Also, building off the tailored idea, and perhaps more importantly...start by buying stuff that actually fits, or is close to fitting properly from the get go and it'll look infinitely better. People often buy stuff way too big or way too small. I am 6'1 and about 210 lbs. I wear a size Large. I see guys who weigh 30 lbs less, and are 4 inches shorter than me wearing XLs all the time. People don't know their actual size.
Why does Sartorialist have such a hard on for blazers that are too small?
Don't get me wrong, I like clothes that fit closely and really well -- high armholes and very little wiggle room.
But come on, that factory-worker guy above could never button that jacket in a million years. Even if he could it would barely cover his belt buckle.
My verdict: Jacket's too small, rise is too long.
I dont find being different equates to stylish. Some of the thing in that blog look very nice especially the fit, while others look down right foolish. I work near VCU and see some down right funny things on the street. The biggest piece to style that IMO guys get wrong is fit. I work with a lot of guys that have really nice clothes, especially suits, but the fit is wayyy off. I myself am learning this. Just because these guys buy some wacky outfit from the hip thrift store in the large city doesnt make them stylish. I do however applaud their boldness to put it on and rock it on the street.
The best advice I ever got was from a guy that had a small store locally. He said take two guys in the exact same off the rack blue suit. Which one will look more stylish? The guy that takes the off the rack suit and gets it tailored and puts on better/cool accessories will always look more stylish and still be able to go to work without everyone in the office wondering who hired the clown.
If you changed from a t-shirt to a polo shirt it would look ehhh. If you go with a full button down you are formalizing it.
I thought about a different color solid color shirt or something with horizontal stripes.
The guy went with something clean and not Bozo the clown and looks good IMO.