Not really… I have several coworkers whose dresses and jewelry are spiffier than mine but who totally manage to screw it up. Varicose veins do not go with anything, they rather spoil whatever you’re wearing.
By leaving out that pantyhose, they’re turning their spiffy getup into “I’m blind, by the way”.
If I met a man wearing an overcoat and smoking a pipe, who introduced himself with, “Dr. X. XXXXX, working in ZZZZ departments, but you can call me X,” I would fall in love instantly.
Just think of attire as social camoflage, and dress to fit in with whichever social group and activity it is that you want to be apart of.
I would add a third category: The Statement Makers.
You know, the college student types (who sometimes turn into adults making the same statement) who insist that dressing up is wasteful and ridiculous and old-fashioned and “just don’t get it” because people who do it must be trying way too hard to impress people. I went through this stage - ripped jeans, flannel shirts that looked dirty even when clean - and enjoyed my self-righteousness while it lasted. Then I joined the workforce and worked in an office where I was required to wear skirts and stockings. Even when that restriction was no longer in place, I felt better wearing nicer clothes.
I can understand comfort. I usually dress for comfort, too. But most of my comfort clothes are still pretty decent, so I don’t have to think a whole lot when I put on an outfit. If they’re comfortable and decent and basic (think casual khaki pants, a tailored T and clean shoes), I can literally just throw something on, put my hair up and leave without feeling sloppy. Most of my work clothes are also comfortable, but made of slightly less functional (though no less comfortable or washable) material and more likely to include a nice sweater or tailored button down.
Anyway, I digress. To the OP: I think most people have a certain type of clothing they’re comfortable with, for whatever reason, whether it’s because they’re trying to project a certain image, hide something or feel better about themselves. As long as you’re comfortable in what you’re wearing, whatever your reasons, don’t sweat it. People are usually more concerned with themselves than other people anyway. Unless you’re walking down the street in a tutu, they probably won’t notice or think twice about it.
Ru Paul: “We’re all born naked. Everything else is drag.”
Yeah, but it still tends to read as more dressy. Work involved doesn’t have jack to do with formality–pulling a sundress over your head and zipping it up is every bit as much work as stepping into a ballgown and zipping it up, ya know? Dresses just read more…dressy…than pants of roughly equal formality. It’s just a perception issue. My pet theory is that it goes back a few generations to when pants were acceptable for when you were doing housework or working in a factory, but simply Not Done for social interaction. It’s changing, the same way the “hose is dressier than bare legs” thing has mostly changed, but slowly.
Got a thing for smooth-talking petty grifters, eh?