A few years ago, inspired by a photo of Bruce Boyer and an old Mister Crew post, I bought my first hat. It was Lock & Company’s Rambler, a soft trilby that can be rolled up and subsequently stuffed into a pocket. The style is a little more modern and casual than traditional headwear, but upon receiving it, I wasn’t sure how it should be worn. Should it be tilted forward or back? To the side? Can I wear it without looking like a neckbeard? None of the online guides I found helped. No matter what I did, putting this foreign object on my head felt like I was wearing a neon-sign that invited ridicule.
Over the years, I’ve occasionally worn the hat out of necessity: when I’m running out the door and don’t have time to style my hair, or when the Teflon-treated, water-resistant wool promises to give protection from the rain. Eventually, I grew used to it. I can’t say I wear it as well as Bruce, but it no longer feels awkward or unusual. It is, simply, my hat.
Social psychologists call this the spotlight effect, which is our tendency to overestimate how much other people notice our actions or appearance. This peculiar anxiety is captured in the single most common question guys ask when they’re starting to build a better wardrobe: “how can I dress well without standing out?” Whether you’re in Rick Owens or Rubinacci, techwear or tailoring, there’s no way to wear anything exciting nowadays without, in some way, looking different from others. Among men who wear sport coats, no experience unites like having to hear someone ask: “why are you so dressed up?” (Tip: tell them you’re going to see your parole officer for a murder conviction. They’ll never ask you again).
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