I could see plunking down the big bucks, which for a jersey, in my mind, is about $70 max, for a really special jersey either from a very special event (like LRRH) or group (Amici Veloci rulz!), or supporting a good cause or a favorite vendor/LBS/website (bikejournal.com), or even if it's a particularly lovely design (I've purchased a couple of pricey but beautiful sheebest and sugoi jerseys that I had yearned for mightily... from TE of course
).
Oh yeah, and I paid quite a bit (I forget what, but the price gave me pause!) for what became my absolute favorite jersey, a very fine merino wool solid blue WollyWarm jersey from Rivendell that I wear nearly nonstop from November thru April. I get so much use out of it, it is a bargain relatively speaking.
The rest of my jerseys are the el-cheepo solid color Performance and Supergo 2-for-$15 specials.



... from TE of course
).
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