I am no spring chicken but I play in a 90's band. I struggle with how to dress appropriately. I am too old to look young so wearing a baseball cap backwards is not a good look for me. I could dress like a Blues Brother but then I look like I am out of place. Sometimes I think the BBrother look will serve as a gimmick for people to remember the band. Sometimes I think just wearing jeans, a t-shirt and a baseball cap in the normal way would be best. Blend in with the other guys who are in their 30's. Let's just say I am closer to 60. Any advice for a conflicted brother bassist?
The biggest bugaboo around here is shorts, particularly cargo shorts. Baseball hats are widely disputed, with good argument being made that they are often a reasonable choice for players with male pattern baldness. I would aim for keeping it as simple as possible, you don't want to look like you are trying too hard. Go shopping with a woman in her twenties (or engage a clerk) and buy jeans that are NOT dad cut. Add a black shoe and black long sleeve or t-shirt and leave it at that.
Here's some reading material to get you started... Gig clothes? Lack of style How Important Is Appearance For A Bar Gig Cover Band? Band photos: DIY or Pro What are you guys wearing onstage these days? Costumed Cover Bands: Yay or Nay? Dressing alike - I feel like a Wiggles My thoughts: look like you're in a band. That would mean taking it up a notch from your ordinary street clothes, and look like you belong together. But don't push it to the point of absurdity; no need for overweight people to squeeze themselves into spandex or older people to dress like they're teenagers or anything. There are a gazillion bands out there that gig in jeans and tshirts. That's safe. It's also boring as hell. Find that balance where you look like you made an effort to look good, without looking like you're trying too hard. That's the trick. A lot of the time it's not a matter of going far out, so much as in the details. Fitted clothes rather than baggy shapelessness, a distinctive pair of shoes or belt, a jacket in an unusual fabric, a touch of jewelry at your neck or wrist, can make a lot of difference. Genre matters too. If you're playing country, you want a different look than if you're playing grunge or punk, obviously. Here's my favorite look for myself (I'll take any excuse to share this pic, I'm so vain)
One of the most rebel-rousing performers I ever saw. I saw him work a room of perhaps 2,000 to a fever pitch (Perkin's Palace, Pasadena CA, early 80s). And I had the pleasure of tackling him on the dace floor of The Roxy around the same time -- Psychedelic Jungle was the album being promoted -- when he did a stage dive during "The Crusher." He was very sweaty and had surprisingly small shoulders, I recall from our tussle... Hey, I'm getting misty now, too.
I also do not know how to dress for a performance. I'm in a metal band, but I only have two black t-shirts, and the sleeves are intact. I have short hair and no tattoos. I am totally lost. If necessary, I will default to my high school band uniform of black pants and a white button up shirt.
As far as the "dad cut" jeans - as a chunky 50-something guy when I get normal jeans in a size to fit my waist the legs are ridiculously baggy. I recently discovered Levi's 511 "Slim" fit jeans - you can get them in big waist sizes but the legs are slimmer (note - not "skinny jeans"!). They are tough to find in stores - I order direct from Levi's or JC Penney on-line. Lately I've been wearing a pair of black mid-top Converse Chuck Taylor All Stars. I have a pair of Vans I wear sometimes too.
I would definitely recommend against wearing a baseball cap. They're made for keeping the sun off your noggin & out of your eyes, so there's no reason to wear it indoors.
I see pics of a lot of older guys on here with expensive gear showing up to gigs in jeans, white sneakers and a band T-shirt... DO NOT DRESS LIKE THEM! That look when out of style before it came into style...