At the back end of 2021, I yearned for a sweatpant that was baggy and would drape nicely over a pair Jordan 1's or Timberland boots but also had a nice tailored sort of finish to them. Not long after that we launched them in 2022. Fast forward to today, and it is one of our best-selling sweatpants. I have even made them in leather, as well as knitted mohair and cashmere (yet to be released but available for pre-order in-store at our new Beverly Center flagship for your viewing pleasure). They were even the base for our also yet to be released baggy cargos and baggy jeans that I hope we can drop soon.

What I like about these is that they are both dressy and casual, and I feel just as comfortable wearing these on a date night with a pair of Timberlands as I do rocking them casually with a pair of slides or our High Top Roamers. I like how it gives you good shoe coverage with a pop of shoe at the toe. With a few more iterations in the works, it is clear to me that the Bootcut Sweatpant will be a staple in our lineup of sweats and pants for the foreseeable future, as it offers a different look and fit that you don’t get in the Roaming Sweats or Surplus Sweatpants. The Y2K bug is back to some degree, maybe a large degree, and I am definitely here for it. Those awkward teenage years of mine back in the early 2000's can now be revitalized in a new and modern take on it and way less awkward.

Shop the Bootcut Sweatpants.