My recommendation is to save up some money until you can afford several basics from reputable retailers.
Also, try to bargain hunt! I just lost enough weight to be able to shop in regular stores, and was able to pick up SEVERAL new pairs of pants, all very nice, at
www.macys.com for incredible prices.
As for specific brands/pieces, it depends on your style. I tend towards a more contemporary, yet off-beat look.
I've been picking up semi-dressy black slacks such as ones from Kenneth Cole and "dirty" denim jeans from DKNY (still trying to find some nice stuff from Diesel) at really nice prices. I tend to wear "dress" shirts (untucked, partially buttoned with the sleeves rolled up) with my jeans or slacks to go out on the town, but all I have to do is tuck in the shirt and roll down the sleeves for more formal occasions.
I'm not a "fashion whore" or obsessed with labels, but I've found that investing money in a well-made piece is exactly that--an investment. For years I purchased poorly made (but often expensive) "freak" or street punk clothing that fell apart in no time. Now, I know that I can spend slightly more (or even less, when I find good deals) on something from ExpressMen or a similar store, and have a well-made article of clothing that's going to last. However, price does not indicate quality.
As far as jewelry, I'm probably not the best person to ask. My personal style involves tons of bracelets, large polished steel tunnels in my ears, a nice stainless steel watch, a necklace, and multiple silver rings. Most people prefer to tone it down a little. But what's important is that it fits your style and attitude.
If there's any stores like TJ Maxx or Marshall's in your area, look there. You may have to do a little more work, but you can find nice stuff for much less money than in regular department stores and mall's.
To get ideas, try lurking around some style-oriented forums. I've recently joined up with the
www.menshealth.com Style Message Board, and the Style Forum, as well (
www.styleforum.net). Not all the advice on these sites is useful, and much of it is unrealistic as far as budget goes, but it does provide good sources for discounted merchandise.
And if you're feeling lucky, try Ebay. Although I just signed up for an account and haven't purchased anything there, I've seen lots of pieces from very reputable companies in my size (which is a hard one to find) for great prices. Just be aware of what you're buying, how much it's going to cost (including shipping and any other fees), and who you're buying from.
As for building a wardrobe, many people have mentioned getting things that are interchangeable. That's great advice!
Try things like:
Black slacks
Belts, one brown one black
Grey or Khaki slacks
A couple pairs of versatile, well-fitted jeans (something with a little class that you can wear places other than just bumming around)
Leather shoes: one pair brown, one pair black
T-shirts in solid, versatile colors such as black, grey, white and a few "accent" shirts in colors like maroon, green, etc.
A nice jacket that can be dressed up or down (such as a leather jacket, I prefer faux leather with simple, clean lines)
If you have the need, at least one suit and a couple of simple, versatile ties
Several long sleeve button-downs in solid colors that co-ordinate with your pants and undershirts.
These pieces can be interchanged for any situation from just hanging out, going on dates, working, or for more formal occasions just by changing what you pair together, and how you wear it.
Good luck!