6 Ill-Fitting Pants Tailored to Be Good Pants

“Did you lose a bunch of weight or something?”

I’m standing in front of our photographer Sabrina in a massive pair of khakis. I haven’t lost weight, but her question is fair, and it’s making me laugh. Why do I own these pants? The “high waist” is sagging around my hips, the hems are puddled on my feet, and my legs are swimming in fabric. At some point I’d personally ordered these, tried them on and, impossibly, thought, yes, these are correct.

We’re at a tailor in Tribeca called Shopboy (which I heard about from Gossamer founder Verena von Pfetten and read about in New York mag) and I’ve brought six pairs of pants for “possible” alterations. Over the course of trying them on, it’s become comically clear that my strategy of always sizing up—inspired, I’m certain, by an instance of weight gain in college that made everything in my closet tight—isn’t working. My clothes don’t look “slouchy,” they look like someone else’s. In some cases, they look like they belong to someone seven feet tall. What’s weirder is, until now, I hadn’t thought of these pants as ill-fitting. I’ve just cuffed them or belted them or ignored them and moved on, maintaining the ever-present idea that I need more pants, when the truth I just need more that fit.

Which brings me here, flanked by beloved Shopboy founders Desmond Brooks and Kendall Khanna, finally disabused of the idea that I need more instead of better. I’m here because I do have enough pants. Most people reading this probably do, too. So in honor of finding creative ways to consume less, I present to you: How to get six new pairs of pants from your own closet.

1. The Aforementioned “Oversized” Khakis

The Aforementioned “Oversized” Khakis

This before pic really had us laughing. They were on super-sale! I liked the detailing! I’ve been belting them like this, but mostly they’ve been sitting on my shelf not looking worth the effort. Per my annotations, Kendall took them in around the waist and down the leg, transforming them into the pair of high-waist utility khakis Bassike intended them to be. In terms of satisfaction, buttoning pants that fit your waist perfectly is on par with executing a complex Tetris move.

Conclusion: Taking something down a size is something most tailors can do easily, provided you’re not looking to entirely makeover the shape (although some tailors, like Shopboy, can do that too).

2. The Runs-Large Online Purchase

The Runs-Large Online Purchase

I loved these Ssōne jeans so much that I’d been rolling them at the waist so I could wear them (very cringe since the denim and tailoring are high quality). Because I liked the Japanese-inspired shape of the barrel leg, we decided to just take them in at the waist/butt area and leave the rest. Zipping these babies up and feeling them stay firmly above my hips was such a relief. I didn’t realize how much attention I’d been paying to their consistent droop. This new adjustment made the leg look more neat and streamlined, too.

Conclusion is obvious but: If you have pants you’re constantly pulling up, consider having a tailor take in the waist a bit. Not only will be more comfortable, they’ll fall how they were intended to.

3. The Over-Statement Pants

The Over-Statement Pants

I was more nervous about tailoring these Staud pants than any other, because I’m obsessed with them. But in reality, they were just a little too long for all my shoes, and the shape was a hair too dramatic for my style. So Kendall took some length off the bottom and pared back the flare a bit to make it more subtle and I’m over the stupid moon about it! I wish I had these pants in every color, which is the opposite of what this story is about.

Conclusion: If you have a pair of pants you love but rarely wear, perhaps ones that have a more retro shape, consider whether a small change or two could modernize them a bit and make them more wearable for you. And consider what shoes you want to wear them with—these lilac pants always looked great with no shoes, but never quite right with. Now they look nice with sneakers and loafers, which are the shoes I wear the most.

4. The Sample Sale Trousers

The Sample Sale Trousers

I bought these Lemaire trousers at a Creatures of Comfort sample sale and deluded myself into believing they fit perfectly because I loved them. In truth, the waist was falling down and I had to cuff them about four inches. But their cut and (thick) fabric are unlike anything I own, so I was eager to bring them into heavier rotation. Kendall took these in at the waist, through the leg, and at the bottom. A full-body makeover. I’m now wearing them as we speak and I feel like a kid on Christmas morning.

Conclusion: If you’re feeling feverish at a sample sale, add $50 to the price for tailoring and ask yourself if you still want them. If yes, go straight to the tailor afterward to avoid that awkward six-months-in-your-closet period.

5. The Absurdly Long Jeans

The Absurdly Long Jeans

I’m not mad about the puddle hem trend, but ultimately it doesn’t work with my tailored sense of style. I even think these Trave jeans look kind of cool with bare feet all long like this, but they look ridiculous with shoes. The after is much more practical! I might have left them a hair longer if I could do it again—it was hard to visualize their shape without the weight of the hem—but that element of surprise was kind of fun too. This feels like a different pair of jeans entirely.

Conclusion: Don’t forget you can always go shorter but not longer! Be prepared for a new shape if you’re taking a significant amount of length off.

6. The Too-Slouchy White Jeans

The Too-Slouchy White Jeans

Over the summer I wore these MM6 Margiela jeans, which I got from a Totokaelo sale, so much I felt panicky that I only had one pair (what’s wrong with me). But the relaxed shape that made me love them only worked with sandals and in beachy contexts, and even then it was still a bit much. Still, I was nervous to hand them over in case they lost their perfect slouchiness, so we were sure to only take them in around the waist and butt. And they turned out perfectly: fit to my waist without feeling too tight.

Conclusion: Tailoring something to fit you doesn’t mean it can’t still look oversized, if that’s what you’re after.

I felt spoiled walking out of Shopboy, and so much more satisfied than I would have had I just bought six new pairs of pants. Putting resources into the clothing I already have instead of accumulating more stuff I don’t technically need was refreshing. Good tailoring isn’t cheap—see Shopboy’s price breakdown here—but it’s an investment I can see paying off for years. If you’re prone to feeling like you have nothing to wear when you’re standing in front of a full closet, consider how to make what you’ve got work harder for you. You probably have more than you think.

Photos by Beth Sacca.

Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

More from Archive