/6 Ways To Wear The Same Trousers Every Day

6 Ways To Wear The Same Trousers Every Day

Successful men often find a uniform and stick to it. They also live on a diet of liquid meal replacements and wake up to train at 4am every morning, but only one of these practices we actually endorse.

By removing the need to choose a completely new outfit each morning, your mind is freed up to focus on other, more pressing issues. Sounds a little mundane, sure, but it’s easy to see the argument for choosing one key piece – a pair of grey trousers, for example – to base your weekly wardrobe around.

“Grey trousers are a staple for good reason,” says William Counsell from independent tailoring brand Cad and the Dandy. “They can be dressed up with smart separates or down with T-shirts.”

So make like Dr Dre, Mark Zuckerberg and Barack Obama by learning how to make a single pair of grey trousers work from Monday to Friday right through to Sunday without breaking a sweat with these six looks.


A Lazy Start

The start of the working week is mostly spent replying to emails and avoiding as much human contact as possible, but that doesn’t mean dressing like you’ve already given up. Smart (or at least, smart-casual) attire will distract colleagues from your slightly bleary eyes.

A white grandad shirt is an excellent piece of Monday morning subterfuge. When cut slim from soft cotton poplin, it can look just as smart as its collared brethren while feeling much less restrictive.

On cooler days, layer your shirt underneath a crew neck jumper that will accentuate the collarless design. Navy or black are both solid choices, but something in a less common moss green or one with a graphic design can help inject some much-welcomed life into your look. To bookend this outfit, keep things smart with a well-polished Derby shoe.

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Down To Business

Now that the sins of the weekend have been washed away with copious amounts of coffee, it’s time to put your best foot forward and show you mean business.

Grey trousers worn with a navy jacket is a classic separates combination that’s never not in style, though you might also choose a deep oxblood red or something with a subtle check. The monochromatically-minded might want to opt for something simpler, but steer clear of black unless you’re aiming for a more formal look.

Whichever colour you choose, aim to maintain a similar weight of fabric throughout your outfit, ideally with a similar matte finish, and make sure that there is a clear distinction between the two shades. Finish with a slim-fitting grey roll-neck in winter, or else a white shirt and understated tie pairing. Now you’re ready to boss the boardroom.

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Grey On Grey

In complete contrast to Tuesday’s well-heeled showing, sometimes the hump-day requires a more low-key approach to dressing.

The formality of your trousers means that you can get away with a relatively laid-back top-half. A slim-fitting pastel sweatshirt barely registers as sportswear when worn in place of knitwear, especially if layered underneath an unstructured blazer. If a collar is non-negotiable, you can easily slip the basic over a button-down shirt, but leave the tie in your drawer for another day.

Clean white sneakers complete this understated outfit, but they can easily be substituted for desert boots in a pinch. Keep a leather biker or bomber jacket on the back of your desk chair to throw on at the end of the day, ready for a mid-week date night.

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Modern Preppy

As the working week begins to wind down, you might be tempted to take a lengthy working lunch or to down tools early for a spot of alcohol-sponsored team-building.

Decoded in menswear speak, that means what you require is something that is office-appropriate, but won’t look out of place at the bar. A preppy look straight out of the 1950s is the way to go.

A simple cardigan the perfect piece of smart-casual wear for this very scenario. The V-shaped garment is a classic, understated choice, with all the substance and framing effect of a lightweight blazer but none of the structure. For authentic Ivy League style, choose a shawl collared design in collegiate red or blue, to be worn with a white Oxford shirt and the obligatory suede loafers or driving shoes.

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Drawing The Work(wear) Week To A Close

With the bright lights of the weekend in sight, a few after-work pints feels almost obligatory. To dress for this, look to the holy grail of workwear: the chore jacket.

A modern, utilitarian alternative to other classic outerwear styles, the boxy shape will be offset by the slim cut of your trousers, and can be further bolstered by a judiciously-tucked in T-shirt. Navy is the traditional choice, but you can also play with off-white or khaki to keep things tonal.

Down below, retro running shoes are the obvious choice here – stick to low-top styles that show off a hint of colourful sock underneath. If sneakers aren’t an option, try a pair of lace-up boots that just graze the ankle.

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The Weekend

Cuban Collar Cool

With the weekend comes the opportunity to loosen things up, and few pieces help do it better than a Cuban collar shirt.

The mid-century staple is a perfect companion to a formal cut of trouser, creating an off-duty look that still feels polished. Better yet, because the neutral grey of your bottom half serves as a blank canvas, you can wear colour and print with abandon. Florals and Hawaiian landscapes are particularly apt for the warmer months, while vertical stripes and block colours can have a slimming effect. Wear yours over a plain white T-shirt for lazy afternoons in the pub, or try buttoned-up and tucked-in for Saturday nights on the town.

If your trousers are part of a lightweight suit, you might even consider wearing the shirt underneath a blazer when summer wedding season hits, with a pair of penny loafers or horsebit slippers.

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Grey Trouser Checklist


For one of anything to work in multiple ways, it needs to be versatile. In the case of grey trousers, that means opting for a light to medium weight wool in a plain, matte weave. “You’ve heard it many times, but wool really does keep you cool in summer and warm in winter,” says Toby Lamb, design and brand director of Savile Row tailor Richard James.


One size rarely fits all, but in this case, one fit might. “Slim but not skinny is most flattering,” says Reiss menswear director, Alex Field. “Make sure you feel comfortable around the waist and seat area, and that the knee and hem are tapered for a contemporary feel.”


Any man who has ever poured himself into skinny jeans one season, only to be saved by wide-leg trousers the next knows that trending cuts often change, but now is the time for consistency. Stick to flat-fronted trousers with a medium rise over anything pleated or high-waisted. “What you want is a classic style that is going to remain untroubled by the vagaries of fashion,” explains Lamb.


When it comes to a trouser length that can fly with sneakers as well as Derbies, the aim is to hit the sartorial sweet spot. “A slither of ankle looks smart with a shoe or loafer but equally cool with a sneaker,” says Field. “You might try a turn-up, but be warned that this doesn’t always work for formal situations.”

Care Instructions

Any garment worn for consecutive days is going to need some TLC, but keeping your threads fresh is made easier when you shop smart. Look for a pure wool or wool-blend fabric that can withstand being ironed every other day and thrown in the wash at the end of the week.