Who do you dress for?

You didn't include "for the occasion" as a choice. Sometimes it's appropriate to be comfortable or whimsical, sometimes you want to make a specific impression, other times you need to give people what they expect in the circumstances.

I'm a consultant so I'm always selling myself. My selling point is that I have something special to offer and am not just an interchangeable body, so I have to look right without looking the same as everyone else. When I have a gig at a government office I dress "casual" like they do, but in my own fashion. A dress shirt but one with some colors, generic pants, whimsical socks, but always wingtip shoes because I've always liked them. At a corporate office I'm more likely to wear a tie, but again I have my own stash (of about 100 that I've collected over the decades) which tends toward the very un-conservative. Maybe slacks instead of Dockers, and less outrageous socks with my wingtips.

But if I'm teaching, I want to project a professorial image so they unconsciously see me as an invited elder with something valuable to share, rather than someone they need to defeat in an argument because I invaded their territory. So I wear a tie and a sport coat or a suit, but with an eccentric look that shows I'm not part of "the Establishment" but still the same old hippie I was forty years ago... but with a better job and more money because I'm really good at what I do and they'd do well to pay attention.

When I play my bass guitar on the weekends I'm a full-spectrum entertainer and the way I look is part of the performance. I hate it when I spend money to see a band play live and they wear jeans and sneakers--even a dance band that plays other people's songs. Depending on the venue and the music I might wear something retro like a narrow 80's tie with a piano keyboard or one of my concert souvenir t-shirts like Roxy Music. I also have a sweatshirt my wife had custom-painted for me when I was president of the teddy bear collectors' club, a teddy bear playing a bass guitar. Most bassists are rather quiet so I go the other way. I even have a six-foot long stocking cap that looks like something from a Dr. Seuss book that I wrap around myself in creative ways at winter gigs.

When I go out dancing I "dress up" but from my own generation, dress shirt and tie. I have a red tie with a black panther subtly emerging from it with red eyes and I wear that with a black or red shirt. Also a wide assortment of whimsey, including Betty Boop and a couple of Escher designs, and I love purple.

If I'm just going to the store I don't put on airs and just try to look decent with clean clothes and combed hair. Jeans and boots in the winter, shorts and sandals in the summer, and one of my bottomless drawer of rock and roll t-shirts. If I'm staying home I'll wear sweats and slippers in the winter and shorts and bare feet in the summer.

My wardrobe choices tend to match my wife's pretty easily, and after thirty years together a lot of my clothes are ones she found for me, although she seldom urges me to buy something I don't want. She's very good at picking out the more formal stuff like suits, without looking too conservative. She has a better eye for color and makes sure I don't pick a color that I like but makes my skin look like a wilted vegetable in contrast.

Yes, and men and women don't have the same taste. If you ever get up into the stratosphere of the corporate world, you don't dare let your wife dress you for work. Men who are movers and shakers do not like the kinds of men's clothes that women pick out.

You're just full of surprises. That's not an attitude that would go over in my crowd. My wife is content to make women jealous by communicating with them directly, stepping out of her Mercedes wearing a five-carat ruby.

Yes and no, but the nude body whose image we see is heavily influenced by the clothes. The cut and pattern of your clothes direct the eye to specific areas of your body that you want us to concentrate on, and the geometry creates an optical illusion of a shape that's not really there. You can tell how intensely a woman is working her clothes by whether she turns the light off before or after undressing.

Another professional speaks out. Whether you like it or not, your clothes are communicating. You're wise to understand what they're saying, and even wiser to choose their statement. It doesn't have to be conventional or popular, but it should be something you want people to associate with you and not just something that looked nice lying in the drawer. Whether the "opportunity" you'd like to be afforded is a job, a position on the team, or a night out.

I wear (men's) silk undies from WinterSilks.com. It's a nice fabric that's comfortable to wear, and it's very long-lasting so I get my money's worth. And they come in some of my favorite colors, like purple.

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There's something deeply disturbing about you.

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As for the question in the OP and title. I dress for myself and convenience really. If going out with kids, dark clothes, etc.

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So you're describing your effects on people to that of bad seafood?

Okay.