I like a beginning and an end, and the casual vibe the crop gives off. To me crops mean spring and summer. This barrel cut doesn’t register with me as fashion: It just seems roomy. And because it doesn’t flare at the bottom, I think a looser top might work. Janet?

Janet: These barrel-leg jeans from Ayr look so darn comfortable, plus they hit at the ankle sweet spot, have some stretch and come in a summery straw color and in the palest pink, too. Yes, Nancy, because the legs are straight, you can play with the proportions on top.


Janet: These Citizens of Humanity easy cargo jeans in a light wash denim have a relaxed straight leg that tapers at the ankle (no tripping hazard). The large pocket-embellishments sitting on one’s thighs have no function, they look to me more like a subtle detail. As for the wash, I approve.

Nancy: No, just no. Who among us wants extra fabric pooched out over thunder thighs? I actually bought a pair in olive green when I was about 20. They were just something a little different, I thought. Then a rather cheeky nurse at the doctor’s office asked if I had joined the army. Never wore them again. I do like the length of these, though.




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9 thoughts on “An Opinionated Guide to Buying Jeans

  1. Nancy G says:

    Love your back and forth on these topics!! Skinny jeans have no place in the closet of any person over the age of 22, IMO. However, “slim” is another category, and can be long or rolled above the ankle to great effect. I actually have had a pair of the Gap Girlfriend jeans for several years, and live in them. Not too tight, just right waist, and I do wear them down in the winter with ankle boots, and rolled in the spring and summer for my flip flops. I keep looking at cargoes, but agree that those pockets on the outer thighs may not be a good look on adult women, for the most part. I’m sure there are exceptions.

    1. Janet Kelly says:

      Thanks, Nancy, and thanks for the tip on Gap Girlfriend jeans. I think the Gap is underrated sometimes. They sell basics for excellent prices.

  2. Carol says:

    Love this, the wide flared ones intrigue me but not sure how they would look on me. I do really like cropped pants, in the winter with ankle boots and the summer with whatever you like depending on the weather. Agree none of the torn looks for me although I do have a pair intentionally torn that I wear for messy jobs at home.
    Thanks to the little birds for all these thoughts. ❤️

    1. Janet Kelly says:

      You’re most welcome, Carol. The best way to find out if a jeans style looks good on you is to go try pairs from different brands. For example, a pair of flared jeans from, say, Levi’s, is not going to fit the same as a flared pair from the Gap. Keep trying is my motto.

  3. Joanne says:

    Jeans are terrific. But … how do you find a great white button-down cotton shirt to go with the jeans. Not too long, not too short…etc.

    1. Janet Kelly says:

      I like Brooks Brothers white button-downs in classic and fitted styles–and they’re frequently on sale. I would also look at options from J.Crew and Alex Mill. Frank & Eileen’s shirts are splurge-y, but they come in different fabrics and lengths.

  4. Jim Roiddey says:

    I prefer to refer to what you call “jeans” as my “men’s denim trousers.”

  5. cynthia tilson says:

    You two slay me…playful yet pragmatic advice. Just bought a pair of final sale barrel jeans with a dark wash from Banana Republic – one size smaller than what I currently wear because according to comments they run huge! They looked great on the tall, super slim model…These appear to emphasize both waist and ankles while accommodating padding on hips and thighs…wish me long legs and breathability!

    1. Janet Kelly says:

      Fingers crossed!

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