So lets talk mens dress clothes, because I think they should help you look more "manly". The cut and fit on properly tailored mens dress clothes are designed to broaden the shoulder and slim the waist. This makes your upper body into more of a downward pointing triangle and extenuates your body's natural shape. The best advice that I can give you to look more "manly" is to get properly tailored dress clothes.
Now lets talk about the clothes that Booker is wearing. I like to use this picture as a reference.
The shirt he is wearing is a white-collared dress shirt in either black or DARK charcoal grey. It looks a bit navy, but I think thats an illusion. However, if you wanted to, I would go with a VERY DARK navy. Here is a shirt I found on Amazon
that would work. Notice how it has a white collar, and also white lining where it is rolled up at the elbows. If you want to accentuate your shoulders, I would make some shoulder pads and wear them under your shirt.
Now let's look at the vest/wasitcoat. It appears to be a dark charcoal color, and maybe even a herringbone texture.
It has a rather wide, silk notch lapel. You will probably have to make the vest yourself, I have not found anything close online yet. It is almost double breasted, but the 8 brass buttons are still only one one side. By wearing a black shirt you can get a good contrast with the dark charcoal vest.
Don't forget to get a leather dress belt as well. The one in the picture almost looks dark brown, but I'm against wearing brown with black so I'll be wearing a black belt. Also get a white ACE bandage, or some white cloth to wrap around your right hand.
Looking good so far!