The Levi’s That (Finally) Made Me a Boot-Cut Convert

This is an edition of the newsletter Pulling Weeds With Chris Black, in which the columnist weighs in on hot topics in culture. Sign up here to get it in your inbox every Thursday.Yesterday I was talking to Jason Stewart, my How Long Gone co-host, about my distaste for linen. The wrinkles are, of course, a problem, but my real issue is handfeel; I need a more substantial fabric, especially for pants. Which doesn’t mean 12-ounce ring-spun or firm cotton duck canvas, especially in August, but something slightly more rugged just feels more comfortable. I don’t wear sweatpants outside, no matter how expensive or well-fitting; I find them great for puttering around the house in the winter months or maybe the gym commute, but at the airport or coffee shop I just can’t pull them off. A great pair of chinos is a smart compromise, but denim has always been the sweet spot.We are living through an awful age of “jorts”—oversized, unsightly denim shorts being worn by men and women of all ages. I am old enough to have worn JNCO jeans in high school; I looked like an idiot, just like most jorts-wearers over the age of 21 in 2026. Giant jeans are having their last gasp in the trend cycle, but these abysmal shorts are keeping the dream alive for some. Many outlets are reporting the return to skinny jeans; I pray we land on something more wearable than the Hedi boy pin-leg skin-tight dark washes or a return of the Cheap Monday skin huggers that I paired with black leather Repettos in the haylcon days of vodka sodas, cocaine, and 4-piece British rock bands that all sounded the same, no matter what NME said. This is all top of mind because I recently stepped out of my comfort zone and went vintage jean shopping in Los Angeles.I am traditionally a vintage Levi’s 501 or 505 guy. The 501 features a classic button fly and a slightly higher rise, while the 505 features a convenient zip fly and a mid-rise. The fits on me are slightly different; the fly closure is the biggest difference, a detail I am not that concerned with. When we made jeans for Hanover, the 501 was the north star; we made the leg hole just slightly wider, and I think we nailed it; I wear them all the time in a black wash. As soon as we landed in Los Angeles, I checked the hours of Denim Revival, a well-loved store for jeans and repairs on 3rd Street in West Hollywood. I was in the market for something different, specifically the Levi’s 517, a jean I had seen worn by my wispier friends; they sit higher on the waist and have a “boot cut,” a term that scared me. I wear boots pretty often, but I am mostly in Converse All-Stars, JM Weston penny loafers, or Belgians; nobody’s going to mistake me for a Taylor Sheridan show extra. When I hear the term “boot cut,” I immediately think of “flare” and picture myself stuffed into a 517, trying to look like a Led Zeppelin groupie.I went into Denim Revival right when they opened on a Saturday morning and explained my goals and fears to the staff. They pulled out a nice stack of jeans in a size 38 waist for me to try. Vintage sizing is ridiculous, but being handed 38s triggered me as a former fat guy who is now solidly a 34, but I trust the experts. My method is to scan them all for the best washes, then try them on in order from best to worst. I went into the dressing room and got going but nothing was tickling my fancy, and everything felt a little too big. The salesperson said I should try a 36; a gentleman who seemed in charge chimed in from behind the cash wrap, saying he didn’t think I would like them, that the flare I was nervous about would seem even more extreme.I took my new stack and the first pair I slid on was the perfect color and fit like a glove. I put on my shoes and went out to ogle myself in the public mirror, and this pair of 517s did exactly what I wanted. The boot cut was so slight that they seemed more like straight-leg, and, most importantly, they fell perfectly over my shoes. Everyone agreed these were the ones; the boss admitted defeat and graciously gave him a 10% discount to show that he wasn’t a sore loser. Trying on clothes is something I find no joy in, but that day was efficient and successful, and I found a whole new Levi’s style to relentlessly pursue on eBay. But it was also a reminder that doing business IRL is superior, and specialty stores like Denim Revival might charge a little more, but the personal touch is worth it.