I always go for what seems like the typical Canadian choice, jeans and a hoodie. That way, you blend into crowds if you need to escape, you have warm gear and adequate protection against minor danger.

I basically wear the hoodie and pants costume, but usually "rider" gloves as well (fingerless gloves made of leather). Because, like that other person said, it's not fun to screw up your hands climbing things or going through windows. If it's cold I also wear those thin little gloves, that are kinda stretchy. I've decided wearing a suit jacket isn't terribly inconspicuous. So I'm going to stop doing that.

Posted by lil-trouble Orange, really bright orange. No one seems to notice or care.

For some reason, this has worked for me many times. especially if you have on a reflective vest, work clothes, construction hard hat (if needed) and steel toe boots. I have even signed into sites with this, (Joe Smithson works best)
Places entered this way include Canadas Wonderland after hours, Hydro One sites, Major construction project at a hospital, and at a gov't building.

Oh, and theres also one more thing, your trusty (open anything) tool box in hand, with an assortment of special tools inside.

if i'm going exploring in a large active building downtown, i usually find it useful to wear a dress shirt and tie to kind of blend in with the business types.

For topside urban exploration I wear stuff that makes me look harmless and nerdy. A camera helps with that. For draining I wear stuff that doesn't rip. We've had concerned citizens call the cops just because they saw a bunch of people wearing camouflage hanging about in a local park.

Posted by floss We've had concerned citizens call the cops just because they saw a bunch of people wearing camouflage hanging about in a local park.

Ah, the concerned citizen. I can't stand them, they have no tolerance for those who don't fit in.

I think I dress pretty casual, I like to be comfortable.
Plus I have kobudera on my side.

I usually go with black BDUs or EMS pants with a uniform shirt or a T-shirt that says something like "EMT" or "Rescue". I try to look semi-official to

a) Avoid trouble with the occasional street person

and

b) Convince security or law enforcement that I'm a "good guy" who may have a professional interest (and/or experience) with confined spaces or urban S&R or whatever

Granted, option B is harder to pull off at 2am, but usually the cops will cut you slack if you're not doing anything too retarded. Also, it helps to actually have an EMT, Fire Fighter, or SARTECH background to pull this off.

One thing I've considered (but haven't actually done) is to wear one of my old security officer uniforms and pretend to be patrolling a place. Obviously this wouldn't work if the bona fide rent-a-cops show up, but it may be worth a try.

I usually try and wear somewhat casual clothes so if I'm got it's not obvious that I had plans of infiltrating. I usually keep them dark and I make sure I can trust them for a quick escape of leaping over things and stuff.

I wear layers I can remove so when I make a dash for it I can hide take off my outer layer and blend with the crowd. with a a hope that any distinctive clothing has been removed.