True story: a few years ago, we went to Key West with family for a wedding. It was a blast, Ross and I spent entire days exploring the island and seeing Hemingway’s gorgeous old house (and cats!) and I’ve pined for it ever since. The whole time we were there, though, I relied entirely on my collection of wedges and heeled sandals. Because, really, I had these outfits planned and I didn’t feel like I had any flat sandals to do them justice. It didn’t slow me down most of the time, but I had blisters to show for it and man did it make all those wooden stairs at the hotel tough. I bring flats on vacation now (this probably has something to do with a “long walk” no longer meaning a mile or two since moving to Chicago… now it would have to be four plus miles to qualify, and try doing THAT in heels) but I’m still not the world’s most practical person.

Example: I have some fun shoots coming up that require dresses a tad bit longer than what I usually wear, since I often end up on the ground or in some sort of awkward position when shooting. Anyone else would have settled for some kind of practical, long black dress that could be worn in pretty much any situation. I, in turn, scoured all my best sale sites (hint – sometimes the department stores actually have better sales than Outnet and the like) until a bright blue DVF dress went on crazy clearance, and scooped it up. Because why settle for anything remotely practical when you can go all out?

The flip side of this is if I can’t Do Something Right, I won’t spend money on it. This infuriates Ross to no end, because it means that I end up clinging onto things way past their prime. He’s gone through at least two generations of iPhones and – no matter how many times I borrow his while we’re out, or curse myself for not having a smartphone when I’m waiting to meet clients – I still have a cherry red LG Shine from 2007. I just keep telling myself that when it breaks I’ll find something new, but for now data plans are priced so absurdly it’s not worth it. (See also: my complete lack of desire for any sort of TV, and the ferocity with which we cling to our hand-me-down 2002 first gen Prius.)

So it’s all of this that’s foiled any purchase plans I have for luggage. On one hand, it gets really dirty and banged up in the course of traveling, and it’s hard to think about investing in something that may very well be lost (O’Hare has some of the worst rates for losing luggage. I’ve flown out of ORD my entire life, and have yet to experience that, but it terrifies me every time I fly. Almost as much as the actual flying terrifies me) or beaten up. Plus, we take full advantage of how cheap it is to hop the brown/purple/red line to the blue line, which means that our suitcases a) need to roll and b) WILL be rolled through the who-knows-what-that-is game show of the subway floor.

As much as I’d love a cute little number like one of these:

(source)

they just won’t work for practicality’s sake. Are you a fellow plain black roller suitcase traveler? Have you found a fashionable-yet-reasonable alternative?