Agreed. Or some Vans slip-ons.
no.
I would go with something simple in terms of shoes. A good pair of
leather Jack Purcells or
Adidas Sambas or
Adidas Stan Smiths can't go wrong. You also can't go wrong with a pair of white/black/navy Converse all stars.
For the jeans, try a darker, more fitted pair - at least tighter around the ankle and shines. I don't mean go all hipster and start wearing girls jeans, but something less baggy and more fitted will definitely look better and more modern. I used to wear baggy jeans, and the switch to fitted felt weird, but a) it looked better b) made me look slimmer c) gave a more modern look. You don't have to go out and buy a pair of APC's or Nudie jeans. The Gap has some that will be perfect!
I'm not really a polo person, but if I was going to wear a polo, I would pick one more along the lines of what you wore in the first picture (maybe a smaller stripe and maybe something in the blue/white/grey/black area). If you like solid colors, try something a little lighter, like a light blue, or a light green.
I'm not really a casually dressed person. I like fashion and designer stuff (Paul Smith, Etro, Club Monaco, Moschino, Ralph Lauren ect), so I'm more a
shirt and tie/bowtie with a sweater or cardigan, or a hoodie type of person, but I've included me in the only polo I own (rarely wear it), just to give you an idea of what I mean.
Sorry about the filthy mirror.
Shoes: Adidas Stan Smiths
Polo: Club Monaco
Jeans: The Gap - Skinny Fit
Anyway, you're headed in the right direction! I hope my tips are useful and good luck with your future purchases!