Business Casual Outfits That Take You From The Work Day To "Off The Clock"

A solid color shirt worn with a solid color pair of pants, creates a simple look for business/casual office situations and the happy hour get-togethers that follow. To finish it off, you need footwear that can hold its own. The versatile style of a classic chukka boot, like the Highland, takes this two-tone look to new heights.

When dressing office casual, an untucked plaid shirt and faded jeans is about as casual as it gets. Thanks to its clean design and classic appeal, a modern chukka boot like our Uptown is the perfect way to dress up this look. These boots play a major role in giving your outfit the style boost it needs.

An untucked shirt, with rolled up sleeves and fitted jeans (also rolled up just enough to expose a sockless ankle) creates a cool-casual look for the most casual office environments and any local night spot. Add in a cap toe oxford like our Postino to give this relaxed outfit a touch of sophistication.

A timeless look that’s right at home in the office or your favorite after-hours spot, you can’t go wrong with a pair of fitted chinos and a button-down shirt. It’s a simple, clean look that is further complemented by a cap toe oxford like our Amelio. Classic yet contemporary, a cap toe works with almost any outfit, making it one of the most versatile shoes in any man’s wardrobe.

Casual doesn’t get any more so than chinos, a white t-shirt, and a heavy cardigan sweater. A modern wingtip like our Castellano fits right into this image but works just as well with a suit, dress shirt, and tie. It is hard to get any more versatile than that.