I will be traveling quite a bit over the next few months, and the less luggage I have to tote around with me, the better. I can get along fine for a few months with only one of the fifteen different off-white sweaters that I own, but the real difficulty is choosing shoes. First of all, because there are so many useful types of shoes that don’t substitute for each other easily, and second, because shoes are real space hogs in a suitcase.
Before setting out, I decided I’d have to make do with only two pairs of shoes.
Which two pairs you choose will depend on the other clothes you’re packing, of course. I’ll be dressing casually most of the time, but will also have plenty of occasions to wear coat and tie.
I ended up choosing one sneaker and one oxford. For both, I think it’s best to choose a dark color. Dark colors stand out less, and are therefore less tiring to people you see day after day. And they also go better with a wider variety of colors, so you don’t get stuck in a situation where you can’t wear your green sweater because the only sneakers you brought are bright red and together they make you look like one of Santa’s elves.
The choice of dress shoe is necessarily a compromise. Ideally, you would want to wear a derby, possibly in suede or scotchgrain, to wear with sport coats, and then an oxford to wear with suits. But if you’re limited to just one pair, I think wearing an oxford (especially if it’s a brown one, like the one I’ve chosen) with a sport coat is lesser sin than wearing a derby (especially if scotchgrain) with a suit. I’ll be wearing both sport coats and suits sometimes, but even the suits need not be investment-bank-formal, so the brown oxford is a good solution for me.
If you were going to be wearing conservative business suits all the time, then you would probably want either an oxblood or a black cap toe instead. If you’re ever going to be in evening wear, then black for sure. A black cap toe is usually listed as the first dress shoe a man needs. It’s not a bad choice and every man who wears suits should have a pair. But for the way I dress, I rarely end up using them. For me, a dark brown is good enough to get me through a few months on the road.