I'm Hugo. Been lurking for…quite a while, actually.
Pretty much the only time I don't wear all-black is during Taekwondo…where I wear all white (apart from my belt, which is black). The upside of only wearing black is that there's no colour-matching to worry about. I can't really remember why or when I went to just wearing black…I used to like colours…many years ago…. (Not that I ever put on a suit jacket, due to the unbearably hot weather we get for most of the year, but were I to wear a suit it would be all black as well.)
I like leather on shoes and belts but rarely on jackets (although my camera strap is rawhide so that sort of covers the idea of having leather above the waist).
I used to have one pair of shoes that wasn't for school (for which I had black loafers): Black trainers. I'd wear them with trackpants and a t-shirt or jeans and a t-shirt. Then I got a pair of Dr Martens 1460 boots (which wear with jeans, where I cover more than tuck. I wore these for a week in Huangshan walking up and down stone stairs for 12 hours a day — barely scuffed them and they really gave me no problems at all). Then a pair of Geox mocs (Monet, I think, but suede. Black, obviously) which are still my go-to shoes. Sometime later I got a pair of Toms, which are on the verge of falling apart just a few months later. Then a pair of Timberland boat shoes. Today I bought a pair of Geox Rubbiano ankle boots (which I can find no opinions on) — they're basically Chelsea boots with a zip instead of elastic and a jodhpur-style, not-really-functional strap at the ankle. I chose them because I'd wear these with a suit (conformity plays no part in my choice of clothing), skinny jeans tucked (where the strap makes the boot look less "empty") or fitting jeans covering the strap.
I haven't worn trainers in…a year, really. Taekwondo is done barefoot (or with specially-made shoes that weigh 1/2 to 1/4 that of running shoes but wouldn't last if worn outdoors) and IMO you'd be insane to do headstands with shoes on (I do yoga every day). I never play cricket "seriously" — just on a quiet street with some friends…so I can get away with not wearing trainers (it's not that I actively avoid them — they just call me up at the wrong times and all that. To be fair, they play in slippers.)
I mostly like long coats. I don't have…any…jackets which don't at least cover my pockets. Not that it really matters — with Hong Kong's weather, you take the coats out for about a month and then it's back to as much light (not in colour) linen and cotton as you can get your hands on.
My criteria for choosing shoes basically boils down to one basic criterion:
- No matter what they're designed for (very formal, formal, smart casual, whatever), I have to be willing to wear them as I would any other pair of shoes — walking (as I so often do on a spontaneous decision) for 2 or 3 hours in at least slightly wet, dry and really-hot-and-dry conditions. Which is why I'm not sure I'll ever get leather-soled shoes.
I treat most of my shoes the same if they get wet — wipe off excess water, allow to dry at ambient temperature (or slightly warmer if it's during winter) then polish/treat with cream (if they're leather, which…most of my shoes are…). So nothing delicate — I buy each pair with the assumption that, at some point, they'll get at least quite wet. Surprised my mocs have held up, actually — never expected suede to be quite so tough. Never expected they'd become my most comfortable pair of shoes (probably because I wear them so much).
So now you know about me.