As far as sub-$300 shoes that look pleasing, check out Meermin. I find they look very similar to more expensive brands, probably because they are owned by Carmina.
Well if you want to try it on in person your only bet is probably J Crew, Banana Republic or Hugo Boss. I'd say Suit Supply is better than all three though in construction and cost. Their slimmest fit is the Washington.
The answer is getting the navy London two button suit from Suit Supply for $499. It's cut slim but with a conservative color and lapel so it doesn't look "fashiony" but fits well. At your height and weight it should fit you off the rack with perhaps minor alterations.
I was planning on buying the 3 piece Blue Lazio linen suit for a wedding in LA mid October but they stopped selling it apparently. Would wool suits be okay for LA in October or do I have to stick to a linen or linen blend? Any thoughts appreciated.
1. Move your hair part up a tiny bit
2. Put small/medium amount of American Crew Fiber all over your hair
3. Instead of styling your hair completely across your head to the right, style it forward but a slightly to your right
4. Push the front up a bit and use your fingers to mess the top up to look more casual
5. Use hair spray to finish if the messy part doesn't stay up