Best designed shoe  

Classic
Birkenstock sandal -- now made in China ("Betula") at half the price, of course. Good design then, good design now. My feet aren't happy in anything else. . .
So shoot me.

lucchesi spanish goat boot w/walking heel....
a lucchesi cowboy boot is one of the most magnificient looking soles for one's feet ever made. with a walking heel, which most rubes don't get (the riding heel is useless unless you ride), they are the most comfortable, durable and beautiful shoe you will ever own.
i can't speak to current quality of lucchesi. my two pair are over ten years old. i've heard they were bought out. find a used pair on ebay and resole and reheel them.

Vans
My choice is the Vans sk8-hi high tops. In my humble opinion they are the best all around skate boarding and walking shoe ever made and they look good too.

These are not
the kind of shoes you want to wear to walk the red carpet on your way to an award ceremony, but there are all these other circumstances in life where you can wear whatever is comfortable, ultra light, well ventilated, washable, anti-slip and on the market for a reasonable price. It is called "crocs" and it is only missing a re-cycle logo...
http://www.crocs.com/products/footwear/anatomy.jsp

Hmm
I'd try those -- I get grief for wearing open-toed sandals in the workshop. I note the copy says (of the sole) "does no pick up debris"; this is interesting, as my Birkenstocks readily accumulate the little cubes of smashed tempered glass seen all too frequently on today's city sidewalks. . .

Perfect
Clark's original desert boots in natural or black suede. Perfectly understated and functional.

~
the lucchesi sounds nice. I have two pairs of black boots with walking heels that I bought used at a thrift store (10 bucks a pair). I don't know how old they are, but they have written in marker replaced soles with a day and month in 1979 - I bought them in 2004! Apparently durable and also very comfortable. Very versatile in terms of where I can wear them - walking to class or biz-professional.
I also like grey sneakers. And slip ons. The right ones of course.
Speaking of, I bought two very comfortable looking pairs of sandals at banana republic (on sale) and they STILL haven't broken in and are STILL uncomfortable and I am upset as you can see. It is like the robbed the look of a comfy sandal but made them inentionally impractible and impossible to wear for a long time, god forbid more than one fashion season, so you have to buy new shoes. That is an exagerration I know, I could just have deformed feet that didn't work well with those sandals - but I doubt that.

Crocs all the way...
I have to go with Koen on this one. I wear my crocs all the time for as long as the weather allows me to. I tried them also for work, but my boss thought it not a nice sight, together with my suit. But as my work shoes come off, the crocs go on. They are so comfy and light that you never want to take them off again.

Justin Ropers
I think that the roper boots by Justin are a well designed shoe. I prefer them to be broken in (I haven't been able to pay for a new pair yet).
I think that they are very comfortable and can be dressed or or down. The only draw back is that you can't wear them with shorts.
I think I might have a bias though because I'm from Texas.

Geo. reminds
me that I wore nothing but desert boots (by various makers: Wolverine, then Clark and knock-offs, including black ones) in the late fifties and sixties -- I discovered them as a high-school student and was convinced that nothing else was right for me.. Low shoes seemed so. . .incomplete, somehow. A "natural" shoe. . .
Fashions (good ones ?) never disappear -- in men's clothing, at least.

Okay, Crocs interest me, but what model do you recommend...
Let's here from the Crocisti about which model they wear and prefer?

Boot, boots, boots, boots
1. It's been observed that guys (myself included) have a hard time letting go of the clothes they wore while in school. Tastes congeal early; witness my continued attachment to the Eames lounge chair and Laurel mushroom lamp that I admired but couldn't afford as a lad.
2. Like many items of civilian dress, the desert boot originated in the military. Is there room in this forum to explore the virtues and influences of mil-spec design on articles such as furniture and lighting? I'm thinking of, for instance:
--lack of ornament
--matte-finished surfaces
--strict functionalism
--tension between economy-of-means and robust durability...
Any thoughts about this non-aesthetic aesthetic?
http://wmspear.com/Bantam/recon.html

Beach for me
The crocs I wear are the Beach model. They are simply heavenly to wear. I must say though that the Islander model also looks quite interesting... never tried them though (yet..)

sure
Well we all know the effect the military (and war in general) had on midcentury design. There is of course the exploration of molded plywood from the Eameses and also Risom's chair made from canvas straps used with parachutes.
I think I heard that bell bottom jeans originated with the navy ... something about how they could fashion the wide legs into temporary flotation devices ... does this sound right?
As for the shoes I like:
desert boots
justin ropers (i am a southern boy myself. this is for the cowboy who detests ornamentation)
beatle boots
chuck taylors