10 things a well dressed guy might worry others think about him

We all know a brash guy who proudly says “well I just don’t care what anyone thinks about me.” And that’s fine. But it’s almost certainly false. Because humans are programmed to desire at least tacit approval and acceptance from other humans. It’s part of the reason why a lot of us put some effort into dressing well. It helps in that area. Yet that axe can swing both ways. Because being a human is hard. Here are ten thoughts that might run through a well dressed guy’s head. And know that it’s okay.

  1. I hope they don’t think I’m shallow.
  2. I hope they don’t think I’m arrogant.
  3. They must think I spend money foolishly.
  4. They must think I’m just dying to have them ask me about my clothes. Or my shoes. Or my watch. And I really, really would rather talk about anything else, and I know that’s the last thing they want to talk about too. Please, please let me think about something other than the weather. Don’t talk about the weather. NO YOU JUST MENTIONED THE WEATHER.
  5. I wonder if they think I think they’re underdressed. That I think everyone should dress just like me.
  6. They must think I’m a player.
  7. They must think I’m trying to compensate for being incapable. That I can’t do this. Even though I can.
  8. They must think I want to be the center of attention, even though all I want is to be respected enough to be acknowledged but mostly left alone.
  9. They must think I’m totally self absorbed, and don’t realize that the world can be a harsh, violent, terrible place, and that by simply being able to put on this (suit, shirt, pair of shoes) I’m luckier than 99.9% of all humans that have ever existed, past or present. And that fact sparks both immense gratitude as well as an overwhelming, paralyzing sense of shame and guilt. Like, who am I? Who do I think I am, to dress myself like this?
  10. I hope they don’t think I’m worried about what they think.

 

Joe

Recent Posts

Steal Alert: Spier & Mackay’s Up to 20% off October Sale

It's a smaller select items event, but it's a good selection. True wheelhouse/bestsellers. Shoes, suits,…

1 day ago

Newness News: Orient Kamasu GMT automatic dive watch

Orient's toothy diver just got a GMT addition. 

3 days ago

The Dappered Essentials Shop

Updated for Fall/Winter 2026. Cost-conscious building blocks of a well dressed wardrobe.

3 days ago

Style Scenario: The Football Tailgate/BBQ/Pub Watch (nothing over $100 edition)

Supporting your team without looking like the fan shop barfed on you. (And saving a…

4 days ago

In Review: Nordstrom Henrik Italian Wool Sportcoat (navy blazer)

In person with Nordstrom's foundation blazer from their own tailoring line. Ships and returns for…

4 days ago