I am glad so many of you were willing to window shop for me, and really enjoyed checking out all your suggestions.
Here is the winning ensemble, which was recommended by Brie:
I chose this shirt in a lovely plum color--it's a little dressier than my usual crewneck style, and the color will go with every pair of pants in my closet! The jacket is a fun departure from my usual style. I wouldn't have picked it out on my own, which was part of the point of extending the challenge in the first place. Thanks for the inspiration, Brie! (Due to sales, I got both pieces for $30 total!)
I must also make an honorable mention. Though this shirt was suggested after the contest deadline, I ordered it as well, especially since the commenter shared a free shipping code.* Thanks, MH in OH!
Thank you again for a fun time. I bookmarked a few of the other pieces for future reference and appreciate all the recommendations!
*Before placing my orders, I remembered this advice about searching for free shipping codes. Though I was unsuccessful in finding one for Sears when I needed it, I still think it's a great tip! I also used Ebates so I could earn a little cash back on my purchases.