When you can only pack one pair of shoes

black ankle boots. I like them from suit to shorts.

Unless it were absolutely imperative to travel unemcumbered by luggage, I couldn't imagine not having at the very least two pairs of shoes: one dress, one casual.

Simple black monk straps.

Same as Agent5. Three eyelet black ankle boots, with a stacked leather sole and round or chisel toe. I try to travel as lightly as possible (I try to limit myself to a messenger bag and an overnighter for everything); but for the most part, I'll wear sneakers (Converse Chucks, which take up practically no space) and carry one pair of proper leather shoes - absolutely no shoe trees. I'll bundle socks and stick them into the shoes for structural support.

No particular reason. I just think black is easier to match other colors than brown. Also my overcoat is black leather.

I choose black cap toes laceups because of the two goals of the trip (business and pleasure), the business is more important.   I haven't quite made up my mind on the black shoe brown shoe issue yet, but the question for me is, "Would I rather be tisk-tisked by the executive I do business with on Thursday morning because I am wearing cordovan/antiqued brown shoes with my navy suit,"  or "Would I rather be tisk-tisked by the museum guard on Saturday afternoon for wearing black cap toes with my chinos?" When I choose just one pair of shoes to take on a short business trip, I'd rather have people say that my shoes were not right for pleasure than say my shoes were not right for business. Bic

I've never heard of this.  Is everybody else aware of this and I just missed the boat?  If so, what is the story/rule behind it? Kevin

My vote for a single pair is Norwegian-front (split-toe) bluchers/derbys. They are "good enough" for most business situations and will also work casually while something more businesslike such as cap-toes would not. As much as I generally prefer the richness of brown, in this case I'd choose black to better cover you at night. There are casual pants other than jeans or khakis. Grey slacks would cover you in the evening and work better with the black shoes. If you are going Down Under, a pair of RM Williams boots would do the trick and so would cowboy boots in Texas. Or go with what GQ has been touting recently and wear sneakers with your suit. With so many casual shoes being plain-toe bluchers these days, I wonder if their standing as being more formal than nearly all other designs is no longer true. I'm thinking that some nice black plain-toe bluchers could work casually as well as for business. -Ed

My advice: Go with black; so much more versatile than brown. Brown is great, but if you are only going to take one pair, make it black. Either go with a standard lace-up, or, my favorite, a monk strap. You'll be able to wear this with suits and dress apparel, as well as casual wear. As Bic stated, there might be a problem with black shoes and khakis. Problem solved - choose gray flat-front pants or higher-end dark jeans for casual days. You'll be golden if you opt for the pair of black shoes. Nothing will be more versatile for you.

Having to make twice yearly trips to Europe, I find it more important to pack an additional pair of shoes than too many clothes. I never check luggage either, so I start with black trousers and build around that. Black plain toe shoes are the most versatile, I find. One leather sole, one rubber. Dunkleman makes a great travel tree - maple but carved out into a shell - very light. If you are traveling and get caught in bad weather, and you only have one pair of shoes, the next day is miserable.

Funny...I feel just the opposite. Brown is, for me, far more versatile and elegant, but it must be the raging Italophile in me speaking.

I have a pair of plain toe Blucher oxfords cordovan color. Shell Cordovan leather. Goes nicely with blue or grey. Can be worn with suits or casual clothes.