I am in the same boat as KSig RC and find myself to be fashion challenged, as well as style deprived. Luckily when I have extra cash I will invite a lady friend out (often on a pointed suggestion and an enthusiastic offer to help) to pick out clothing.
Men's clothes are a lot more expensive than women's it seems. Picking up several items for under 20 dollars is out of my experience.
I will say that some women I have met have an infinite capacity to shop. A group of us went to the mall one time and I swear the girls went through every store once first browsing, then a second pass trying things on, and then a final visit to actually buy.
It took an entire day! To pick up a handful of items! I was exhausted and had a smile pasted to my face by the second hour.
I can visit several stores, get fitted for a suit, and buy several outfits as well as shoes, and have lunch in about an hour.
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