The culture of the office and its dress code have changed dramatically over the past two decades. This is certainly not news, especially if you were employed during the transition, but for many, the right fit can still be a headache. Indeed, there was a time when dressing for your 9 to 5 was easy: a gray or navy suit with a pair of brogues was always a good bet. Think Mad Men, the wolf of Wall Street, and In the air. These days, however, with Silicon Valley and start-ups across the country promoting a laissez-faire attitude – read: normcore – in open plan offices and boardrooms, the attire prescribed dress is not that simple. Enter casual wear, and more particularly, business casual shoes.
The term is decidedly delicate. What does business casual really mean? What are the parameters? Here is the CliffsNotes version: business, but not too much business and casual, but not too much relaxed. You still want to present yourself in an authoritarian manner, but you also don’t want to be the only dresser in the group. The choice of shoes, in particular, is the perfect way to meander between these two points. If you prefer the formality of a suit, team it with a white sneaker. Likewise, if you like jeans and t-shirts, polish it with the wing tips. There are also styles that themselves fit the business casual bill, including desert boots, Chelsea boots, and certain types of moccasins.
Need more help getting business casual shoes? Check out the selection below. Most of us will be heading back to the office soon (if you haven’t already), and we could all use new kicks when we do. And hey, we can also wear them OOO.
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Stan Smith low trainers
The white sneaker: Adidas and Stan Smith have certainly done it well. If you have a Ludlow costume or something similar lying around, pair it with this true icon.
Penny ‘Hampden’ Loafers
If you’re not looking to overdo the second half of business casual, penny loafers are your friend. Wear it with jeans and a sports jacket, or tapered pants and a stylish sweater, and voila.
Originals 1461 Leather Oxford Shoes
Do you like white sneakers, but feel really good? The Doc offers you slightly offbeat brogues. Pair them with straight, button-down jeans, or a cotton suit, and consider yourself perfect.
Lexington penny loafer
Everything you love about a penny moccasin, reinforced with a chunky lug sole. It’s business and casual in one (very attractive) package.
Chukka Scout Boot
Thursday has a range of casual shoes, but we have a soft spot for Boy Scout Chukkas. Wear them with chinos or dark jeans and call it a day.
Desert Boot
Ah, the desert boot. It doesn’t get any more laid back than that, guys. The shoe is waxed, but not overdressed. And Clarks has pretty much covered the market with its OG version.
Derby Grand Wingtip Original
A wing-tip derby is a pretty formal shoe, as far as office wear goes, at least. But Cole Haan made it a lot more casual with the addition of a grooved rubber sole.
Dev Chelsea Boots
The powerful Chelsea boot comes second after the desert boot in the business casual spectrum. Whether dressing or undressing, this style always follows the line with aplomb.
Capri Onyx Trainers
Still dreaming of a pair of raised sneakers? Try these black leather sneakers from Koio.
Essential low tennis trainers
An ultra-versatile white sneaker with a little something extra, courtesy of Jerry Lorenzo’s Fear of God Essentials line.
Tyler lace up
When in doubt, leather boots are a business staple. Black laces are great to wear with anything black: jeans, chinos, suits, whatever you have.
Penny City Gommini Suede Moccasins Mocassino
Originally designed for highway driving, Tod’s Gommini, that is, the driving shoes, are the kind of shoes that will put your business casual attire into high gear.
Jordaan leather loafers
There are very few situations in which a Gucci moccasin is not the right choice. Go ahead and invest, it will pay dividends.
Suede Chelsea Boots
Speaking of investing, Céline Homme has produced the perfect Chelsea boot for all day. Wear it to the office. Wear it to a festival. Wear it anywhere.
Barry samaha
Barry Samaha is the Style Business Editor at Esquire, where he covers all things fashion and grooming.
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