Visiting vacay noob on an adventure

[charlitazing]

You can skip to last paragraph where I will ask for help regarding a messenger bag if you'd like to skip my journey.

So, I am on vacation in the US (since late December) until mid-March and I have decided to update my wardrobe as the clothes in my country are poor or overpriced mall brands. One thing I do buy for cheap are Pima cotton undershirts and boxers. Most people, including me until I started lurking on here, think PRL and Tommy Hilfiger are the pinnacle. The prices make it seem that way.

What have I done so far? I have been shopping at thrift stores using the thrift thread as a guide and I have done well. I started with one black dress shoe (relegating to casual use), one casual brown shoe, three blazers (two tan and one blue and green), two ties, two dress pants, lots of CK, Tommy Hilfiger, RL dress shirts that I'm still really happy with and will continue to wear. I don't have a suit, because I gave mine away after losing weight. I'm a university student and I'm easily the best dressed guy as I'm the only one that wears polos and dress shirts and somewhat dressy shoes, but I want to step it up a bit. Of course, I'm not expecting Turnbull & Asser, Kiton, Oxxford, GG or even Carmina, but I drew up a wishlist of what I wanted to take back, as follows.

1 navy suit (check, thrifted DB BBGF suit)
1 navy blazer (check x2 , thrifted Joseph Abboud and a Tom James Executive with H&S cloth)
1 brown blazer with windowpane pattern (not yet, but I may end up crossing this one out)
1 thin coat or jacket (check, thrifted no brand jacket)
1 pair casual suede shoe (check, 85% discounted new Cole Haan shoes)
1 pair casual brown shoe (check, 60% discounted new Cole Haan wingtip brogues)
1 formal black shoe (not yet, struck out at thrift stores but am looking at AE Park Ave on eBay)
1 pair corduroys (check, thrifted BB corduroys)
1 pair dress pants (check, only one I kind of regret as they are Perry Ellis polyester but they'll do)
X dress shirts (so far eight, mostly cotton but two are linen, Tyrwhitt, EZ, Etro, etc.)
X ties (so far four, light blue, burgundy, green/grey, brown Etro, BB, Armani, EZ and I regret passing on a Carmel paisley pink tie)
2 pocket squares (haven't come across a single one at the thrift stores)
1 messenger bag (not yet, will ask for help shortly)
1 pair of Italian boots (buongiorno boys)
1 Swedish-made penis enlarger pump (I'm telling you, baby, that's not mine)

Thanks to this site, I also picked up some shoe trees! I'm not exactly a hard size(38/39S, 6 drop), but the 38S, small and 15/33 sections are really small compared to the rest of the sizes. Regardless, I am very satisfied at the $210 I've spent on clothes that are very near new (that amount would buy three Tommy polos at home). It's so weird passing on Brioni or Burberry albeit because they're a bit worn, but I love this little hobby.

So, my biggest expense will undoubtedly be the messenger bag. I need it to fit a 13" laptop, a notebook, and an anatomy textbook. I am pretty decided on leather and I need some guidance. No luck at thrift stores and I've resigned myself to eBay as Saddleback, Filson and Koch are too expensive for my budget of $200 at the very max and preferably below $150. I really like Floto on sale and they are the reason I expanded my budget by $50, but I also looked at Patagonia's well-priced Black Hole messenger bag as an alternative to leather. I am not at all excited at canvas. Any experiences, alerts, or further recommendations are highly welcome.