I would stick with the less is more philosophy - buy less shirts at a higher price point. Quality > quantity.
I snapped-up five NWT Nordstrom Egyptian cotton dress shirts this week from Goodwill for $25. Would not totally discount the cheap route just yet... Say, zippo, speaking of Nordstrom's and plaid/stripe-y button-downs, it looks like you can cop a few here for $48 on sale: http://shop.nordstrom.com/c/john-w-n...om/mens-shirts
Anyone interested in designing some streetwear watches for $5 just to submit your design and have other users in the community to vote on them? I created oardx.com because I want original clothing. winner will win $250
Let me know if you're interested to design some cool streetwear watches to begin.