How To Wear Pinstripe Trousers The Modern Way

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If, like everyone else, you have long been confused and frustrated by the smart-casual dress code, base a pair of pinstripe trousers at the core of your wardrobe and you’ll make the job a whole lot easier. The fine-line print hasn’t always been seen as a key piece in a man’s everyday arsenal. For a long time, the pattern was predominantly found on the same-ish suiting of city types and Prohibition-era mobsters. It was a power play. Precise and domineering, but ultimately monotonous because every banker dressed the same way.

Today, the subtle striping has returned with a new and more effective role, away from the confines of tailoring and gangsters and into the diverse world of casual dress. Think baseball jerseys, casual shirting and most notably, legwear. Pinstripe trousers are now as much a part of slouchy tailoring or rule-breaking streetwear as the average Wall Street uniform. Worn the right way, they’re only a few rungs up from loungewear.

The New Rules Of Wearing Pinstripe Trousers

Sure, you can’t go wrong with plain navy or black pants, but pinstripe trousers offer surprising levels of stylish versatility. Traditionally seen in smarter looks, it’s perfect in an office two-piece but it can also carry a certain level of neatness into more casual ensembles, instantly giving your outfit a sharper edge. For less adventurous dressers, it’s also an easy and accessible way of adding a touch of character to otherwise minimal looks.

Zara

There are a couple of simple rules worth abiding to avoid any faux pas. First, avoid accompanying them with more stripes or garish patterns on your top half. That’s just hard to look at. Secondly, keep the complementing palette minimal and pared back. Yes, it’s a subtle pattern, but treat it like you would bright colors or bold prints like camouflage: this is the focal point of your outfit. Keep the surrounding pieces muted and bring in earthy or classic colors like off-white, grey or navy to ensure a neat look.

To wear pinstripe trousers in a more modern way, look for a looser fit around the leg. This has the interesting effect of making the stripes wavy, which instantly makes the look more casual and less straight-laced. Pair them with other smart-casual heroes like a simple sweatshirt and minimalist trainers for a comfortable way to do business-casual.

5 Go-To Looks

Layered Up Top

An easy way to work pinstripe trousers into your everyday wear is to go back to basics. Go for a grey straight-leg cut, miss out the socks and pop on some fresh white trainers for a neat start below the belt. Then, a simple layered look composed of white crew-neck tee under a soft, lightweight navy jumper will complete a Scandi-inspired take on smart casual up top.

Mango Man

Off Duty Tailoring

Although arguably overused in tailoring, pinstripe trousers still offer a level of formality that will appeal to people after a smarter look. The key is to soften those smarter elements by swapping in some more relaxed pieces. That means losing the smart shoes, popping on some minimal trainers, and rolling the cuffs of your trousers to give it a more relaxed feel. No ties needed here, leave a crisp white shirt alone, unfastening the top couple of buttons before layering it under a neat, navy blazer. The darker tone of the blazer up to will contrast the bottom half without fighting for attention.

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Dressed Down Knitwear

Standard winter insulation, three to four layers that include a knitted piece, can be the perfect accompaniment to your pinstripe trousers. Above the belt, take the approach that the lower the layer, the lighter the tone. Go with a white shirt under a cream knitted jumper for a neat, relaxed start. Over the top, button up a beige blazer and finish with a grey shearling-lined jacket. Each layer will offer a slightly different cut and a slightly different shade to keep things interesting. Below the belt, the pinstripes on your slate-grey trousers will elongate your legs and draw the eye down to some classic minimalist trainers.

Brunello Cucinelli

With An Overcoat

Here’s where we see the piece’s true versatility. Roll with fashion’s new love for baggier cuts and let your pinstripe trousers cuddle up to a pair of boxfresh white sneakers. The overcoat always looks at home in laid-back looks, adding just a smidge of business to them. Opt for the jacket in a darker grey than your trousers so as to subtly, yet effectively elevate those trousers to the key piece in your look. For the final touch, throw on a lightweight sweatshirt in a rich blue to break up the monochrome and tuck it in for extra style points.

Zara

The New Suit

If dressing up really isn’t your thing, this is a smart option. Pinstripes bring to make a matching two-piece just as effective and well-styled as a formal outfit, while also giving you the flexibility to choose comfier, lighter-weight fabrics like linen. Relaxed silhouettes are the order here via slouchy trousers and a matching overshirt, left open to show a subtle, off-white top. Simply add a fresh touch to the simplest of style statements by accented your striped look with a clean pair of trainers.

Zara

What To Buy

Casual

‘Pinstripe’ and ‘casual’ probably aren’t two words you’re accustomed to hearing in the same sentence, but things are changing. A general shift across the whole of menswear has resulted in the relaxing of dress codes, the loosening of cuts, and the merging of styles. That means what was once reserved exclusively for 1920s mafia men and ruthless Wall Street bankers are now right at home on a pair of joggers.

Smart

Pinstripe’s natural home is running subtly through the length of a crisp, expertly fitted suit. It was first used by London’s banks to identify their employees among the sea of tailoring in the English capital during the early 1920s and it’s still a sartorial power move of financial elite used to this very day. Team a navy pinstripe suit with a pristine white shirt and a gold wristwatch and command the room at your next board meeting.