I think it's always better to be overdressed than underdressed (undressed lies somewhere in the middle, depending on the occasion). I tend to stick to a more classic style anyway, which has luckily helped me avoid being either of these things so far in life!
Going to agree and say overdressed. Sometimes it's better to look like you put in too much effort instead of not enough. Plus, you never know whose eyes you can catch!
I'm a programmer/hacker, so definitely underdressed for me. I would wear a black hoodie, black khakis, and nice red and gold colored Lebron James 11's, every day, if I could. I like sports jackets, but that's as fancy as I'll get, and I don't consider that too fancy. One day, I hope to build very technologically enhanced, protective clothing, so that I have a personally designed clothing, that enhances my mobility, and life. Nothing flashy, not a superhero outfit, just something utilitarian, and that helps me look anonymous, and blend into crowds, and makes me not stand out, pretty much anywhere. Preferably with mobile power, and electricity.
So, not overdressed, but very tech-heavy.
I’m always overdressed! It’s so much easier to maybe remove jewelry or open a blouse to make it look more casual! I always have a pair of black heels in my car to dress up even more, if need be.
Overdressed. In some situations it may mean I'm undressed.
Brandie
I am mostly over dressed for any occasion
I prefer to be over dressed. Its far easier to dress down should the situation arise.
Overdressed, in fact I sometimes do this quite deliberately, it seems to work rather well.
Being the obnoxious bastard that I am I deliberately underdress when shopping in high end stores, for example if I'm shopping at Armani I walk in looking like I fell off a homemade raft. Without fail the high end stores have always treated me exceptionally well and provided outstanding service. Tried the same thing in other stores and I usually get tailed by store security.
I think that is why they invented the little black dress. You can glam it up or tone it down with some slap (or not), some jewellery (or not) and some heels (or not).
Never overdressed but dressed for the occasion. Maybe it’s my age or because I’ve always lived in small coastal communities, but I seldom find a need to get all dressed up. I’m usually in a casual summer dress, skirt or shorts. Regardless of the clothes though, I always pay attention to the details.. shoes, jewelry, hair and make up (accentuate not cover up).
I'm consistently OVERDRESSED compared to my peers. I'm almost ALWAYS in a dress or skirt and blouse because of my job. I'm almost ALWAYS in high heels. I'm almost ALWAYS wear nylons. When I fly, I'm ALWAYS dressed up. I guess I just don't mind being DRESSY compared to most people today.
It is socially safest to be overdressed
When I go out I am always overdressed and my wife corresponds . It works both ways . Just the simple removal of a jacket can make you look more casual if you should feel overdressed. I too see some couples were the lady has made an effort and probably spent, a good couple of hours in the bathroom , whilst the guy literally has just thrown a baggy T shirt and scruffy jeans, with shoes that are better seen in a gym. Its probably why I get some admiring looks and compliments from ladies of other couples .
I am my mother's daughter. She always would prefer to be over-dressed and so do I. I may only be in my forties but I hate, hate, hate the casual look gone crazy. When I go out with a guy I dress up for the date and I expect him to do the same.