When I was a sailor in the US Navy, I had a uniform. Several, of course. Now that I'm a civilian sailor, I also have a defacto uniform. For me, my clothing has to be able to accomplish certain goals.
1) It has to be durable. I mean insanely durable. Able to stand up to paint, acetone, sun, salt, sharp objects, heat, cold, and being thrown into a ball.
2) It has to be inexpensive, to a point. I don't mind paying for quality, but I don't want to spend money on a company's advertising or "image".
3) It has to look somewhat normal in a social setting. Usually there's a pendulum swing between fashion and function, and I certainly start in the functional realm and try to make it somewhat fashionable. I don't look like I strolled off the cover of GQ, but I'm not in blue overalls wearing a beanie.
Starting off, I now rock the Dorfman Pacfic Men's Ultra Lightweight Safari Hat. It is
incredibly comfortable, light on the head, and keeps the sun at bay very well. It also looks slightly cowbow-ish, so you get a couple of points in the fashion category, although not so many that if you get it a little messed up you'll feel bad about it. It's also cheap at $20 - $30, so if you really mess it up you won't feel terrible if you have to buy a new one.
Next up are my Dickies Shorts (model 42283). These shorts form the core arsenal of my clothing line up. I ride my bike in them, work on the boat in them, sail in them, and go to dinner in them. They are an amazing product.
Coming in a little below the knee, crawling on your knees these have you covered, and sitting in a cockpit with the sun beating down on you, the tops of your knees are shielded.
For my upper body, I'll wear T-shirts when I'm working, with sunscreen on my arms. A good way to build up your T-shirt collection is to find shirts for sale from organizations you want to support (Obama 2008, ACLU, etc).
But when sailing, or spending a lot of time in the sun, I go with the
lightweight nylon shirts made from Columbia or REI. Essentially they're the same thing: long sleeve, lightweight, dries quick, and keeps the sun off you. These can get a little pricey ($30 - $60), so I try to avoid wearing them if I'm going to be doing disgusting work (teak caulking, etc).
As another bonus to these, they have a collar and are more formal than a T-shirt. So they can do double duty as a collared shirt if you need to clear into customs and things of that sort.
They may be popular to hate,
but my Crocs are a God send for me. They dry out instantly, provide rather secure footing (except for wet concrete in which case they become ice skates), are cheap ( $30 ), and make my feet happy and healthy.
They also cover your toes, so if you're on your knees working your toes don't get mangled like they do in flip flops. Also, they cover the primary horizontal surface of your foot from the sun, another benefit to sailing with them.
So there you go. Perhaps not the most fashionable items in the world, but for my money, they are the most durable and useful for a life at sea and in a boat yard.