I never liked the books I could find on style for men. They always assumed that every man should dress like the one on the right. Which I would do on a job interview, but not to a friend's house, to a ball game, on a date (except my rehearsal dinner, but that's done now), or at almost any other time. How to look on an interview is worth knowing, but there's more to the question than that.
The best advice I knew was given verbally.
I. Decide what you want to look like
; pick a style, possibly based on catalogs:
(In order, these are Eddie Bauer, North Face, Brooks Brothers, Banana Republic, Stetson. Banana Republic has more styles than that, by the way.)
I could keep putting up pictures, but you get the point.
II. While you're deciding, be flexible. If it's different, of course it will feel strange; you won't like it at first. But if different were bad to you, you wouldn't be looking for a different style.
For example, I used to wear glasses like these on the left, and thought the ones on the right looked like some sort of geek-chic thing. Someone convinced me to go with those on the right. They look great, and I look less like Harry Potter, boy wizard.
III. Get a woman (or a man who knows his stuff) to help you pick out this new look, and don't dismiss her suggestions. Of course, some women won't be good at this, but many will.
...and these are my own ideas:
IV. Look for things you will actually wear. Maybe you're just not flashy enough for that article of clothing. Or maybe it would be great at the beach, but you rarely go. Or, more likely, it may be impractical to do the special care the article requires. Look over the care instructions: if you're like me, you'll go for "tumble dry" over "be prepared to iron this thing every time you wash it."
V. Go shopping someplace cheap for the look you've decided on. Or look through the sale rack. Or look online at eBay; they sell things by sizes, so it should work. Once you've got what you want in your mind, there's no need to pay top dollar.
There you go. Good luck!