The unenlightened might say that crossing the finish line 37th is losing.
The wise ones observe you at the start line and know you’ve already won.
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I exist mostly off hand-me-downs, so perfectly matching kit is an anomaly for me 
I dig the mismatched socks thing though. I’m also kind of a backwards triathlete and prefer crew socks for running, though short-course racing has imbued me with a pathological disregard for gloves on shorter rides (which I do not necessarily recommend)
Some other heinous opinions;
- all neons match, but rarely with colours that are not neon.
- sunglasses need not match, but it looks more deliberate if you have really obnoxious ones.
- looking cool is for recovery rides. Hard rides are all about testing the limits of social convention.
- your team kit is dumb.
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I am embarrassed for many of you. Here are the rules, break them at your own risk.
- White shoes, the whiter the better
- White, aero socks, no trim, no logos
- Black bib tights. period. Cycling club shorts and jersey an exception.
- Basically any jersey you want that doesn’t have a ridiculous saying on it
- White helmet.
- Sunglasses over strap (in case you fall)
- Bar tape to match saddle.
- White, or black bottles ( must be identical)
Whew, glad I cleared that up for everyone. And as you can readily see, I have all the kit and ride like sh$&!
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There are certain, very specific cases where your jersey colour doesn’t have to work with the rest of your kit & bike.
Wear baggy shorts with your cycling jersey
Come on, that stem isn’t even slammed 
@Trackdom this thread is TIC…but if you are really asking, the key to group rides is have fun, be safe, be friendly, learn the group etiquette and enjoy the post ride coffee.
@Power13 maybe black socks were in the mountain scene but, no one cares about mountain bike fashion 'cause there it all looks bad. 
LA brought black socks to the pro peloton for sure IIRC. Correct me if I’m wrong…
On the topic of this thread all I have to say is nothing, and I mean nothing looks good on old people with wrinkly legs. I’m getting old and my skin is starting to lose elasticity too. When I look in the mirror I just shake my head. This has to be one of the reasons old guys are pissed off and grumpy—> 
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I figured as much but as a new cyclist i struggled to work out the serious from the not.
I think i’m following along now 
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You will run into snobs on the road or trails just like everywhere in life. Just remember to the general public we all looks absolutely ridiculous Haha. Enjoy the journey. Lot’s of great people riding so don’t let the haters get you down. They are just unhappy with themselves most likely.
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You only look ridiculous if your water bottles are mismatched.
Snobs will be snobs. But the rules are the rules.
(This is the thread I never knew I needed. With all the talk of how to estimate LT1 without a lactate monitor; the appropriate amount of Z2, polarized, pyramidal, base, build, recovery, sleep, blah, blah, blah … it’s about time we talked about the important stuff. Like curated tan lines, mid-calf socks that accent the jersey, black bibs.)
Look like a champion, play like a champion🤘
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I wear a cycling cap while running, so as to wind up both sides of the aisle.
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I have been known to ride in a tank top and hip bag in lieu of a proper jersey from time to time.
I mean, Sun’s out, guns out.
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Look pro, ride slow.
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My water bottles are always mismatched!
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As long as you have good legs.
(Not actual good legs, just good looking legs)
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Matching water bottles are table stakes. For a truly pro look, they should also display the brand of your energy drink. These are mine.
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I want to respond to this, but my 2023 resolution is to only interact with people who put positive energy into the universe. You are clearly not one of these people, and an agent of chaos.
True story: I went on a ride with my brother-in-law a few years ago, and we stopped at the top of a very photogenic climb to take a picture of our bikes against a beautiful backdrop. I, obviously, removed my water bottles for the photo — everybody knows to do this. He, to my incredible dismay, not only had mismatched bottles … but he left them mounted for the photo.
Later when he posted the picture to social media I had to politely, but insistently, request he edit the photo so as to not include my bike and remove the @ mention of me. I have a reputation, and It was put it at risk by merely riding with him … the social media celebration of shabby aesthetic was a bridge too far.
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Not many outside Chicago are gonna get that….but I definitely need to find a couple of those bottles!!
(Lol … Malört!)
I’m sure you are cultured and well-mannered enough to only mount those when on a gravel bike, or an All-City steel rig with an appropriate (and necessary) handlebar bag w/optional growler cage on your fork.
I’m also sure you have a moustache. If not, you need one.
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I wear one walking my dogs. How many people does that wind up 
Actually cycling caps, especially the cold weather, are perfect for dog walking
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