The Virtue of Wearing Out Your Favorite things

Growing up in New England, I was raised in a family that, stereotypically, cherished thriftiness and a well-worn aesthetic. In a household of five boys, it was both economical and a practical imperative. That top image is a little before I showed up, but rest assured that I wore pretty much all of that gear at one point or another.

Handing down blue blazers, jeans and winter jackets, reusing sports gear, and viewing Christmas as the wonderful time of year when new socks and boxer shorts showed up was the rhythm of our sartorial life.

To be sure, we also had a fair amount of inherited everything around the house, from furniture to books and silver. We also had closets filled with interesting bits of old family garments. I still have my grandfather’s beautiful monogrammed top hat box – stunning thing. While in high school, I once found a heavy navy wool cardigan that had belonged to my great grandfather – amazing thing with toggle closures and a cool collar. I was in an “I’m cool because I’m sort of eclectic” phase, so I wore that sweater until it fell apart.

The shabbiness made that cardigan sort of cool, but in retrospect its demise was probably a good thing. Full of holes and beyond threadbare, that sweater was less vintage and more …….. ugly. Still, I loved it; both for the family connection and what I imagined it reflected in me: personal style, a bit of iconoclastic flair paired with academic vibes, sartorial rebelliousness, and a touch of Yankee stubbornness.

In terms of personal fashion, I’d say that description still holds for the most part. I’ve always had a pretty clear sense of style and never cared too much what was considered cool or “in.” I like what I like. If everyone else is wearing it, that doesn’t really influence me one way or the other. Equally important, if not more so, is that when I buy something, I expect to wear it to threads.

I like when my clothes get a little age in them. I could not wait for my Barbour jackets to get dirty and dull. I want things to look used and loved, worn and lived in. Not fake wear or aged, just not new looking.

While old isn’t always better than new, old typically has soul and personality that takes time and wear to develop. Learning from a young age that good clothes take time to pick out, often require a bit of thought and savings, and should last for a good long time, was invaluable. Good clothing does look and feel different and often, better.

By ‘good’ clothing I mean items that are thoughtfully designed, made well, and meant to last for a long time. We often associate dress clothing with these qualities – like a handmade suit or a long-loved topcoat – but it can be anything. Raleigh denim jeans. A pair of Ralph Lauren khakis. Rancourt camp moccasins. A great leather jacket with a story that you found a few years back on some trip. A favorite Frank Clegg bag that took 6 months to save for.

The key is to find things that move you, get stuck in your head or in your heart. Clothing you want to wear every day is special and different. And if you focus on finding those types of things, in time that will be most of what’s in your closet.