I know I've been harping a lot of you to really invest in certain pieces of clothing. I believe that spending the extra buck on a pair of nice shoes or a suit will likely save you a lot of headache and wasted dollars in the future. Not only will you get more wear out of these pieces, but you'll also feel better wearing them.
However, investing so much in every piece of your wardrobe can get expensive... real expensive. Truth is, I think there are some areas where you can actually save money, and still look/feel great.
Here's where I try and save money when purchasing clothing:
T-shirts: I don't think there's any reason to get fancy with T-shirts. I prefer button-up shirts in more dressier situations anyway. As long as your T-shirts are basic (no logos), and fit well to your body, you're good to go. I usually wear Calvin Klein from those 3 packs at Ross, and Banana Republic T-shirts when they go on sale for 40% off.
Sleepwear: No need to impress anyone with your sleepwear. Good news is, you can find some really comfortable and decent quality stuff out there for cheap; just head to your local Macys. Or I guess you could wear a suitjama.
Socks: No matter how nice your socks are, at some point you'll end up ripping holes through them due to natural wear and tear. Sure, some socks may feel better against your skin, but have you felt the Merona ones from Target? I think they're pretty decent, both in design and comfort. Best part? They're $2 each.
Swimwear: I usually get my swimwear from Target, JC Penney, or Old Navy. No problems so far, and I still get the occasional compliment.
Underwear: You'll be going through these as often as socks, so I think an inexpensive pair of Hanes boxer briefs from Walmart should do the trick just fine. Just make sure they fit snugly to your body and are comfortable.
Ties: Some ties are very nice, and it might make sense to spend the extra money on one or two solid staples. For everything else, I think you can get away with paying under $25 for a decent tie at your local Nordstrom Rack, Marshall's, or TJ Maxx.
Seasonal/trendy attire: There are some overtly trendy items out there that likely won't last for more than a single season. If you must take part in such trends, I say buy cheap, and think of those pieces as easily disposable.
Accessories: Apart from a nice watch, I think you should save on most accessories. Why get a fancy, bulky Prada wallet when a $10 stainless steel money clip will do? Do you really need fair-trade, rare-picked silk from the highlands of the Himalayas fabric for your pocket square? I don't think so. Want a nice tie bar? Go to thetiebar.com and get one for $15. Anyway, hope you get the point.
Henleys and long sleeve shirts: My henleys are generally from Old Navy or the Gap, and they've held up marvelously over the past few years. When the time comes to replace them, I won't care too much considering that I paid under $12 for each of them.
Now of course if you have the money, I think it's always best to buy quality clothing, which can come at a cost.
However, for the rest of us who don't swim in money, but are looking into purchasing a whole new wardrobe, the items above might be some good places to save a bit.