When I started cycling, I wore a t shirt or an inexpensive technical t shirt - eventually over bike shorts. I used to joke I was in the "t-shirt club" and I wasn't one of the "cool kids". I didn't understand why a jersey was worth buying, although I did get that the shorts were a good investment.

2+ years later, I love the functionality of bike clothes. I don't ever look at someone else and think about the clothes/ fit if they are carrying extra pounds. Speaking as someone who has worked hard with my bike to lose weight, I just think it's great that they are out on their bikes. I sometimes cringe at the fat roll that just won't melt off my midsection, wish that jerseys were more flattering to my bust, and envy women who actually look great in a jersey and shorts.

I understand for long rides, shorts and the other cycling paraphanalia are probably the best solution. The bright colors do make us more visible, and yes, I LOVE the pockets in the jerseys. Wish more shorts had a little side pocket for few bucks or a key though. I am at the point where I find cycling clothes attractive- and tease my DH that I like the view better when he wears the regular shorts and not the mountain bike shorts....

Like any activity that has specialized clothing - I think you get used to the look over time.