Business Casual Outfits That Take You From The Work Day To "Off The Clock" | Style Guide Skip to main content
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Business Casual Outfits That Take You From The Work Day To "Off The Clock"

What can I wear to work that also looks good for dinner and drinks after hours? It’s a common question that many men ask themselves. It’s not always easy to find men’s outfits that work for both occasions. From business casual to pure business attire, we’ve put together a guide of easy style tips. So whether you are looking for casual outfits, dressing for work or both at the same time, we’ve got you covered.


The featured image is a guy walking down the stairs wearing the Uptown Plain Toe Chukka Boot in Cognac.

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.


The featured image is a model leaning against the wall wearing the Postino Cap Toe Balmoral Oxford in Burgundy.

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.


The featured image is a man walking on the sidewalk wearing the Amelio Cap Toe Oxford in Cognac.

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.


The featured image is a man sitting on a couch wearing the Castellano Wingtip Oxford in Saddle Tan.

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.


The featured image is a model walking down the street wearing the Belfast Plain Toe Gore Boot in Cognac.

If your look leans toward the dress end of casual, in other words dress pants, a button-down shirt, and crew neck sweater, you need a boot that matches. For the versatility to take you from dress to casual – including this in-between state – nothing works better than a chelsea boot. Our Belfast is designed with that in mind. Featuring an ultra-smooth one-piece vamp and an elongated toe, it has a subtle plaid, windowpane pattern on the side gore that makes it a real standout.

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