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I buy most of my stuff discounted on Ebay or at places like TJ Maxx, etc. - but one of my best (pricier, for me anyway) investments was a pair of $80 J. Crew wool dress pants that I bought in 2002 (age 16) and still wear. Dad had thrown a pair of my wool Express pants in the dryer and ruined them, and since I couldn't find the same model anywhere (they were older and from Marshalls) I stuck it to him by finding what I thought was a pretty expensive, similar pair. Of course, in the long run I probably saved him quite a bit of money on all the other pairs of black pants I didn't buy again!
Other than those, my "investment pieces" include a Theory suit for conferences, some Tory Burch Eddie flats from Ebay, and a couple of Longchamp bags (though my current one badly needs replacing--bought it used and it's been with me for 2 years, so now it has holes in all 4 corners!)
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ΦPA:Friendship Rooted in Individuality
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