Soon after I joined Styleforum, a member whose name I don’t recall recounted a story that went something like this: “I was invited to a grill-out and wore a RLBL sportcoat with an open-collar shirt. Some guy yelled out, telling me I was overdressed. What the heck was his problem? That guy sucked.”

For a long time, I felt exactly like him.

When I first started to learn about style and became more active on the forum, my interest in clothing bordered on obsession. I was reminiscing about those years with my brother the other night, noting, “Menswear and clothing was all I could talk about; I was probably insufferable.” His gracious reply: “You weren’t insufferable, but… you did develop a reputation.”

Me, wearing a sportcoat to the Star Wars premiere.

Those of us whose passion for clothes lies in the tailored world can have difficulty in deciding when to dress down—and also what that actually means. It’s hard particularly because tailoring has such a long and interesting history, embodies influences from different regions of the world, and is associated with famous and well-dressed people all throughout the last two centuries. Plus, being neck deep in Apparel Arts illustrations, Duke of Windsor photos and Vox Sartoria’s blog tends to change your perception of just what dressing casual actually is. “What do you mean, ‘dress down?’ I’m wearing a pink OCBD and wool tie!” I once exclaimed at a birthday party.

Me, in a pink OCBD and wool tie at party.

Since those heady days of excitement, I have learned a couple of valuable lessons:

First, always remember to play it cool. Have you ever met anyone who’s recently run a marathon? If you’re not sure, then you haven’t—because they’ll definitely let you know. Likewise, many who are starting off, dropping insane amounts of money on B&S deals, thrift finds, Yoox discounts, and/or every brand carried by No Man Walks Alone, are desperate to tell whoever they can about the workmanship, the design details, the barchetta pockets! But that just isn’t interesting to most people, and it can be a major turn-off for some. Learn to play it cool.

Second, I learned to be okay with not wearing a sportcoat everywhere. Primarily, the problem is the desire to express my own style: I love tailoring, it’s what makes me feel good, and so I want to wear it more often than not. Another part of the problem is that I kind of have to justify the expense of all these awesome clothes. If I’m not wearing them out and about, why do I own them? I didn’t buy them just to look at them on the hanger. 

Me, fitting right in.

While I support both points of view wholeheartedly, I did come to realize that there were times my clothing choices were a bit precious at best, and somewhat alienating to my friends at worst. Much as we may want to wear the clothes that make us happiest all the time, we do live in the real world, and it’s possible to be overdressed. The guy wearing a sport coat to the grill-out probably did look completely out of place. Just as we all shudder at the people walking the street permanently clad in gym shorts, so too can it look out-of-place to be sporting coat and tie at a baseball game. 

The other issue at stake is how your choice of clothing affects those around you. I’ve heard enough side comments over the years from my friends to make me realize they sometimes feel underdressed next to me. Not that any of them would tell me to stop dressing how I want, but I’ve become more cognizant of how the clothes I’m wearing might make them feel. And I choose to dress things a bit down if our planned activities call for it.

With all this in mind, what’s a StyFo dude to do? Here’s my answer to how you can still dress in such a way that you feel good even when you’ve decided you should dress things down: focus on the details. Wear a nice watch that you know is high quality, but which doesn’t call undue attention to itself. Wear a navy polo with a rakish cutaway self-collar à la Agnelli. Wear your trousers that have side tabs and the extended waist closure. You can take pleasure in these small details, but they won’t call undue attention to themselves, or to you. If someone does notice them, it’s an opportunity to share a bit of what makes your clothing (and your hobby) special (but play it cool!), and thereby snatch sartorial victory from the jaws of defeat.