Hi Brandon. First of all, I don't feel that I'm expert enough to critique the suit, but mensimageconsultant seems right on. For a guy your size, it might be helpful to look at some other heavy guys who are well dressed. I used to weigh in at 280 so I have had my own challenges trying to find things to wear that presented me the best. I've pulled a couple of pictures of guys who are heavier but who look great in suits. At any rate, take a look at these and apply them to your re-make. Look at the Horatio Sanz photo from GQ. His suit covers the butt and doesn't pull across the chest. Note that even though it is a modern cut suit, the legs are wide enough to cover his girth in a way that makes him look slimmer. My guess is, these photos make you actually look heavier than you are because of the options you've chosen. In others, you can see that the belt area doesn't have a body crease the way yours does in the photo. you might be better off adopting a larger waist and adding suspenders. So from this, I'd say 2 button stance, suit that covers the rear, pants that are wide enough to drape really well, and since he has a cuff, they are probably pleated, which some suggest for those of us with larger waists. Also, note that the sleeves on his suit are longer than yours and the shirt sleeve shows about an inch. Now in the Following photo, we have Cedric the Entertainer, a bigger guy who always looks great. This is a casual look, jeans, open collared shirt with a jacket. Note that the jacket is 3 button, same as yours, but it is longer (just below the crotch of the jeans). The button stance is lower (note that the lowest button is at his belt, and only the middle is buttoned). In your case, if you added a 4th button to your jacket, it would still be a couple inches above your belt. Also in this photo, you can see that there is a more structured shoulder that adds width that creates more of a taper at the waist. In your photo, the shoulder is the narrowest part, and then the bottom of the suit cuts around your widest part. That is, no waist... also in the two photos above, there isn't a back shot, but I guarantee you the jacket camouflages any love handles they may have. In your suit, because it pulls there, your love handles are accentuated. One more of Cedric, and I'm not sure you want the white shoes. Again, this is a very stylish man who obviously loves looking good. Now in this case, I'm not sure you want your pants that long (hector's seem great), but again, note his jacket comes below the end of his zipper by at least 1-2 inches. More width at the shoulder, tapered to the waist. Also check out the lapels. it buttons easily with no visible pulls. Note his lowest button is at the belt line. I take from these pictures that great looking heavier guys, should wear the jacket longer than indochino suggests. This is one of those questions of Fashion vs Style. Cover the butt, or have someone measure you from the bottom of the collar to the floor, and then make your jacket half that distance for the right proportion. I would consider a more padded shoulder and bring the lapels wider. Some have suggested that you take the distance from your shoulder seam to the lapel and that a lapel should be about 40% of of that distance. So all of these photos seem to have a lapel in the 3 to 3 1/2" range. Where you can define the line from the photos, they all come to just under half the width. More fabric in the chest and waist would also make the jacket drape better. Lower the button stance so that the bottom button is at your belt. As to the pants, I would go to a store an try pants till I got to the size that would button without creating a muffin top, which you've created with the ones you're wearing. Then I would add pleats and wear suspenders. I would also widen the leg of your pants somewhat to drape in a straight line from top to bottom, without any pulls behind the knee or the thigh. That will mean adding an inch or two or four to your thigh and knee measurement. I hope this isn't offensive to you, but you're a nice looking young man and the suit, as is, makes you look dumpy, rumpled etc, when what I think you were after is the look of the Horatio Sanz photo.