Colorful Shoes

Add some variety to the brown leather/white canvas footwear mix with some colorful shoes.

There are plenty of options available in a range of styles. I particularly like these boat shoes by Sperry:

You can't beat such vibrant colors that still retain a sense of classic style. The blue, in particular, would look great with a pair of chinos or white denim. Even better, these are only going to run you about $80 -- pretty affordable for a very interesting shoe.

Beyond this, you can get some great moccasins in nearly every color imaginable.

The key to wearing daring shoes is that you remember that they're only part of an outfit. Too many people get a pair of really colorful shoes and then wear them everyday with every outfit they have. That will never work. If you want to do that, get a pair of plain sneakers or wingtips. If you want something more interesting, then you're going to have to put some thought into the rest of your outfit, particularly your pants and socks.

As inspiration, this gentleman, who should probably be teaching a class in how to make sweatpants look good:

Take note of how, first of all, the purple shoes look good with the light grey pants. He's gone beyond that, though, incorporating a different shade of purple into his outfit. He pulls it all together nicely.

Just make sure you do as he does and you'll be able to work colorful shoes into your wardrobe easily.