How to wear overalls: 10 street style tips for turning this farmer staple into the ultimate fashion statement

Date August 13, 2014

Once in a fashionable blue moon there is a happy coincidence between the trend du jour and comfort. Luckily for style devotees, this season is rife with such coincidences. The must have items range from bedazzled Birkenstocks to roomy menswear and now we can add the ever-practical overall to the list.

First seen back in the early 1900s, the overall has weathered the test of time. In the ‘80s and ‘90s, the overall took flight as the It item for everyone from Will Smith in the Fresh Prince of Bel-Air to Jennifer Aniston’s iconic Rachel on Friends. Have no fear though—today’s overalls are anything but a bad high school flashback. Goodbye frumpy mom’s version—hello to overalls in sleek leather and bold prints.

So, how to wear overalls while making them look modern and totally grown up? It’s all in the outfit pairing. Pretty much every one of our favourite looks featured below favours a plain shirt or a crisp tee underneath, elevating the look to office-appropriate territory. No longer should it be passed over for being frumpy or dowdy—the latest looks from the street prove that the overall is one of the hippest pieces to own.

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How to wear overalls

When you want to show off your toned legs but it’s a breezy day outside, shorts overalls are the perfect solution. Keep your top ladylike and prim to avoid looking childish. Matching your bag is just an added bonus.

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How to wear overalls

Life truth #459: Models are the ultimate trendsetters. Grace Mahary rocks a bold floral print overall showing the overall’s versatility and ease. This is the perfect piece to throw on for a busy day running between fashion shows (or in the case of us mere mortals, meetings and coffee dates.)

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How to wear overalls

For a vintage ‘90s look mix your leather overall dress with a slouchy tee and a tied plaid shirt. Keep it modern with eye-catching hardware, fastenings and accessories.

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How to wear overalls

Optic prints are all the rage for Fall 2014. Get the best of both trends by merging them in one glorious piece. When doing an all-over print, matching shirt not required, keep the silhouette streamlined and fuss-free.

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How to wear overalls

If you scour your local thrift shops for a pair, more often than not, you’ll end up with a vintage fit like these ones. Embrace the retro shape but keep things fresh with modern accessories and simple hair. No scrunchies or hair bands allowed.

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How to wear overalls

The mod hardware and luxe fabric of this overall dress makes a high-statement outfit out of one bold piece. If you source your pair from a thrift shop think of switching out the hardware with some colourful ribbon or sleek metal fixtures to update the look.

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How to wear overalls

A patchwork denim overall is best done in clean graphic lines to avoid looking like a bad retro throwback. The black sleeveless top and leather jacket are the perfect backdrop for the artistic vibes of the overalls.

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How to wear overalls

If overalls are only one part of your grunge-inspired look, why not layer ’em under a borrows-from-the-boys button down or raincoat.

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How to wear overalls

This overall-inspired frock is one-part lederhosen and 10 parts cool. Dresses with a lower bib and adjustable straps are a grown-up way to get in on the trend.

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How to wear overalls

Changing up the cut of your overalls is the easiest way to update your look. A tapered leg and a dropped waist are completely Euro-chic and totally hip. A slim leg or cuffed hem works great with a killer pair of heels.