Besides the fact that the Bingham thread was a terrible attempt at showing off style and wealth, I'll play in this one.

But before that, one question: In the Bingham thread you indicate you wear a suit and loafers. But you wear these without socks because you're not yet an older man? That would kill the style.

The simple answer is that you have to wear nice socks with the loafers. Mercerized Cotton thread (fil d'Ecosse aka. lisle thread) will do very well. I even like to wear somewhat funky colors like orange or pink with an otherwise classical outfit.

The only problem I see about loafers in the winter is that they may not offer enough foot coverage to keep your feet warm. So if you have to walk more than a couple of blocks and it's freezing (or below) outside, loafers are probably not a good idea. The other thing is that loafers usually have a leather sole. When it's raining outside that only goes so far. And when they put gravel and salt out to prevent you from slipping that's about the worst thing you can do to fine shoes.

The shoe I mostly use for traveling is the Cole Haan Air Jackson Two-Gore slip-on. It's a slip-on shoe that is much more covering than a loafer but just as comfortable made of fine veal nappa and with Nike Air Technology in the heel. The sole looks like leather but is rubber. So it is also good to walk in wet weather. The design is very modern and simple with a slightly square toe and minimal stitching with makes it a bit more elegant. Exists in black and brown. It will also stick to your feet better than a normal loafer which provides an extra measure of safety.

I wouldn't really wear sneakers with a suit if you are over 30. It looks too much like a fashion victim. Only exception I'd make are some high fashion sneakers like Prada, Hermes or Tod's make them in full leather. I have an old pair of Prada slip-ons that I have worn with a suit. They are pretty run down now so I don't do that anymore but they were awesome travel shoes. Looked a bit edgy with a suit but it was OK because of the futuristic styling. And they were very comfortable and quite water resistant so my feet would stay dry even if I got caught in a downpour.

I definitely hardly ever wear anything that requires laces anymore when I have to go through security. But I usually have a second pair of lace up shoes which might be sneakers. Even sneakers are not highly crushable in your luggage and the more voluminous form will erode the advantage you get from being able to crush them more than a normal shoe. They will still be lighter in most cases, though, than a Goodyear welted leather shoe.

Till