I have a horrible confession to make. I wore the same jacket two days in a row (but for my weekend job, teaching, so nobody saw me repeat). The PS was a gift, but I like the way it looks with the jacket.
I'm afraid the fit of your jacket and trousers isn't quite up to snuff. Your left jacket shoulder noticeably overhangs your shoulder, resulting in a big ol' divot. The jacket is also pulling at the waist, too short in the body, and much too short in the sleeve. The relationship between your shirt sleeve and your jacket sleeve is correct, because the shirt sleeves are also too short.
The jacket length being too short means that the button stance ends up rather high up on your torso, and this combines with the too-low rise on your pants to leave a gigantic triangle of tie and belt -- which you really don't want. They're also a little long. The fit through the legs isn't too bad at all. I like your shirt collar, though your tie looks a little satin-y, and I'm not sure what your pocketsquare is doing -- not quite what it should be. Is the shirt white or off-white? Off-white is okay, though you might want to consider light blue.
That said, I'd say as of right now your taste in combinations is being let down by your wardrobe -- although there is room to improve there, the fit issues are taking things down a few notches.
I think that is great advice! The shirt is actually grey with white French cuffs. I am trying to focus on building good pattern combinations before I get everything tailored because I am currently losing some weight. I can certainly see some areas where I need to improve. I think I might be able to fix the divots by removing the ample amount of shoulder padding. Thanks for the awesome input.
Warning: Spoiler! (Click to show)
This is a beautiful combination. The tie is a lovely shade of burgundy, especially against the white/grey background.
Unusually smart for a weekend, but I did a little work this pm, so...
StyledbyShawn, your jacket is much too tight and short - you should try sizing up. You might think the shoulders are wide, but they aren't - the divots are there due to strain at the armholes, which means they are far from sitting correctly. That's probably due to chest being too tight, and also because your shoulders seem to slope and pitch forward more than the jacket's. Sizing up sometimes alleviates these problems, and helps making the jacket look smoother. You should also try to find something with less waist suppression.
Positive: I really like the colours / patterns of your outfit :)
Hmmm: Pocket square colour/shape It could be dark reds, maroons, and browns patterned silk puff.
negative: Jacket is much too short and too tight, Shirt sleeves are too short, trousers have a very low rise.
StyledbyShawn: Even if you fixed the shoulders (which... maybe. Sometimes you get a divot from an issue with shoulder padding, sometimes it's due to the shape and width of the shoulders) the jacket would still not fit well enough to be worthwhile
Moo: That's kinda cool. The sweater reminds me of Tom Hardy in Lawless. I can't really get behind the untucked shirt on purpose -- my inclination is to tuck my shirt in and then untuck it as my life requires it. Maybe if the tails were shorter than the sweater, and the pants weren't well-pressed wool -- chinos would make sense. This looks like what you change into when you get home, not a fully-fledged outfit. Maybe you were going for that, but I just don't get it. I'd be uncomfortable going out in it.