#3: Get an outfit
If you need to say Valentine's Day is the reason for buying an entire outfit, by all means, go out within the next couple of days and pick something out. I recommend you buy some fun black, sheer hosiery with a good design. Sheer black hosiery is very flattering and slimming to the legs. Buy a few pair if you want, but I think it's a good place to start.
Now, don't mind the heels in the drawing. I love a beautiful pair of heels, but truthfully, I'm unlikely to wear them more than three times a year. You need to figure out what kind of shoes you can get that are cute and stylish but also comfortable. I solved this problem a year or so ago with a pari of No. 6 clogs. I shudder to think that one day soon they may go out of style. It's like you're wearing heels but you're secretly not. They're that comfortable. But maybe your thing is a nice pair of oxfords or a nice pair of booties or flat riding boots. Who am I to say? Just get a nice pair that fill all your criteria.
I know it's cold out, but if you're shopping specifically for your dateless valentine's day, just go ahead and buy a pretty dress. Dresses always make me feel nicer than pants. Plus, when you get the right kind of dress, it's much less uncomfortable when you overeat. And let's face it, as a spinster on this holiday, you're bound to overeat. So get something that's fitted to the waist but loose the rest of the way down. Believe me. I know what I'm talking about here. We all know I like to eat.
So there's your three-piece outfit, but You can also add a sweater and a scarf. And of course you'll want to wear some tasteful-yet-sparkly jewelry. Just make sure you get something you can wear over and over. If it makes you feel like you look good, and you can stuff yourself without wardrobe-related discomfort, I'd say you've got a diminishing cost-per-wear situation that can't be beat!