Denim Dress Shirt
Not all denim shirts are meant for rodeos. A classic dress shirt cut from denim adds texture and a dash of rugged casual to more preppy or refined outfits. Swap for J.Crew's chambray shirt for a lighter-weight option or more sizes.
A textured but simple style in a low contrast grey. With over 12,000 reviews and under $25, it's a no brainer. Swap for a canvas military belt for a frugal alt.
Swap out your khakis for some off-white twill pants: They warm-weather-ify any outfit and are just as easy to pull off. Pinky swear.
Loafers would look great. Some chukkas, for sure. Or, toss in some small beach town energy with a pair of Vans made with a handsome neutral suede.
A simple, classic field watch at a reasonable price.
A pair of clear frames aren't simply the “go with anything” option, they contribute a surprising amount of style for something so…transparent.