Taylor Stitch Jack Oxford
Credit: Tom Schierlitz

We're never going to tell you to be a man and wear pink to the office. But we will tell you this: If you want to look your very best from nine to five, pick up a dress shirt like the Taylor Stitch Jack Oxford, which remains consistently slim through the chest, stomach, and waist. Made in San Francisco, the Jack has a shorter cut than most modern oxfords, meaning you can wear it tucked in or out without looking slovenly. Its tailored profile prevents that all-too-familiar blousy effect, while the old-school, all-American button-down collar will never go out of style. Plus, an absence of pleats makes for easy ironing (but we think it looks its best with a few wrinkles anyway). [$125; taylorstitch.com]