1) Red hoop earrings, Claire's, $0.16 (Part of a 6 pack bought for a dollar)
2) Silver Tree of Life pendant on black cord, $6, Claire's
3) Black silk short sleeve blouse, $10, Banana Republic via eBay
4) White khakis with black pinstripes, $9 Banana Republic via eBay
5) Red peep toes, $5, East 5th via eBay
Holy cheapass, Batman, it's an eBay outfit! Had I actually deigned to pay full price, this outfit would've easily run me $175, if not more, as opposed to under $30. Life's too short for overpriced clothes, and the thought of paying $50 (or the more accurate $80 and up, for work slacks) is anathema to me.
I've had people ask me when in my life I started being a cheapass and how I honed my skills to find some of my better deals. The simple answer is that I wasn't given a choice on being a cheapass. My family was not exactly rolling in the dough as a kid. Most of the time, except for rare occasions and gifts from grandparents, my clothes came from the clearance rack and the thrift store.
My mother only cared about quality inasmuch as "How many kids can this go through being passed down to?" That meant it had to have decent stitching, minimal signs of wear, and a material that was kid proof (we wore a LOT of cotton.) Over the years, I've expanded my requirements on clothing to account for issues I've run into when my clothes didn't last: sewn on decorations instead of glued on, true embroidery instead or printed embroidery, and, if I can get my grimy little mitts on it, a true material pattern instead of the dot, stripe, etc just being printed on it. I'll get more into clothing quality signs at a later date (possibly this weekend.)
We also generally didn't have a huge amount of clothing, as my mom was big on a "dressed in the dark" closet (and we were poor with very little closet and dresser space.) The "dressed in the dark" closet was the predecessor to my "everything goes with everything" closet. Everything she bought us had to match or go with a large chunk of our clothes, enabling us to grab a shirt, grab a bottom, and look like it was a planned outfit. If most of our closet was in the laundry basket, we could still look like we put effort into our clothes. (Yes, I still maintain a simple wardrobe partially for that reason. I don't like doing laundry.)
I honed my skills through a lifetime of being a cheapass and learning from experience. Fuck, that shirt fell apart. What went wrong? What do I need to avoid? Wow, that just looks cheaply made, not buying that. Learning to sew and tailor went a long way to helping me determine piecing quality. Learning what materials had which properties helped as well. Mostly, though, it was trial and error.
That's not to say that if you're just starting on the cheapass curve, you're SOL. Hopefully, you're acquainted with my good friends Google, eBay, and Thrifting. If not, get to know them. Google can help determine if a brand or fabric is worth a damn. eBay and Thrifting mean never paying full price (unless you think it's worth it.) Reading this blog and asking Google can help you pinpoint marks or good or shoddy construction. So will trial and error, although I'll try to help you minimize that. While there is logic and science behind cheapassery, it's more closely related to an art. You don't hafta know what you're doing in the beginning, so long as you're trying.