The New Rules of Business Casual

We've got five stylish work ensembles for you — each paired with the perfect timepiece

The New Rules of Business Casual

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While there are certainly a few professions for which a suit and tie are still vêtements requis (looking at you, corporate lawyers and federal agents), recent years have seen a relatively radical redefinition in what constitutes “business attire.” The rise of the creative class and introduction of Millennials and Gen-Z into the workforce have resulted in a marked shift toward the casual in office dress, with even fusty stalwarts like Goldman Sachs relaxing their previously draconian codes.

But this doesn’t mean that we should all be breaking out the hoodies and going full Zuckerberg — a truly dapper gent knows that it’s not about using this opportunity to dress down as much as it is using it to dress with some more personality. To acknowledge the old rules and then break them in stylish, innovative ways.

And thus we’ve partnered with longtime status quo-challengers Timex to present five snazzy updates on the modern man’s work ensemble, each paired with a handsome timepiece from their new collection.

Because no matter your outfit, being on time will never go out of fashion.

1. The Henley Gambit

Every man should own a grey plaid suit, and not shy away from wearing the whole kit in all its checked glory whenever possible. However, it need not always be the whole kit, as the pants make for a great counterpoint to a crisp white henley. The henley tends to be traditionally paired with jeans or chinos, and thus tucking one into a dressier trouser like this (and adding some matching snowy sneakers) is a pleasantly unexpected sartorial maneuver. Throw an understated chain on your neck and add some black accents via your belt/watch and you’re good to go.

Henley by Goodlife, $98
Trousers by Reiss, $220
Sneakers by Greats, $179
Necklace by David Yurman, $250
Belt by Allen Edmonds, $98
Watch by Timex, $249


The Watch to Match


An outfit like this hinges on a deft mix of the casual and the dressy, so when you push those henley sleeves up (and you should), let it be to show off something like this — the Timex Waterbury Classic Automatic lends a healthy dose of timeless elegance to the look, with a bold black dial featuring classic Arabic indices and a croco-pattern natural leather strap. Bonus: the exhibition case back and addition of a 21 jewel automatic movement to keep you on schedule. Double bonus: it matches your belt.

2. Two Out of Three Ain’t Bad

Your correspondent learned this trick from Alexander Kraft, the ever-dapper CEO of Sotheby’s International Realty France and master of pairing the upper two-thirds of a three-piece with something more casual below the waist — an excellent mix of high and low that never fails to elicit compliments. The suit can’t be too slick and business-y though, you’re looking for something a little more tweedy and collegiate (brown and grey work best). Ditch the tie and get a shirt/pocket square combo that plays off the denim, and finish it all off with a jaunty tassel loafer and colorful socks.

Suit by Suit Supply, $699
Denim by Todd Snyder, $198
Loafers by Magnanni, $450
Socks by Ace & Everett, $28
Shirt by The Tie Bar, $55
Pocket Square by The Tie Bar, $10
Watch by Timex, $249


The Watch to Match


When you’re taking a classic look (see: three-piece suit) and giving it an aesthetic refresh (see: adding denim), you want a watch that channels that same vibe. Look no further than the Timex Marlin® Automatic, a contemporary take on the brand’s iconic 1960s design, featuring a 21 jewel automatic movement housed in a timeless stainless steel 40mm case with domed acrylic crystal. The silver-tone dial and brown leather strap from the S.B. Foot Tanning Company (around since 1872) are elegant versatility all the way, the perfect compliment to a voguish getup like the above.

3. Jeans and a Tee, Elevated

We get it — sometimes you just want to throw on jeans and a t-shirt and be done with it. And while that tried-and-true combo by itself isn’t particularly office-appropriate, a couple key additions can get it there. First and foremost, make sure the t-shirt is appropriately fitted and devoid of logos. Layer a light cardigan in a neutral color (grey is about as versatile as it gets) over top, then opt for denim in a solid dark rinse. Finally, elevate the overall look a tad more by adding a chunky brogue in lieu of sneakers (an equally chunky sock never hurt, either).

Cardigan by Brooks Brothers, $99
T-Shirt by Goodlife, $60
Denim by Wellen, $65
Shoes by Allen Edmonds, $345
Socks by Thunders Love, $28
Watch by Timex, $129


The Watch to Match


With an outfit that hinges on elevated touches, you’re gonna want something on your wrist that adds a nice bit of punch to the proceedings. The Timex Navi XL fits the bill nicely, a bold eye-catching combination of brushed steel and deep blues (great paired with dark denim) inspired by early dive watch designs from the Timex archives. Sporty and casual, but with considered details that elevate the overall feel — and that’s what a kit like this is all about.

4. The Tough Turtle

Opinion of the ladies around InsideHook HQ: the turtleneck is a sexy must-wear for gents this season. In addition to that ringing endorsement, your correspondent would like to point out that the turtleneck is a surefire way to church up a leather jacket ensemble, lending a bit of refined flair that helps it to play better in a professional setting. It’s tough, but classy. Pro tip: keep all your elements to black and grey for maximum impact.

Turtleneck by Uniqlo, $40
Jacket by AllSaints, $525
Boots by Taft, $275
Jeans by DSTLD, $85
Watch by Timex, $79


The Watch to Match


A rugged-meets-refined getup deserves a watch that has both in equal measure — enter the Timex Standard XL, featuring a beefy 43mm case and oversized crown, all done in bead-blasted brass with a handsome matte black finish. Clean, classic styling and easily interchangeable black leather straps as well, all the better to match with your jacket and boots.

5. Suit, Meet Sneaks

Finally, let it be known that business casual need not mean you never don a suit and tie again — one great way to give a typical workaday kit a more relaxed feel is to sub a pair of classic court sneakers in place of your dress shoes. You’ll want to keep the suit on the slim side with a healthy taper to the trousers, and stick with a notch lapel — peak is a bit formal/incongruous for a look this sporty. A knit tie helps keep everything laid-back, extra points for a color that plays off other elements of the look like the sneakers and/or your watch (more on that in a minute).

Suit by J.Crew, $396
Shoes by Adidas, $90
Shirt by Brooks Brothers, $118
Tie by The Tie Bar, $25
Pocket Square by The Tie Bar, $10
Watch by Timex, $119


The Watch to Match


In addition to a 100-meter water-resistant gunmetal case protecting its movement from anything you can throw at it, the Timex Allied® LT Chronograph is a masterclass in sartorial coordination. The navy dial and fabric strap? Keeping things sporty and playing off your tie and shoes. The tan accents across all six hands? A nice nod to the brown of your suit. The classic white of the markers? Back to your shirt and shoes. It’s subtle details like this that really make an ensemble sing and set you apart from the pack.