Splint Style?

I've been thinking a lot about my upcoming trip to New York and what the heck I can comfortably (term used loosely) wear to a grad school graduation without looking inappropriately casual. I'd had a dress picked out for months, and I was debating whether to wear it with heels or flats (or perhaps I'd walk there in flats and change into heels once I got there so that I'd look like a legit NYC commuter). Now that I have The Splint, both of those options are out. It wouldn't fit in flats, and I can't wear heels because my ankle literally will not bend that way. I'm not about to wear sneakers with a dress, but I couldn't justify wearing pants either. Then I got to thinking...what about TOMS?! They're kind of like a hybrid between flats and sneakers, and they're a great cause!

Ashlynn by courtallisonh featuring long earrings

{via Polyvore}

I love the style of those shoes, but I wasn't sure if they were wide enough for The Splint. Then, I found this creation that included a more traditional TOMS design:

wednesday morning brunch by chloeporelmar featuring marc by marc jacobs jewelry

{via Polyvore}

I could even take it up another level and get some fancy TOMS!

{via Nordstrom}

What do you think? Can I pull it off? Any other suggestions for fashion that's comfortable without being too casual?