This came up at one of my regular online hangouts the other day. To what extent does one try to match your hat to the rest of your outfit, or even vice versa?
I do try to match my outfits, but I also keep it simple. I try to break things down to either earthy tones (browns, greens, silverbelly, etc.) or grey tones (including blacks). That's about it. Sometimes it starts with the shirt. Sometimes the pants. Sometimes I just really want to wear a certain hat, and it goes from there.
I've gone so far now as to have two different watches (one silver and one gold/brown) and different overcoats (one brown and one black. I've also been buying dress shoes in both palettes. In fact, I've been on something of a used shoe-buying binge. I kind of fell in love with Allen Edmonds shoes when I stopped into their store in Chicago. I can't afford to drop $300 or more on a new pair, but I have been able to find some deals on eBay. The sizing is challenging, but I've had decent luck. I wear custom orthotics, and I have them in various thicknesses, so I can kind of fit a shoe to my foot, based on the orthotic I insert. The orthotic is also nice because it gives me a buffer between my foot and the used insole.
With the influx of nice shoes, I often find myself leaving the house in a very nice, vintage fedora and a pair of very nice, pre-owned shoes. What's in between isn't very fancy, but I figure the extremities earn me some slack there.
Back to work. More poor-writer fashion advice another day.