DavidT Board

Shoes

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Allen Edmonds Mojave Desert Boot: You’ll want these in one of the suede versions instead of the regular leather. Similar to the other chukkas but they’ll fit and they’re of a higher quality and will last longer. $295

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Allen Edmonds Park Avenue Cap Toes: The little line of stitching that creates the cap is what separates these from something as formal as opera pumps. That being said, they don’t have any of the broguing common on other shoes so they won’t look too casual either. $345

Shirts

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Carhartt Slim-Fit Chambray Shirt: While it is a slimmer fit, it’s designed for men of your build. A chambray shirt should probably be one of the Staples on my list. They’re so versatile and are a great way to comfortably wear something that has a Rugged connotation. $48

Cutter & Buck Ferris Wheel Gingham Shirt (aff link): This may be one that will need some alterations from the start, but the pattern and coloring are too good for you to pass up. The size of the gingham is perfect, as is the contrast between the different colors. They’re obvious without being so strong that they’ll wash you out. $95

Pants

Rodd & Gunn Broadfield Oldsquaw jeans (aff link): Should be easier to find than the Fidelity jeans but still accomplish the same goal. They’re roomier while still maintaining the shape of slim jeans and the proper, inky blue color that allows them to be dressed up or down. $125

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Gap Lived-In Slim Grey Khakis: The lived-in khakis have also been fairly well fitting for guys of your size. The grey color is neutral – so you’ll get a lot of wearability out of these, but it’s also a cooler shade – so it will be better with your coloring than the traditional khaki color. $70

Misc

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Goorin Zanpa Hat: With your build and your lifestyle, finding a hat is going to be a bit difficult. The fedoras you see on most men give off a forever-alone impression, and a baseball cap will end up being too casual. Something like this linen gatsby cap has a brim to help keep your face covered, but also has a shape that’s unique enough to show that you’re intentional about your clothing. The fact that it’s linen means it won’t wear too warm in Arizona either. $58

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Seiko SNK805 Automatic Watch: This might be the solution to your problem. Automatic watches self wind with the movement of your wrist and other daily motions – meaning there’s no battery for you to mess up. I like the casual, rugged look to this and the nod to your military history. $185