Now this is a good thread!
Well right now I'm wearing a black waistcoat and black jeans with pocket watch and green Henley shirt. But usually I wear bootcut jeans with a Henley shirt and a double breasted cardigan. I also often wear a biker leather jacket.
First of all lets rule out the ones I wouldn't wear. Some aspects of the first doctor's are okay but wouldn't really suit anyone so he's out, the second doctor is most certainly out, the third doctor is also probably out because I couldn't pull off velvet and I doubt I'd wear a ruffled shirt (maybe one day though). I wouldn't wear the fourth doctor's either as I dislike scarfs and floppy hats, plus he look too tatty. I do like some elements of his JNT wardrobe mind you. His waist coat is pretty nice and I prefer the more harmonious colour scheme. When I was a kid I wanted a fifth doctor jumper like he wore but now I wouldn't and I think I can safely rule out his outfit too. Now the sixth doctor's a tricky case for me actually. I don't like all the colours but I love the basic template of his outfit. Maybe if it was black with red lining and all gothic looking I'd go for it but I'll be safe and give it a no. I wouldn't wear the seventh doctor's outfit either as once again a hat is prominent (funny enough though when I was a kid I had a straw hat and actually dressed somewhat similar to him, my favourite outfit was a red shirt, an old fashioned waistcoat with a lovely pattern on it and a green blazer). But now I wouldn't really want to base my wardrobe much on his attire, so I'll give him a no. However I do like his 1996 outfit minus the hat and crazy hairdo so that can sit in the maybe pile. The eighth doctor though, hmm. I like many elements of his original outfit, wouldn't stick out too much in a steampunk convention. But the coat is kinda velvety. And I couldn't see myself wear it day to day. Hmm. That's another maybe. His leather outfit is a different story though, I've actually been searching for an affordable jacket just like that (but probably in black) and I do wear jeans a lot. I really like his look in this outfit. Yeah, I'd wear this. I don't think I'd wear his TNOTD outfit though.
The War doctor, hmm. I don't really base myself on his look but I could see myself looking like that one day, the beard, the waistcoat and the leather jacket. Sounds like me (except for the beard but one day I might grow one). The ninth doctor would probably have to be another ryes due to the T shirt and the leather jacket. Tenth doctor though, hmm. He's my default doctor, his outfit comes into mind when I think of Doctor's clothes. But would I wear it? I really do like his outfit. Maybe, just maybe. Now the eleventh doctor, I think one day I could see myself rocking a tweed jacket, and someone once said my hair reminds him of his. His second outfit especially appeals to me, in fact apart from the bow tie I could see myself wearing all of his second outfit plus purple is my favourite colour right now. The twelfth doctor's outfit is also very nice, I like his buttoned up shirt (top-button swag!) and his nice Crombie, I could see myself wearing the latter one day.
So I guess my conclusion would have the Eighth Doctor's leather outfit and the Eleventh Doctor's second outfit being the winners here. At least they're the one's I'd like to look like most. But the one's I probably look like most right now is probably Nine's but with a waistcoat or double breasted cardigan. I used to base my hair of Tennant's when I was younger and he was the doctor but that became rather stale. Now out of all the doctor mine's probably most like Elevens. But I have shaven sides.
