10 Menswear Items That Are Perfect for Work and Play

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Cotton or wool-blend crewnecks are generally a semi-formal no-no due to raglan sleeves and elastic hem, but that doesn’t mean you have to go all James Bond with a suit and tie at your workplace. This jumper from Margaret Howell gives you a fine knit, lightweight linen/wool blend with a small, yet highly crucial rolled edge detail. Only your true menswear brethren will appreciate the details when you're catching some drinks after work, but the tailored fit will impress your co-workers in that brainstorm session, too.

Depending on how attached your boss is to the height of collars during work hours, Sid Mashburn’s Band Collar shirt is a great chance to educate him/her. Also known as the mandarin collar, it is easier to wear than the traditional button-down if ties aren’t in your repertoire, but it’s just as versatile because it can be worn under a blazer or bomber, with boots or Balmorals. Whatever B’s you want to wear with it, not a problem.

Blazers and sport coats are tricky little buggers. As a whole, they are a good option for semi-formal attire, but they can fall out of flavor fast if they go too far left or right of the “formal” spectrum. Luckily, Our Legacy always seems to get it right with their slim-fitting Unconstructed Blazer, usually available in a variety of materials that vary by seasonal necessity, like this indigo-dyed Italian Twill version with notched lapel and patch pockets. Versatile features allow you to throw it on with the matching pants for a well-fitting suit, or with a pair of denim for date night.

Just because you may not necessarily be the boss in your immediate workplace doesn’t mean that you can’t look like one. Eidos’ supremely comfy, cozy cardigan is made in Italy using 100 percent cotton. It comes in a neutral color that’s able to complement virtually anything in your wardrobe, and it can be dressed up or down depending on your surroundings. Granted, you probably shouldn’t wear it on a summer day, but you’re a figurative boss so you can do what you please.

It’s not necessarily a question of whether chinos can translate to work and play or not, because that’s a given. It’s about whether they look good and last. Wings + Horn’s famous Westpoint Chino is tried and true. It has proven to be the quintessential long-lasting, easily-transferable chino pant. The cotton twill is virtually indestructible and the welted back pockets add a sleek yet sturdy design element that people might not notice unless you have one heck of a tookus.

If you have to wear hard-bottom, steel-toed formal shoes every day, we’re sorry. We’re sorry that you have to go through that and for the fact that we’re rubbing these Quoddy True Penny Loafers in your face. These handmade shoes allow you to have a little fun with your multi-situational footwear. They come with a “Shark’s Fin” blue suede and crepe sole but also have traditional penny loafer details like the beefroll stitch, as well as guaranteed quality to last. No need to keep an extra pair of shoes in your trunk to avoid rubbing down the soles, because that’s kind of the point with these fully replaceable ones.

If you’re sitting at your work desk wearing a hat, there are probably too many variables to pass immediate judgment on this decision. Nevertheless, sometimes it is vital to your stylish existence to wear a hat to and from your job. However, the hat that you choose from the plethora of options is an essential choice. Stoffa’s Rabbit Felt Rollable Hat is the only option. Okay, it isn’t the only one, but it’s a perfect one for wearing to work. You roll it up and store it in a bag so it’s out of sight, out of mind, and out of reach from the grubby hands of co-workers—then you take it back out when you’re ready to peruse the city with your after-hours comrades. It will truly cap off your outfit from day to night, pun intended.

Pleated pants are the bee’s knees again, so while it’s time for you to get with the program, there is a certain protocol that you need to follow in order to be able to wear them to work and to play without looking like a corporate lame-o or zoot-suiter. Maison Kitsune’s Wool and Mohair Classic Pant gives you the neat, pleated look that you need in order to be considered “business-minded” and “employable,” while the cropped hem says that you’re comfortable wearing shorter pants because they’re cool and so are you. The only caveat is that unless you’re wearing nice socks, the ankle-exposed look is recommended.

Chelsea boots are so hot right now. And how can you not appreciate a laceless slip-on boot that can be dressed up or down with the easiest of ease? Of course, there are more “professional” looking versions compared to these Common Projects Black Leather Chelsea Boots. However, the contrasting pull-tabs and crepe sole add just the right amount of stylish flair that easily transfers to the streets, but co-workers likely won’t pick up on them right away. That is, unless you’re “that guy” in the office.

Unless you work on Wall Street or any corporate office in general, you aren’t wearing long sleeves and jackets on every hot summer day. Some employers still require a collar, regardless of the temperature. Polo shirts aren’t always the most stylish short-sleeved, collared option, but nine times out of 10, popovers are. Barenza Venezia’s linen version is a great crossover piece to be worn with a pair of lightweight chinos on days when you don’t want your skin melting off inside and outside of the office.