Reddit mentions of G.H. Bass & Co. Men's Buckingham Classic Buc,Taupe,12 M US

Kudos to him for wanting to improve his personal style and for you in helping him to do so! Here's my take:

• The polo/khaki chinos look has pretty much been bastardized by the workforce as some sort of semi-acceptable business-casual getup, hence the dorky vibe that you get from it (stripy patterns really don't help either). That said, it's doable with an outerwear layer (#16, #17, #38 look much better than their jacketless counterparts). And for the love of god, never, ever tuck a polo.
  
  
• The sweater vest is incredibly hard to work into outfits given that the embroidery smashes it fully into casual territory, yet it's a sweater vest. I'd also be careful about pairing ties needlessly into outfits (especially with not-dark-wash jeans) and reserve it for actual formal events. Outerwear + collared shirt or just a shirt worn in a casual manner should be more than enough to give off an age-appropriate vibe.
  
  
• Outfit #25 looks fine as a fairly minimal casual outfit. I guess the jeans could be either a darker wash or a super light wash, but it really just depends on how well both pieces fit along with his shoe game. Speaking of which, he really needs some sort of minimal white sneaker. If you've the funds to spare, ASOS has a lot ranging from $15-30 with free shipping at $25 or above and a 25% discount if either of you are students.
  
  
• On #27, the light blue is fine. If it was any darker, he would look too blue. Also, you should check and ensure that the fabric on that shirt is a casual one (feels rougher and thicker). If it's a thin/smooth/glossy fabric, it might actually be a dress shirt, hence why it would seem off when you pair it with casual stuff. Tie is indeed too much in #32.
  
  Miscellaneous:
  
  
• No such thing as too much khaki. There's a ridiculous level of diversity in that color, ranging from shades that verge on olive to ivory/ecru, and all of it is incredibly versatile.
  
  
• His shoe game will also be incredibly important and will be the one thing that ties everything together. My favorite beginner versatile shoes are Bass Pasadena/Buckingham or something along the lines of their style (suede bluchers). Their texture allows for casual wear and the design works all the way up to business-casual levels of dress. Minimal sneakers and then some sort of brown lace-up will help tie everything together nicely.
  
  
• As a fellow poor person, I strongly recommend that you guys look into learning how to sew/tailor your own clothes. Simply learning how to dart and hem shirts will allow you to get the best fit out of cheap buys (similar to a lot of my wardrobe). Knowing how to hem pants can also save you a lot of headaches during the shopping process.

Sadly I know nothing about Canada but I assume Amazon ships there? These Taupe Bucs are ones I picked up recently and I love them to death. They're a summery casual shoe that also looks great with chinos (not sure as far as a suite).

My standard size is a 12D and that for me fit perfectly. Getting a slightly darker shade of brown would lean more toward formal over summery so choose something to fit the bill.

As one last note: the "dual leather" suede/leather (technically suede is a kind of leather but that's beside the point) shoes you linked will generally be looked down upon by MFA. I don't mind them as much but they are a bit out there.

Whatever floats your boat. Just trying to give my 2 cents.