HSS Writers Prompt: Favorite Pair of Jeans

The HSS team shares stories of their all-time favorite pairs of jeans

As Denim Month on HSS comes to a close, the team thought it apropos to share with you stories about our favorite pairs of jeans.

The truth is that everyone has some kind of special connection to a certain pair of jeans. And it’s hard to describe that connection. But we know what we feel and we know you’ve felt that too.

Brian Sacawa, Founder

It should come as no surprise to long-time HSS readers that my all-time favorite pair of jeans are my very first pair of A.P.C. New Standards. From the very first style post on HSS to recent editorial, you’ve seen them during the best of times and the worst – or most advanced – of times.

I actually hadn’t heard of A.P.C. until a friend of mine – the same friend who recommended looking into whether “style guy” was trademarked – mentioned to me that he had bought a pair of selvedge denim, which just so happened to be A.P.C.

Selvedge denim was new to me and I was excited to do it “right.” If you’ve ever bought a pair of A.P.C.s, you know that they come with an information card that gives you different “recipes” for how to care for/break them in. I chose the semi-extremist recipe, which has you wear them as long as possible without cleaning – for me that was nine months – and then soak them for their first cleaning.

Chris thought this was insane. I distinctly remember him expressing his disgust with this once when we were in the car together.

Once I made it through that initial break-period, I had them tailored – hemmed and tapered – and they quickly became a part of me and integral to my personal style. You can see them through the years if you scroll through the Style Guide archives. It’s kind of amazing to see how they’ve evolved over the years.

Rob McIver, Photographer

My all time favorite pair of jeans… That has to be a pair of Lucky brand boot cut button flies. They didn’t earn that stature instantaneously, but over time they were like slipping into a second skin.

Those jeans saw me through nights out with friends, first dates with my girlfriend (now wife), cool nights around a campfire staring up at the stars, backpacking around Switzerland, you name it and they were there.

Retiring them was long overdue, but it was difficult because of all the adventures we had together. They were great and just thinking of them for this little writing assignment has put a smile on my face.

Adam Lehman, Writer

I’ll readily admit that my favorite pair of jeans is almost a guilty pleasure. Whereas most menswear enthusiasts would be head over heels for a pair of crisp raws, or some high-end selvedge, my absolute top choice is Bonobos’ base-range light wash jeans.

The thing is, those jeans just fit me perfectly – which is a tough thing to find for a guy my size. I’ve tried the requisite entry-level raw/selvedge denim, but half the brands don’t make a size small enough for my scrawny waist, and the ones that did were either too pricey or were super limited on options as far as cut goes.

So when I got those suckers and they fit like a glove, I wore them as often as possible. Add to that a new job with a far more relaxed dress code and I quickly had that pair so broken in that the fit and feel was just too hard to beat.

Maybe down the road, with a few more Benjamins in my pocket to shop around, I’ll find a crisp pair of selvage with the perfect taper to take my jean game up to a whole new level, but for now I’m holding on to what I’ve got.

Robin West, Digital Strategy

I’ve actually been a “skinny” jean girl for just under 11 years and have gone through at least 50 pairs. Some had a bit more stretch, some a bit more relaxed and most actually from Levi’s.

The one thing that they all had in common is that they would get baggy knees and inch down more and more as the day goes on. Most of you have probably seen girls pulling up their jean waist not knowing why they are doing the “losing my pants dance”, but this is why.

Last November, I finally decided to try a high-waist version from Madewell and immediately fell in love, even though they were two times the price I’d been used to paying.

They were perfectly soft (if jeans have less than 98% cotton they can feel stiff), they fit like a glove, they were just the right wash to dress up or down and after 20+ wears they fit just as well as the first time I put them on.

And they stay in place! The fear of Madewell possibly not having them next season or changing the wash pushed me to buy the exact same pair again at the end of December. Now that I think about it, I should stock up on more…

Chris Sarangoulis, Contributing Editor, Whiskey & Cigars

My favorite pair of jeans come from an era about twelve years ago when boot cut bordering on bell bottoms was the thing. I had a pair of low rise, boot cut, button fly Levi’s. At the time, this trifecta of jean heaven could not be beat. They were so soft I could have gone jogging in them.

This pair was the first jeans I wore until they literally disintegrated. Towards the end of their life, they were assigned to painting duty.

I was hoping that a new trend for paint-splattered clothing would emerge so I could once again wear them with pride. As we know, this did not happen. (I’m still waiting!). However, their ultimate demise was a hole in the crotch.

Share the story of your all-time favorite pair of jeans in the comments.

Thanks for reading.

Stylishly Yours,

The HSS Team
He Spoke Style