It was an old boyfriend who turned on my love of the easy style of a menswear-style striped shirt. I knew Matthew during the two summers we worked together at Camp Kooch-i-ching, right on the border of Canada and Minnesota. He was from Ohio and had gone to boarding school at Deerfield and was fresh off of his first year at USC when we met. This was the ideal kind of love interest for me, as Los Angeles was safely far away from me in Boulder, which made it easier to face the competition from all those tall, gorgeous blonde girls from Denver who seemed to have it all figured out. I could say I had a boyfriend, but since we only spoke on the phone every two weeks or so, there was no way to really know for sure... AND I didn't actually have to hang out with him. My friend Cal and I were the only two young women on Deer Island, among who knows how many boys and their counselors. We spent the first two weeks of camp flirting a bit, and choosing which guys to focus our attention on. I went for preppy Matt, and Cal went for an older guy with a mustache whose name I can't recall. We would take the boat across Rainy Lake to the tiny town of International Falls, where we would drink Hamm's beer at that very specific kind of darkened bar with dartboards, a jukebox, stuffed fish on the wood-paneled walls... it was a lot of fun.
He then took his crew of young campers for a two-week canoe trip through the Boundary Waters and left me with a pile of his dirty shirts, asking me to get them laundered while he was gone. Naively, I was excited. "Oh wow. I feel so connected to him. He wants ME to wash his shirts!" On this remote island with barely any plumbing, I washed them the same way I did my own clothes, and while I remember neither the washtub or the detergent, I can remember putting them through a hand-crank wringer and drying them on a line. Can you believe it? When he returned, he nearly broke my heart with his utter confusion as to why I didn't just take them into town and drop them at the cleaners, where they would be not only washed but also pressed? I should have broken up with him right then. Connected? Come on... even pre-Enneagram he should have known I am a Type 3 Achiever and there was no way I was going to take them across the lake when I could surprise him by doing them myself. But if you knew the joy in feeding those Brooks Brothers stripes into the pair of rubber wringers and cranking away... I loved it. I had never taken much notice of my own father's shirts, which would have come from JCPenney and knowing my mother they would have been the "easiest care" available at the time. My brothers really only wore knit henleys and concert tees (think That 70s Show) and so my introduction to true prep style – which is what I think of whenever I see a striped shirt – came from that first summer in Northern Minnesota in 1979. The Preppy Handbook would come out the following year, and this set me up perfectly to devour it like everyone else at the time. If I'm honest, I was more in love with those shirts and the idea of his prep school past than I was with him. Matt who?
That is a long intro to the classic menswear stripe, but it's been almost 40 years and I am still in love. I wore them over and over again as my weekend uniform all throughout the 80s... I would buy the smallest size of the Brooks Brothers Classic Fit button-down and roll up the sleeves. I had red and blue and yellow and green stripes, but my favorite was the "fun shirt" that, true to its name, had alternating panels of all those stripes on the sleeves and pocket and collar. In searching for a photo for this post, I found dozens of pictures of myself in that shirt with stone-colored jeans. My association might be New England, but Sid would tell you that the real history of these is more Jermyn Street in London than the Andover Shop in Boston... in his eyes, Bowring Arundel and Turnbull & Asser made the quintessential ones. When we go to the fabric shows with our team, we flip through hundreds of swatches of striped shirting from the very best Italian mills. Thick, thin, banker, barcode, Bengal, awning, pencil, candy... there are endless variations of stripes, and while I really only care about the colors, everyone else on the team takes great interest in the almost-scientific categorization, and it is fun to listen to them go back and forth.
My own daughters wear the size-small men's shirts from Sid just as I did at their age... they are young and look fantastic in something oversized and slouchy. For me, I prefer the fit of the Ann shirts which are designed with a woman's body in mind. There is our aptly-named Boyfriend Shirt – long and lean with less fabric than a real men's shirt – and the Director Shirt, with a dramatic long hem in the back that covers your fanny. If you like a more defined waistline, our Tie Tunic is available right now in a super bold stripe and it is so so flattering. There is a quieter riff on the "fun shirt" I got so much mileage out of: our Mandarin Tunic in a few different stripes that run in different directions... less colorful and probably more wearable! It is made of one of my favorite fabrics, our compact cotton, which is very very thick and structured. My design team could talk to you all day long about why this is so special, but I just like the way it feels against my skin and holds its shape. On the opposite end of the tactile spectrum, there is this pair of striped popovers... soft in color AND in feel since they have cashmere mixed in. Dreamy.
The thing about a stripe is that it is so easy... the kind of pattern you don't need to think carefully about or 'know fashion' to pull off. It can add just a bit of pop anywhere – with plain blue jeans on the weekend or tailored trousers for a chic Gloria Steinem, I-can-wear-the-pants-in-the-family look for work. You can bohemian it up by adding a floral long skirt and leaning into the mismatch of patterns. You can button it up to the top and look nerdy-cool, or unbutton down as far as you dare. A striped collar or cuff looks great poking out of a sweater in cold weather, too. When I travel in the winter I wear lots of solid turtlenecks – but I always include one striped shirt at least to cheer me up when I am bored of the solid repeat. I love a patterned scarf mixed with it as well – maybe a little paisley one tied at the neck and it will look very Carnaby Street. I suppose I have made my point by now... boyfriend silhouette or boyfriend memories aside, you need a stripe or four in your closet, I promise.