I empathize with this question. In my teens, 20s and 30s I cared a lot about what "other people thought". The most beautiful part of turning 40 for me was watching that angst disappear.
I work in a conservative industry and have a closet full of navy/black/grey suits.
So when I'm looking for cycle clothes I gravitate to things that make me smile (dh has a Led Zep jersey). Especially as a new rider who is sometimes discouraged, I use anything as motivation to get on the bike more often (the socks pictured below are my absolute favorite).
I have a big chest, so I'm careful to avoid jersey designs that accentuate that in unpleasant ways, but other than that, if its useful, affordable and makes me smile, its a keeper (I just bought a cycling jacket on serious clearance at REI because it matches the colors of my bike - yikes!)
I have to be "serious" a lot of the time in my life. One of the things I've found I like about cycling is that I get to be a bit silly again -
And what I discovered after turning 40 is that "everybody else" is too busy worrying about themselves to give a hoot about what I'm doing...



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