They make "women's" bikes that look like men's frames -- rather than the step through kind we sort of traditionally think of as ladies bikes. A bike shop can help you with this!
Sounds neat! I haven't done anything like this either, but have been trying to talk my DH into something of this sort too. We would have new bikes to buy and lots of training to do too -- our leaning toward mountain hybrids wouldn't be comfy for a big ride!
I'm not sure what you mean by reg ankle socks -- here's what I've found, and yes, both DH and I have wide feet. I have found that the thin, kinda spendy seeming socks like those we find here on the team estrogen web site are really helpful. My feet don't get all sweaty, and there's more room in the shoes.
Shoes -- I have some Specialized Taho shoes that I've found work well for me. They were around $70, which is a bit above your price range, but here's the thing: I have wide feet. That makes it hard to find shoes to begin with, as you know. These lace up, so they're nice and adjustable. I did have to buy some longer laces than what came in them. I also took off the velcro strap, cuz I didn't like it. The soles of regular shoes didn't give my feet enough support on pedals, and my feet hurt until they went numb while riding, then they hurt after riding from being uncomfortable. My riding performance and comfort greatly improved when I got the bike shoes even before I got pedals and those little metal cleats in the shoes.
Remember that sun is an issue even on cool cloudy days. I like a bit of a sleeve -- especially if you're wearing that camelback! Something I found with bras: if I wear the compression sports bra, things are smashed together and get heat rash. I am much more comfortable in a bra that separates the girls!
From what I read here, opinions vary a lot with one exception: find a bike short with the padding that you love! We'll all surely agree that an unhappy bottom makes a miserable rider! One of the things I've discovered -- I've got a couple of pair of shorts that I found at REI for about $20/pair, and they were okay for me when we were riding ten miles and maybe okay for 20 miles, but above that and they just weren't enough. I've got some in the $60 range that feel much better when I put in a longer day on my bike!
To add to this, you could go through a few seats this summer finding one that feels comfy. This is an important process -- again, when your butt hurts, there's no way to enjoy riding for any kind of distance!
I'm still fairly new to riding, having just one season under my belt. I'm itching for the weather to warm up (just can't coax myself to ride in my parka) The stuff I've written here are things I've learned so far from trial and error and these wonderful ladies!
Karen in Boise




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