Think Of The Whole Package: This is a complex topic, and it can’t be easily distilled into advice. But the general idea is to be truthful about how your dress interacts with your physical appearance and lifestyle. On the one hand, it’s always easier to dress according to your stereotype—a husky man can look great in workwear in a way that a very skinny person may not be able to pull off. At the same time, I love when people dress against people’s expectations: nerdy guys in black double riders, rebels in conservative tweeds, young people dressed like older people, older people dressed in a younger person’s fashions, masculine people in feminine clothes, feminine people in masculine clothes, etc. When it comes to style, recognize that you can’t convincingly adopt someone’s wardrobe any more than you can mimic their manner of speaking (again, to bring it back to language). Pay attention to how other people use language so you can broaden your horizons, but allow your use of language to be natural to you. Good taste ultimately reflects something about you.
Rely On People And Stores: Over the years, I’ve come to know a few people who have developed remarkably tasteful wardrobes in a short period of time. Without fail, it’s because they relied on people with good taste. Some relied on the right tailors or merchants. Others had the advice of trusted friends. Whenever I have a question about a watch, I turn to Greg Lellouche, Mark Cho, or David Lane. When I want to get an opinion on a fabric for a bespoke project, I ask George Wang. Recently, I was wondering if I should get my polo coat made with machine- or hand-finished lapels. Given the very trad style, I turned to Bruce Boyer for advice.
Over the last forty or fifty years, fashion has gone through what I’ve called The Great Uncoupling. Instead of going to clothiers such as J. Press or Brooks Brothers for their entire wardrobe, people now buy socks from sock companies, jeans from jean companies, and untuckable shirts from untuckable shirt companies. I think this is a terrible development. There’s real value in going to a store with a point of view and working with merchants (or tailors) who can guide you towards better choices. Be cautious about trying to do this on your own. Be wary of MTO shoe companies that will sell you expensive shoes according to whatever wild thing you imagined while on hallucinogenic drugs. Or group order projects where people design things by committee. Find people who can help guide you towards a more tasteful, coherent wardrobe, especially if you’re just learning to use clothes as language.
Buy And Experiment: Ultimately, you just have to buy things and experiment. If you want to know whether tassel loafers or military surplus pants work for you, you can only consume so much visual media before you buy a pair and see for yourself. Fortunately, it has never been easier to resell things, either directly through platforms such as eBay and Grailed, or by going through consignors such as LuxeSwap and Marrkt. Sample slowly and let your experience guide you. When wearing new things, try to see what you like or don’t like about the style, so you can refine your taste and choose better purchases in the future. I wrote a post for Put This On once about how to build a wardrobe that allows you to experiment. Embrace this as a fun, lifelong process.