Flashback Friday: J.Crew Fall Preview 1999

Back in middle school and high school, I was introduced to J.Crew. I’ve been shopping at J.Crew ever since the ’90s and loved their catalogs. They were a staple for classic chinos, button-down shirts and the softest tees. Looking back, the looks were pretty plain, but the quality was great. I was going for the Jerry Seinfeld/Ross Geller fits back then – nothing too flashy but definitely classy and timeless. 

It’s funny how baggy everything was – even for grown-up men, they wore their jeans, chinos and sweaters way too big. The late ’90s into the early ’00s was the peak of baggy fashion. Heading into the mid ’00s, we were reintroduced to skinny jeans and slimmer-fitting shirts.

Also looking back, it’s interesting that J.Crew lost a lot of their “preppy” spirit in this catalog. They got back to that when Mickey Drexler took over as CEO in 2003, and had some of their best years after that. I remember it well, since I worked at J.Crew from 2005 through 2010. 

I’ve since thrown out about 50-60 J.Crew catalogs that I had saved over the years, but I’m glad I kept a few like this one.