Ask the Strategist: Pants-a-Palooza

In our advice column, “Ask the Strategist,” we answer your most burning shopping questions by surveying friends, calling up experts, and drawing on our own personal experience. Today, we’re answering reader questions about petite postpartum pants, compression shorts with pockets and more trouser-related conundrums. If you want a chance to get expert advice from our team, send us an email at [email protected] with the subject “Ask the Strategist.” We’re here to help – and you may see your question answered in a future newsletter. 

“I can’t take it anymore. I’m five feet tall, have a big belly (legacy of my sweet nine-pound, 22-inch baby), and can’t find pants that fit. The closest I’ve come is Old Navy’s Petite Extra High Waisted in 12P, but I hate fast fashion, and they wore out after less than three months of regular wear. My dream pair have an inseam of 27 or under, fit the belly snugly, don’t sag in butt or gape in thighs, are ideally some kind of natural-ish fiber, and are under $150. Can you help me find them?” 

The eternal struggle to find a pair of pants is hard on everybody, but it’s even harder when you’re petite and/or plus size. But Big Bud Press Work Pants check every box you’ve asked for. I recommend all of the brand’s styles because its pants are offered in petite (25-inch inseam) and go up to a size 6XL, and I love the work pants the most because they can be dressed up or down and clock in at just $110. (Some styles are even currently on sale for $78.) They’re made of a sturdy, 100 percent cotton, and the fit is exactly what you want: No-stretch cotton twill that fits snugly around the belly, butt, and thighs with an elastic waistband for some additional flexibility and comfort around the waist and stomach. Plus, the Los Angeles–based company utilizes local, ethical manufacturing, so it’s basically the polar opposite of a fast-fashion brand. —Dominique Pariso, writer

“My almost-15-year-old daughter is staunchly ‘anti-girlie girl’ (her words): no leggings, no short-shorts, no flounces, no jeans, and definitely no skirts. Can you help us find some shorts that aren’t basketball shorts or matronly Bermudas? Bonus points for an elastic waist. Oh, and she’s a competitive swimmer so she has some serious muscle.”

You didn’t mention your daughter’s size or height, but I’m guessing that since she is 15 and muscular, she can likely pull off some women’s sizes. My first suggestion is this great pair of sweat shorts from Gap: elastic waist, generously cut in the legs, with a nice but non-flouncy dolphin-hem detail and pockets. They come in petite, regular, or tall sizes that are neither short-short nor matronly and four colors. Or, in Gap’s kids’ department, I found these pull-on crinkle gauze shorts that also have an elastic waist and a loose-cut leg that isn’t too short in sizes up to kids’ 14/16. (Be sure to click around the site a bit: There’s another product page that features a similar pair in more colors and a women’s version as well.)

If you want something that is non-basketball but still on the sportier side, I have my own “anti-girlie girl” daughter who likes the running and performance shorts at both Old Navy and Target for their loose, comfy cuts and elastic waists, as well as a range of color and pattern choices. Depending on your budget, I also highly recommend Athleta for nice-looking, size-inclusive, non-girlie, sports-friendly styles (though Athleta Girl tends to have shorter inseams than the women’s sizes). Try the Run Free, Trekkie North, Farallon, or Brooklyn styles. —Jen Trolio, senior editor

“I’m looking for sturdy, tapered or not too wide-legged black cotton, pants that can be part of a three-season uniform. Not wool or stretch or ponte work-pants type things, not utility pants, not cropped. Just super-simple ones that work for everything. Struggling to find this even though it seems obvious. Does anyone know of such magical pants?’”

Because these are going to be part of a uniform, I’m going to suggest making the investment in Eileen Fisher pants, which are ultracomfortable and uncomplicated. This pair is made from a nice Pima cotton. Uniqlo’s another reliable player in the pantscape — these are just $30. And though these Abercrombie pants are branded as an “ultra” wide-leg, they’re not so wide — and they’re on sale for $60. —Ambar Pardilla, writer 

“As a size-16 woman, I find it impossible to shop for jeans that are 2024-trendy. No way am I wearing low-rise, but is there a pair of baggy jeans that will actually look flattering on me, especially given that I’m five-foot-five with shorter legs (and don’t wear heels)?” 

First, it’s my duty to shamelessly plug our guide to the best plus-size jeans. I heard about the Hester Jean from Wray in my most recent update to the story. There’s a hidden band on the elastic waistline that can be buttoned tighter (or you could size up for something baggier). Old Navy has some good ones, including a balloon cut. Good American makes the Good 90s — “bomb-ass jeans” — though the inseam is longer, I think it’s worth getting them tailored. And Anthropologie’s Pilcro line has gotten better. I like the big cuffs on these looser straight-legs. —A.P.

“I’ve recently started hitting the gym again and specifically need a refresh of good compression shorts. I previously had some from Myles with a phone pocket, which I liked, but I feel as though that could be a bit taboo? Any other gym must-have suggestions would also be much appreciated.” 

I’m pro-phone pocket, especially if it’s on the thigh. It might feel like a contradiction, but the best compression shorts I’ve used have felt like they weren’t there; they need to provide support but not so much that they smush everything down there — it’s just uncomfortable and takes me out of the workout. There are a few compression shorts that fit this bill. I’ve been using these from Saxx for the past couple of years and I like how they offer a little extra support (with the pouch) but don’t have a death grip on my legs. I also like how I can wear them under liner-less gym shorts, too. For compression shorts to wear on their own, I prefer running half-tights. These ones from Tracksmith are awesome because they have grippy elastic bands around the thighs that prevent them from riding up, and they’re available with or without a liner. —Jeremy Rellosa, writer