What should I be wearing?

Not much of a welcome, but that is a very broad question. How do you currently dress? That and other information would help.

Whatever you do, dont be an older dude wearing clothes that are too tight. That's trouble waiting to happen.

Get stuff thats well tailored and fits, but leave the tight t-shirts at the store.

Here is where you should look to start, most if this stuff fits:

http://www.styleforum.net/showthread...60731&page=126


Here is an example of "fits" (courtesy Voxsartoria 2010):

Wearing fitted (slimmer fitting) clothes will accomplish your goal.

When I retire I'm going to dress like Norton I, Emperor of the United States.

Good God, don't send him to that fucking sewer of a thread. He'll be wearing leather bracelets, socks with fish on them, unbuttoned OCBDs, double monks, and he'll get arrested in the rest stop men's room for having a camera.

Wear real shoes with leather soles. No dress/walk/comfort hybrids. This will elevate your game above the average Retired Man-Boy.

Well fitting button down shirts and wool pants/khakis (basically grown up pants). Jackets are up to you, depending on climate and preference. I met a judge the other day and he looked fantastic in a suit. I would guess he was in his 50s or 60s. It would even be SF approved. He was wearing a 3 roll 2. Looked like it was tailored for him; probably was.

You should wear chukka boots.

For what you are looking for, John Smedley polos and some of the slimmer Bill's Khakis. The Smedleys you will have to get online but the pound is falling right now, so a good time to buy.Real shoes with leather soles. Chukkas would be good.
This forum is geared more towards mens dress clothing.

http://www.johnsmedley.com/

I find RL Polo shirts on sale to be the best quality before it gets too expensive to bother with. Can't get the "basics" on sale though. Then again, I like them because they come in custom fit. J. Crew polos are pretty nice, as are Banana Republics offerings. For a custom Polo there is tailorstore.com Haven't tried them personally as I'm very happy with RL custom fits.

As for pants. I bought some J Crew wool ones on sale. They're pretty nice. Flat front and slimmer, maybe more for the younger generation? Not sure on that. I also like the Baroni pants. Pretty slim, comes in pleats and flat, wool, good value imho.

But honestly, Dockers are pretty darn good. They hold up well and if you like how they fit, thats all that really matters. If your looking for wool pants though, there are better options.

Never heard of Belks. I do all my shopping online these days it seems. Nothing OTR fits me anyway so it has to go to the tailor or I have to buy MTM. Except for t-shirts and polos. I can get a decent fit off of some brands. Pants need to be hemmed anyway and don't always come in my size.

Try some brooks brothers slim fit shirts and the more mature J.Crew stuff. I don't know why Alan C mentioned chukkas, but they are cool casual shoes, especially in brown suede.

It was a joke that apparently fell flat. Although chukkas are great! As said above, it depends on what you're dressing for (business casual vs. boardroom vs. I'm retired and can wear anything I want). You should look through the What Are You Wearing thread at the top of the page and get ideas. Dress well, showing good taste, and your fitness will shine through. You don't want to do things to specifically highlight it, however. It will look like you're trying way too hard.