I held off on raving about this place until after I moved out of town because I simply didn't want more competition for appointments! The secret has been out for awhile now that this place is legit.
I went to Crow's Nest for the better part of two years while going to business school in Toronto. Appearance is scrutinized at b school, so it was important for me to get a good haircut and Crow's Nest never disappointed. It's a cool place with a bunch of characters that all take their craft seriously. The ambiance is prototypical "hipster barber shop" but it doesn't feel forced or pretentious at all. Comfortable chairs, good music and always amusing banter. Furthermore, having lived in several cities and gone to similar establishments, the price is VERY reasonable.
I went to a few different barbers here before settling-in as a regular with Tristan. Everyone has different preferences, but for me he was simply the best barber I've ever been to. He is surgical with his attention to detail and takes his time getting your hair exactly right. If you're like me you find it somewhat hard to describe what you're looking for, but he listens intently, presents different options, and makes suggestions that always work out.
I've seen other yelp users complaining about difficulty walking-in. I recommend booking about 8-10 days in advance. It's not a big deal because their online booking system is very professional and convenient. Yeah, if you try to walk-in you may not get an appointment, but then again the world does not stop and start at your convenience. Why not just make an appointment like an adult...or go to Supercuts?
Love this place and will probably go out of my way to wait for a haircut here whenever I'm back in Toronto.