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A Guide To Rocking Denim Shirts Like A Rugged Gentleman

Less urban cowboy, more sartorial God.

Listen up. There should be ample space in every guy’s wardrobe for a denim shirt.

They’re versatile enough for everything from the office to the airport and you don’t need heaps of imagination to make them work with everything from chinos to suits.

We’ve collected five looks to give you an overview of the ways you can throw denim shirts at problems: whether that’s dressing for a seven-hour layover, cocktail function, or Groundhog Day in the office.

We’ll show you how to wear it across the seasons and keep you out of hipster bartender territory while we’re at it.

The Beckham Layover Look

Layer it like Beckham

This quintessential Beckham look relies on creating the illusion of being a little disheveled, without looking like someone that other people cross the street to avoid.

Here, Beckham normally opts for a crisp white undershirt, dark jeans, and a lightweight denim button-down. Keep the shirt unbuttoned to contrast with the undershirt, roll up the sleeves, and you can try a little half-tuck if you think you’re as cool as he is running to catch a flight (you’re not, but life’s short).

Dress it up with nicer accessories – a decent sports watch, a beanie, sunglasses, and a silver-buckle belt – to remind people that you’re not a complete deadbeat.

Denim & Suits

Suit up, cowboy

If you’re sick of white shirt after white shirt and want to dress things down, denim has serious mileage for work and cocktail suiting.

Versatility is key here, so wear pale blue denim with a cutaway collar that can work on its own, sans tie. Avoid workman shirts, which suggest you shrunk or lost your other, real work shirts.

Pale blues look best under charcoal and should be paired with a textured tie to complement the denim’s casual nature. Bench the tie and leave the shirt open if your workplace allows or if you need an easy transition from work to pub.

Cocktail Denim

Add a touch of class with the right accessories

The murky world of ‘cocktail dress’ leaves most guys stumped, but a crisp denim shirt can get you out of trouble. Our cocktail look is a simple combination – a short-sleeved denim shirt, smart trousers, and the right accessories.

Keep the shirt to a mid-to-lightweight fabric in a soft weave or chambray that you can wear year-round. Cocktail dress generally calls for a slim fit, but don’t wear anything that looks sprayed on (even if you’re one of those shredded-all-year freaks).

Go for classic tailored pants with side adjusters and pleats, paired with monk straps or loafers. Finish it off with a silver dress watch, a leather bracelet, and tortoiseshell sunglasses if you’re out during the day.

Summer Denim

Add a bit of chambray to your vacay

This fourth option is for when a tucked in shirt and smart pants is overkill, but you don’t want to look like a bloke cutting a path of boozy, laddish destruction through Seminyak on holiday.

Start with a slim denim button-down, white undershirt, and shorts. Keep both shirts proportional in length, unless you aspire to an outfit Fred Durst might have worn when he was cool(ish).

Wear chino shorts – not boardies – and don’t wear shorts that go beyond your knee (these should be burnt discreetly). Nothing too skinny, but a slight taper will stop any dad-on-holiday vibes dead in their tracks.

White sneakers or smart slides (they’re a thing, look em up) will complete the look.

To Double Denim (Or Not)

Double with caution

There’s nothing inherently malevolent about denim on denim. But let’s face it, it’s tricky to master and we can all remember quietly chuckling at some schmuck that thought he could do it (he couldn’t).

When it comes to wearing a denim shirt over jeans, you should maintain a point of difference between the colour and texture. This breaks up the look a bit, and eliminates the ‘country guy in the city’ look that no one can pull off.

Ideally, you should never combine heavy shirting with selvedge denim. Heavy denim on heavy denim reminds us of railroad workers or guys that dress like them, but are actually bartenders. Break it up a little and your look will pay dividends.

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