Try a button down shirt or two? They look nice. But of course, iron them before you wear them. I know a guy who doesn't iron his shirts and they look like wads of crumpled paper. And he looks cheap.

The problem with golf shirts is that they don't look good after around three washings.

A nice pair of shoes wouldn't hurt. Women spend a lot of money on their shoes, so a guy could splurge a hundred bucks on the one pair of shoes he wears all the time.

Briefs, my father wore boxers.
Flat tummy, pleated pants. Tummy-plain front. Clean shirts and t-shirts. Jewelry held to a minumum. Date night- starched shirt. Nice shoes shined. Look like you care for yourself. Look like you like yourself. Be sparing with the cologne. Nails neatly trimmed as well as hair particularly if wearing facial hair. If you are a mechanic or work hard with your hands, I understand.
I believe that each man needs to own a good looking dark suit. Jacket can be worn on its own as well as the pants. You never know when you might be asked to attend a function that requires a dark suit.
Okay, enought of this!!
Go Chargers!!

I concur with sugarmama and very much with Azalea but have one small change: I think boxer-briefs are the way to go. :-)

If you take your button-downs to the cleaners, they'll take care of the ironing. It's more expensive, but totally worth it.

What don't I like? It's not so much what he's wearing, it's how he wears it. If it doesn't fit at all or he looks like he really didn't even try, then I'm not thrilled. No one needs to be a model to look good or, as Azalea said, look like you like yourself.

Boxer briefs...definitely...*drool*

No t-shirts or running shoes (unless you're working out), and NEVER slashed jeans.
Wear anything else as long as you smell clean, and look neat. Oh yeah, and NO jewelery :-D

I think both boxers and briefs are nice...just depends on the bum, depends on the legs...go with what accentuates you the best. I am a definite fan of plain front pants, belly or no belly. Ben Stiller always wears plain front pants, and he is stylin'. I did his look...perhaps use him as your style mentor.

I agree with Rebecca: Stiller is stylin'.
(So much agreeing going on! Howard, you have the friendliest comments around.)

And whatever you wear, don't wear one of those big fat gold chain necklaces. Cheeeeeesy!

Boxers, for that hint of easy access.
A nice pair of jeans, a clean t-shirt, and a sport coat... classically edible.
If a suit is called for, a nice unexpected touch does the trick... a nontraditional collar, a handkerchief peeking out of the breast pocket, or a tie that, while different and unique, does NOT scream "circus clown!"
And I have to say, an untucked polo shirt is always a hotty item in my book. Tucked-in usually looks too "safe' or "junior high soccer coach out on parole."

BOXERS OR BOXER BRIEFS!! Briefs make men look like little boys or sleazy Euro-perverts. ;)

Incidentally, I, too, have a 3legged dog (missing a hind leg)... I've been inspired by today's television programming to try to start a Doggie Special Olympics. We're sure to have lots of talented tripods here in the south, don't you think?

No pleats. Ever. On anyone.

Really, if you mind that, you'll be fine.