From back in the days of riding my Powell & Peralta skateboard on the streets of lower Manhattan, Vans footwear has been de rigueur among the skating crowd. Some 20+ years later, I have about 3 to 4 pairs in my closet, ready for their debuts (I tend to introduce a pair to the world every summer).
The style of shoe I prefer is the Vans Authentic and/or Era (available at www.vans.com), which comes in a variety of vibrant colors, textiles, patterns - basically they got something for everybody.
I've rocked my Vans Authentics (in red) since last summer - and have gotten tons of compliments ever since.
I feel I can safely say that (to me) there isn't a better-looking canvas sneaker out there, except maybe the ChuckTs or the JPurcells. However, the Eras aren't so mainstream that you look like the "many" in a crowd, rather than the "one".
So, if you got about 40 bucks in your pockets, cop a pair, wear without socks, they go great with basically anything you put on above them.
For your enjoyment, a picture of my crown jewel, Vans x Supreme collab - Eras....(yes that's denim with checkerboard!)