So I was in the same predicament you are in about a year back, and honestly everything everyone has said so far, is really really great advice. Like ksteezy mentioned, check my post on thestyleblogger; just click here
http://www.thestyleblogger.com/1245...ps-for-heavier-guys-featuring-sergio-arteaga/. and look at the looks I'm wearing. Yes that is me and that is all my own clothing.
Like many have stated, it is all about fit. Just looking at the pictures you posted, I am assuming your shirts are about 1-2 sizes too big. Notice that in none of the looks I have on, the shirts are overly loose but neither are overly tight. Your shirts just be roomy enough to move but nothing too small that you feel you're going to pop a seam. Your pants are way too big for you. Get your pants hemmed and tapered as it was already suggested. It's not about trying to make yourself look smaller, it's about making yourself look the size you are. Not to mention my feature, but notice my dress pants tend to not be overly roomy in the leg and don't have puddling of fabric because of them being too long.
If you're on a budget checkout my blog as well. Honestly, depending on your neck size, you may be able to find pretty nice shirts at places like Marshall's, TJ Maxx or Ross (if you have one nearby), for $10-15. I'd even say try Target's Medona dress shirts, I personally have 2 of their shirts and I really like them, granted I had to get them taken in due to dropping some weight. Your undershirts, go v-neck when not wearing a tie, not going to lie I wear crewnecks here and there but usually it's when I'm wearing a tie since the shirt wont show.
First keep it simple, start by not wearing any squared toe dress shoes, lace up or loafer. Squared toe dress shoes only make your feet look wider and therefore only adding width to your frame. You don't have to spend an arm and a leg either for some nice simple dress shoes. My suggestion is next time you go to JCPenney to check
these out, they also come in black I believe. For $60 each it's a great investment and will make your outfits look even better. You want a shoe that matches the natural shape of your foot, not one that makes them look square.
I hope this helps and please don't hesitate to ask more questions or PM any of us.
Thanks for the shout-out ksteezy!
I'm on-board with the $50-75 idea and the list. I already have in mind what I'll probably end up getting for some people; based on who will likely participate.