10 Ways to Wear Pinstripe Pants That Are Anything But Outdated

A must-have staple, from the boardroom to the streets.

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In a sea of micro trends, certain pieces remain classic no matter what. Take pinstripe pants, for example. While they might feel trendy right now due to TikTok’s latest “office siren” obsession, the style is timeless and chic.

Pinstripes originated in early 19th century England. Initially worn by bankers, each financial institution often had its unique stripe pattern to distinguish employees. Over time, pinstripes became a symbol of professionalism, power, and sophistication, spreading beyond banking to general business and formal wear. The pattern gained cultural prominence through Hollywood films, often depicting powerful figures in pinstripe suits. In the 1980s, women’s fashion embraced the style for its polished and authoritative look. Fast forward to today, and this classic pattern has found a place in stylish women’s wardrobes far beyond the boardroom.

So, why are pinstripes so polarizing? The bold vertical stripes can easily overpower an outfit, making it challenging to style with other prints or bright colors. Because of their corporate background, pinstripe pants can appear out of place in casual or semi-formal settings if not styled correctly. The stripes emphasize the fit and silhouette, meaning any ill-fitting areas are more noticeable, necessitating a well-tailored pair. Finally, the typical color schemes of pinstripe pants require careful coordination with other clothing items to avoid jarring contrasts, adding another layer of complexity to styling them effectively.

Whether you’re aiming for a polished look or an off-duty outfit, pinstripe pants can be incredibly versatile. Ahead, we compiled a variety of outfit ideas to help you incorporate pinstripe pants into your wardrobe.

Power Suit

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Lean into the origin of pinstripes and opt for a three-piece suit with a twist. Chloe Harrouche’s ensemble features a vest and trousers, finished off with a long coat instead of the classic blazer typically seen in a three-piece suit. She kept things fresh by leaving a button open to showcase her midriff and accessorized with gold jewelry and sleek sunglasses for an elevated look. To top off the outfit, a sizable tote bag with a briefcase-like appearance is key, as it nods to the pattern’s buttoned-up beginnings.

Summer Stripes

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Pinstripes are not typically associated with summer dressing due to heavy fabrics and dark colors. But we love a challenge and don’t subscribe to a bifurcated wardrobe. To achieve the perfect summer stripe look, opt for a pair of pants in a lighter fabric such as linen, cotton, or silk. Keep the rest of the outfit light and breezy, by pairing white linen halter top with matching mules. This combination makes the look feel summer-appropriate and feminine. A cheeky handbag and cool-girl sunglasses further solidify that this pattern doesn’t have to be so buttoned-up when styled correctly.

Mix it Up

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Like any pattern, not all pinstripe options look the same, and there’s no reason to be afraid to mix them. Tine Andrea nailed this styling trick by not only contrasting prints but also playing with proportions. She kept the base of the look simple with a classic white button-down, serving as a great anchor for the outfit. On top, she wore an oversized blue blazer with very light pinstripes. On the bottom, she opted for skinny dark navy trousers with thick white stripes. The skinny pants balance out the oversized blazer, while the light stripes on top balance out the bold stripes on the bottom.

Go Retro

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Pinstripes were big for women in the 80s, so why not channel our inner retro corporate energy and lean into it? Go with a vintage twist (shoulder pads optional!) and rock a pinstripe suit with 80s-approved accessories, which can range from big, bold earrings to red leather gloves and pointy heels. Dressed for a promotion, if you ask me.

Off-Duty

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For a casual yet cool look, swap out the jeans for a pair of pinstripe pants. One challenge we often face with this pattern is that it often doesn’t feel casual or laid-back. Blanca Miro expertly dresses down the typically formal trousers by pairing them with a T-shirt, an edgy leather coat, and funky accessories. This outfit could have easily looked great with relaxed-fit denim, but the pinstripe pants elevate it, adding an unexpected element to the overall look.

Oversized

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A large chunk of pinstripe options falls into the suiting category, which can be limiting if your job or lifestyle doesn’t call for a strict dress code. To embrace this print without looking like you're in The Wolf of wall Street, focus on fit. For trousers, opt for an oversized, more relaxed fit. Instead of the classic blazer, choose a vest with a cropped silhouette. Finish the outfit with a pair of sneakers for a finance to fashion look.

The New Suit

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Pinstripes are not typically associated with sexiness, but Courrèges is changing our perspective. The French fashion house has reimagined the pinstripe suit with this matching set. The fabric is reminiscent of the classic blue suit, but the cropped cut of the blazer, slim fit of the trousers, and edgy hardware make these pinstripes cool-girl approved.

Lighten Up

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The classic pinstripe typically comes in darker hues like navy, black, grey, and blue. But there’s no rule book that says you have to stick to those boardroom blues. Why not try a lighter option? A white base with colorful stripes offers a fun and fresh interpretation of the classic pattern.

Gray Area

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Typically, when we think of a gray suit, what comes to mind is boring and bland. But that doesn’t have to be true. Try an elevated suit like this one, featuring a cropped bomber-style blazer and slightly oversized pants. To ensure this look doesn’t feel too “office-ready,” keep the accessories cool with a casual white tank and sleek shield sunglasses.

A Touch of Prep

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Lighten things up for the summer with a pair of linen pinstripe trousers. This light navy pair with bold white stripes, styled with a printed crewneck, adds a nice touch of prep, a top trend for 2024. To avoid looking too country club, take a page out of Bettina Looney’s book and edge things up with accessories like bold red sunglasses and chunky earrings.

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