I figure my body only touches my bike in three places: my hands, my butt, and my feet. Therefore, I don't skimp on gloves, shorts, or shoes.
I've found the brand and model of shorts that I like and I buy one pair each year, which even at $100 I can justify. I have quite a collection now. When the old ones get saggy after about 5 years, I put them in the winter shorts drawer and only wear them in the winter under tights. The tights keep things, well, tight. Even when they get some holes in them, I can still wear them in the winter under tights.
I guess I'd get rid of them when the chamois wears out, but that hasn't happened yet.
DDH, check on Team Estrogen's website. They have alot of clothes for hard-to-fit women.



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