Fashion Sense, Style

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You can start by having different pairs of pants. Buy them all the same brand if you want, but you can get different colors at least. Faded black anything does not look good. If you like wearing things forever, get some blue jeans, they look better and are considered "cooler" the older they are. You can even get away with holes in them, and people don't notice as much if you wear jeans every day. At least, that's what it's like where I live.

I doubt that it's possible to have any sort of personal style if one doesn't truly care about fashion. If you don't care, you're just faking it and following advice, you don't actually have style.

that almost perfectly describes my outfit today (even my airwalks are blue and white plaid)--except my jeans were flared (which i liked back in the 90s as well). i refuse to wear "skinny" jeans, they look ridiculous on anyone unless you're a cadaverous heroin addict with a hipster beard--scratch that, they look ridiculous on those people, too.

Great minds think alike.

As for skinny jeans....ugh. I hate tight-fitting clothing, which is exactly why I hate most "girl clothes." I don't get the appeal.

The 1995 thing - jeans, comfy t-shirt, plaid shirt - was my style til about '08. Though due to my wide/flat hobbit-style feet, I couldn't find trainers that didn't fall apart far too soon, so tended to DMs or otherwise solid boots.

At the end of '07 we moved somewhere new, so, previously not wanting to draw attention to myself that such a change of style otherwise might, I took that opportunity to go the shirt&tie/waistcoat/jacket/tweed/corduroy/moleskin/fedora route I'd long wanted to, planted by a mini-crush on one of my philosophy teachers at college who pulled off such a look very well. Then the rationalist/skeptic/brony/NiceGuy manchild bunch came along and sullied the fedora. The steampunk crowd have the derby/bowler covered, so I'm left with the homburg. Or fez.

Either way, it's lots of the same. Singular hat aside, four or five examples of basically the same garment that pretty much go fine whatever the combination.

Though that's if I go out. Around the house I favour the comfy t-shirt/jogging trousers/tatty cardigan/slippers thing.

Nope.

I still dress like it's 1995.

Baggy jeans, a flannel shirt, and canvas shoes.

there was a guy in one of my classes at uni who rocked this look (i think he even might have worn wing-tips ) that i had a crush on--though he matched his with a newsboy cap instead of a fedora. are newsboys not in fashion anymore? back then i sometimes wore a vintage beaver felt fedora (found it in a consignment shop in kensington market in toronto), myself. i still have the hat--but as you said, the look has been sullied.