I started off with cheap stuff and found it was much better than my old gym shorts and underwear and the jersey wicked sweat far better than that cotton t-shirt. Later, I tried bibs and wondered why anyone would ever wear anything else.
Taking advantage of sales, I was able to try more expensive brands and found that yes, they did feel and fit better to me. If anyone is wondering what the fuss is about with expensive kit, just be on the lookout for sales at the end of the season.
Now, I'm at the high-end Castelli, Assos-on-sale level and having a blast riding my bike. I have no desire to go higher but if I was riding more often and/or had more disposable income, I might be inclined to give some of the pricier kit a try.
I prefer wool base layers when it gets colder; absolutely love my Castelli Gabba jersey with a wool base layer and arm warmers. That gets me through most of the brutal winters we suffer down here in Alabama.
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As for style and color, I wear what I like. Pro team jerseys and bright colors. Except the shorts have to be black.