Dandies must maintain their unique sense of style and know when to break the rules, when to bend them, and when to create new rules altogether. Other times an idea from thriftiness, poverty, necessity, or accident spurs some creativity. Canvas shoes and suits is one of them.
In East Africa, canvas shoes are a staple of anyone who can afford to purchase more than a few pairs of shoes. Why; they are cheap, resole-able with some African ingenuity, easily dyed, customizable, de rigeur for school children, and easy to clean. Another one of my father's stories comes to mind, when I was growing up he always was trying to find canvas shoes and buy them for us. He finally gave up on getting them and realized American school children wear sneakers and one pair of dress shoes to school. Well, after one of his relapses I decided to ask him why he was obsessed with them.
He replied, "I remember wearing them to school. We were supposed to wear dress shoes but the British under funded education and we were too many for my father to afford proper shoes. Instead he bought us canvas shoes. After sometime it caught on how much value could be had from canvas shoes. Everyone had to have a pair. Especially when someone learned how to jerry-rig old tires in to soles. Oh black is the best color. You could do anything in them. Dirty them up and all you had to do was rinse them and occasionally use charcoal to dye the black back on."
After awhile of hearing this I still wasn't sold. Then he told me they used to wear them with suits and odd jackets. He said they were smart enough not to look out of place, cheap enough that everyone could afford them, and were multipurpose. All those reasons are why they wore them in such a manner. I also think the lightweight helped in a humid environment like, where my Dad grew up.
Summer time is the best time to pull these on and give it a try. Stick to blazer combinations, light colored suits, and stay away from formal clothes. The shoes are versatile; I'd wear them with a khaki suit or jeans and a dress shirt. Now, in regards of what colors conservative dandies should stick to the trinity of blue, red, and black. Adventurous dandies only your mind is the limit. I've just ordered a pair in peach so, I suggest you push your boundaries and explore an exotic color. After all, most pairs can be had for well under $50. These will be some of the cheapest shoes you'll ever own.
These following gentleman all could wear canvas shoes in the East African tradition:
This is the kind of suit that I would wear with a pair of navy or black canvas shoes; linen is a summer cloth that works with the casualness of the canvas shoes. Keep everything just change the shoes.
Tan suit would work well with any number of colored canvas shoes. I'd just as easily go with brown, oatmeal, or a pale orange.
This is the most prized of occasions to wear said shoes while lounging leisurely in a sport coat and odd trousers. Here I would probably go with a navy or light blue colored shoe.
Here are a few models that merit consideration:
Bright yellow Asos Pilmadrille model. Has the jute sole like espadrilles but is virtually a copy of Keds. It is quite affordable at $30.
Toms in a navy canvas. These cost $48 with tax and maybe shipping a little over the Jackson($50) benchmark. Considering the company donates shoes 1:1 for each pair sold makes it less expensive. These are perfect for the philanthropist in us and the conservative in us as well.
Toms in a madras canvas shoe for $48. This pair is lovely dandified fun for southern gents or preps.
These are true espadrilles that tie up around your legs; the Roberto model from Espadrilles Etc. For the brave dandy, pair with shorts and a French striped shirt while vacationing on the beach somewhere. They are price at $38 from Espadrilles Etc.
Warning: Like most modern mass marketed goods these usually have some logo tag on them. They are quite easy to remove and pose no serious trouble to remove. Also, do not have them resoled from old tires; it is not safe or ideal for dandies to pursue thriftiness to such an extreme manner.
UPDATE: I can no longer recommend Asos canvas shoes. They have plastic sole grips and I am concerned about quality. Since I have never owned a pair, I cannot in good faith recommend them. Plastic in shoes is generally a sign of poor quality construction; I do not know if this maxim is true for Asos. For their sake I hope not.