The oxford is the most classically cool and versatile of all fall/winter casual shirts; you should definitely own a few.
Oxford shirts are generally made of thicker cloth and are meant to be washed, tumble dried and worn with some relaxed swagger. They go great with corduroys, cardigans, brogues, dark blue jeans and heavier, "country" style blazers and suits. More of a whiskey shirt than a martini shirt, you can wear them untucked so long as you don't have a jacket on.
Always buy an oxford shirt with a button-down collar. Some brands make oxfords with semi-spread collars, but frankly I think the look is wack.
For an entry-level oxford, I recommend Uniqlo's long-sleeve model. It comes in a nice mini rainbow of colors (such as salmon, lilac and canary) and wears well after a few washes. It is so reasonably priced that you can afford to buy three or four at once and be set for the season. This is a superior product for a mass-market brand, so stock up and maybe explore some funky new shades besides blue.
For the heads out there who want to really own the look, be sure to get something with a nice soft collar. If you want to know and feel the difference between a $30 oxford and something with a bit more refinement, you should touch the fabric on the collar. A well-made shirt will have a lot of give and bounce to it; avoid a cardboard feel.
Unlike a dress shirt, which should be firm and pressed, an oxford shirt's collar needs to be somewhat slouchy and chilled out. A Brooks Brothers slim fit model (the wonderful, utilitarian Budweiser of modern oxford shirts) has a beautiful roll to it that many say can't be replicated. Be sure to get the slim fit model, as Brooks’ standard OG cut is very, very generous and probably not the look you are going for unless you are 56 and running for Congress.
As with any shirt, you don't want to rock this too tightly on some pizza bro hipster shit. It's really easy to take in the sides and sleeves if the next size up fits nicely across your chest and shoulders. If that's too much work, just find a brand you like and buy a few.
About the Author
Elliot Aronow is a tv personality, editor and music and style hustler living in New York City. He is the host/producer/editor/publisher of OUR SHOW with Elliot Aronow and the Co-Founder of music site RCRD LBL. All of his hair and opinions are his own. Follow Elliot on Twitter @youngelz. Check out the rest of his Playboy.com Self-Styled columns HERE.