Colors. Piece by Piece

Cropped Yellow chinos with a "low top" shoe. well done

Your Yellows, Reds, Blues, and Greens all accent each other. Striped top with a solid bottom or vice versa.  Its never ok  to look like a picnic, so choose your Plaids wisely. I prefer Polo because they have plaids that are easily matched. 

New Era fitted caps are an essential accessory, there's no need to collect them all but a Solid Black *White Sox or Solid Blue *YAnkee or a Solid Red*Nationals cap are easily matched with comfortable casual wear.

Casual Day & Night.

The Woven Polo shirt can be worn from Work to Lunch then to the club its very Versatile. A light TAn jacket could be added on cooler night and this look could still be pulled off.

The Classic Herringbone pattern in the driver hat compliments the Office Blue.

Everything doesn't have to be name brand but if your outfit is thrifty then a great accent would be some Expensive shades, but remember keep your logos and designer prints to a minimum. 

Ripped or Distressed jeans can add ruggedness to an otherwise dressy outfit. This look could also be pulled off with a darker slack  either  dark blue or a olive. The Desert Boot is a  very good look, comfortable and stylish -- -- wear and tear is acceptable.