I don't know how much my advice is worth, but i think that you would look a lot better with a more simple colour scheme. Taking you last fit, maybe replace the purple tee shirt with a white one, and the blue jeans with some grey or black washed ones.
On a side note, since you have a wider build than a lot of us lanky boys, try a slimmer profile up top. The bomber is awesome, but, at least to me, makes you look top heavy.
On yet another side note, I had a listen to your music. You Never Told Me is great.
Any constructive advice is gold to me. Thank you for your thoughts.
I really love the bomber--just got it last week--and I'd be thrilled to figure out a way to make it work in my wardrobe. I have a bunch of SLP pieces (two denims, the satin bomber and this one) and they're all cropped rather short. I'm hoping that my height (5'6") will work with them as they'll sit more or less at the belt line. I thought the purple would be a nice contrast against the black and the blue but I can certainly see your point. I have a few pairs of pants at the tailor getting tapered so there will be plenty more to work with in a week.
Thanks for your kind words on my music. Much appreciated. Cheers.