Our healthy ancestors didn't dress the way that is fashionable in the West today. It is not that hard to wear a bathrobe at home, but I would risk being called "the Dude" in public. Any tips for public paleo clothing? I have found these expensive pants- some of which pass perfectly well as dress pants. They have remarkable mobility since they are designed for yoga. These shoes are stylish yet very minimal.
You could go for the ultra alternative look, which would be SO comfortable, breathable, lightweight, inexpensive and not restrictive at all, but could you get away with it in the office? Well, it is all a matter of personal opinion, I would say go for it, nothing sexier than a man in a skirt, after all (and very inexpensive to buy/make) and it would probably take the focus away from the vibram's/bare feet.
But on a serious note, it is not just the fashion that should be considered paleo, why not go for alternatives to mass-produced clothes by buying natural, organic fabrics (how about bamboo or hemp, both very breathable and easy to clean?), well made clothes (even tailor-made) and trying to avoid third-world produced goods (which also means less airmiles).
What about buying fabric using natural instead of synthetic dyes? More expensive yes, but I would consider this the more 'paleo' option. Do you have a friend who sews/is a dressmaker? Keep it local. If you could ask him/her to make some clothes for you, you could specify exactly what you want, buy good quality natural fabric and save money too (also you will be more careful with them if they have been lovingly made by a friend). Handmade clothes last infinitely longer than mass-produced ones, so you will need less of them and they can be adapted just for you i.e. stronger fabric at the knees, more roomier cut etc. Lastly, they can be easily mended when ripped or worn out, which saves on more resources. I think it is definitely worth it in the long run, even though you may think the initial outlay is expensive (you may be pleasantly surprised at how inexpensive hand made clothes can be).
Think about hand washing and/or natural detergents too, which will make the garments last longer - and is better for the environment.
You could make a 'fashionable' paleo statement using mass-produced, synthetic, high performance fabrics made in China, yes, it is not difficult by any means and you certainly will be comfortable, but I think it is just as paleo to consider the 'hidden' elements of the clothes such as: labour, supporting local crafts people, air miles, natural alternatives and making clothes last.
Thrift stores. Not exactly ancestral, but certainly in the paleo ethos of not contributing to stupid consumption. Even organic cotton and bamboo are agricultural products (let's not even speak of tech fabrics), and are rarely grown in a way that is authentically sustainable and builds the soil.
Plus, as others have said: more money for good food.
I can't believe that nobody has mentioned Utilikilts yet. I bought one last year and love it. Very comfortable, practical, and attractive. I wore it hiking and hunting quite a lot last fall; the cargo pockets will comfortably hold a ruffed grouse or a rabbit.
Blog post re hunting in a Utilikilt here: http://fearsclave.livejournal.com/871969.html
Manufacturer's site here: http://www.utilikilts.com/
Vibrams are of course the Paleoid's answer to the Hippy's Birkenstocks.
When I have to wear bifurcated legwear (i.e. trousers), I'm a huge fan of 5.11 tactical pants. Despite the manufacturer's law enforcement/military/Blackwater-wannabee marketing, the pants themselves have tons of pockets, are insanely practical, comfortable, sturdy, relatively inexpensive and come in some nice soft earth tones.
Here you go I LOL'd at that after the NYT article came out.
Otherwise, I think there are very good reasons to think evolutionarily about clothes. Your skin is evolved to breath and get sunlight. I personally avoid tight pants and since I am lucky enough to be a girl I wear skirts much of the time, which perhaps has been a contributer in lessening my problems with girly ailments. I also have traded a bra with an underwire for a more minimalist elastic bra. I really move and feel better without a heavy duty bra.
Women have borne the burnt of civilization's deforming clothes and shoes unfortunately, but skirts are one option we do have that men don't. Try looser pants or maybe even a kilt!
Your clothing has a lot less influence on your health than your food. If you have unlimited resources, then yes, $100 for comfortable slacks or $160 for minimalist shoes may be reasonable. My price points tend to be a bit lower. I look for the best combination of reasonable comfort, appearance, durability and price--which is not necessarily paleo. I did splurge on a pair of Vibrams, which I use for sprinting and water sports--I consider VFF's to be a sporting good, not really a wardrobe item. My tip for paleos on a budget is to minimize your clothing allowance, and save the money for the best food you can afford.
I just would like to add that this sort of transition takes time. I would love to have things like Thai fisherman's pants or similar things, a few tunics, perhaps a kilt. But a philosophy of clothing can still show in clothes now, as well as go into future buying choices -- like clothing being looser and more sustainably made. I also think it is best to get the most out of the clothes you have. Give stuff to charity or a thrift store eventually, but make the change gradual.
A sudden wardrobe change strikes me as both impractical and a little vain, both of which seem out-of-step with paleo, imo. These are all good ideas, but I'm wary of putting money toward clothing when I have clothes.
Just my two cents.