Other manufacturers may do this as well, but I've found some great compromise shoes at Merrell. The pair I'm wearing this winter have full suede uppers but feel as if I'm walking around in my stocking feet--no sense of shoe at all. There's no elevation and the sole is very flexible in all directions but there's just enough sole to cushion from heat/cold and sharp objects you're likely to encounter while walking.

In short, yes. VFF's are the classic example though not ideal for slogging through snow and perhaps a little too alternative. You can fairly easily find lots on other minimalist shoes, and a lot of it comes down to budget, and how you feel wearing them. I wear Merrell barefoot, as I have confidence and experience of them as a shoe company, you get the vibram sole, and it seemed to get positive reviews. I'm very happy with them, even if in some respects I'm still adjusting to actually walk and run in the best way. I'm looking forward to seeing how my new gore-tex version stand up to the snow up the road in Detroit this winter.

Flat shoes are a good start, but they still isolate you from the ground too much in my opinion. Having the flexibility, having the space to splay my toes, and having a sense of what's under my feet (although still a long way from actual barefoot) are all invaluable parts of allowing your body to function naturally. As with paleo diets, it's never quite the same trying to recreate the experience or benefits with something that was designed to do the exact opposite.

Last thing - although you don't want frostbite and I'm not really suggesting going barefoot all winter, there is something to be said for gradually giving your feet a chance to adjust to the cold. They used to manage alright after all.

shoes?

It doesn't get as cold in Seattle as it does in Chicago, but I've experimented with wearing VFFs with Injinji socks (toe socks) and that seems to work just fine in ~20* weather (but no rain). Also, there are these boots by Vivo which look pretty darned toasty: http://www.vivobarefoot.com/us/ladies/brooklyn-27.html

I second the recommendation for Merrell's barefoot line...I have two pair my self, the Trail Glove and Tough Glove and am seriously considering investing in the Gore-Tex barefoot offering this year as well...

I, too have been wearing Merrell toughs and trails. The thought of going back to conventional shoes is too awful to think about.

I'm thinking about a pair of these for those times when real boots are called for (without the cork footbed inserts):

http://shop.oetzi3300.com/otz1-troop-leather/troop-leather-1.html

I have heard of people wearing aqua shoes with very thick socks. Most aqua shoes just have a thin very flexible rubber sole. Just don't step in too many puddles.

I tried shoes from ZEM Gear but they don't run wide, and the shoes fit like socks, so that didn't work.

Edit: I forgot about diving booties. Have you seen the Blue Reef dive boots? They're meant to be worn on the ocean floor, so they're definitely water resistant and warm.

My best answer for dealing with the cold would be to get good thick toe-socks with something like Vibrams. Personally, I love my VFFs. While I've thought about experimenting with other kinds of minimalist shoes, nothing comes as close to barefooting for me. I find the whole experience liberating.

For what it is worth, some models of Vibrams, like the Treks, are warmer than others. Leather just seems to hold in heat better, but is still breathable in summer.

I'm hoping to purchase a pair of SoftStar moccasins soon (http://www.softstarshoes.com/). They've been around for a pretty long time and hand-make what are essentially modern versions of moccasins that would have been worn many thousands of years ago. You can get leather soles or choose from a couple of different thicknesses of Vibram soles. They have lots of color and style options.

i just got on this website, noticed your post and decided to add my 2c. I'm just learning about paleo in general but i also know about a concept called 'earthing' which is a means to induce the earth's healing energies into your body (earthing.com). Long story short, you can buy sandles/thongs that are 'earthed' which means your body still has electrical conductivity to the earth and much needed by the body. You can buy these and wear as normal and no one will even know! electrically speaking its the same as going barefoot. Look for earthing thongs or goto earthingoz.com.au where i bought mine.

Hope it helps.