I normally don’t answer Tumblr questions from womens unless I fornicate wittem. But I can make a concession because you are in a pickle. At $80, the Bass Barrett longwing is my number one suggestion—a “starter grown man shoe,” if you will—seeing that it will leave you with a windfall of cash to buy some sexy lingerie for later that evening. Everybody wins.
Other options would be to scout Gilt for a pair of Heutchy or Florsheim longwings, wingtips or oxfords. Both labels are regularly featured on Gilt, and Heutchy usually goes for about $129 while Florsheim can go anywhere between $149 and $349 (for the Duckie Browns).
Oh, and happy anniversary.