Long Denim Overalls 2019: 41 Trendy Picks to Shop This Season

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Overalls are the kind of thing we strictly associate with spring- and summertime. They drip with day-at-the-park appeal, warranting photo shoots full of flowers and sun. What many of us don’t realize, though, while we’re fantasizing about all the idyllic Instagrams we’ll snap in our dungarees, is that overalls are actually incredibly warm and fall/winter-friendly. And believe it or not, long denim overalls are among the coziest around.

I first stumbled upon this fun fact during my second winter in New York City. It was frigid for months on end, and I was getting tired of wearing the same black jeans every single day. (Always with fleece-lined tights underneath, of course.) Desperate for an ensemble that would break the monotony while still keeping me warm, I grabbed a pair of black denim overalls I’d bought the previous spring. Floor-length, crafted from thick material, and just roomy enough to allow for leggings to be worn underneath, they were perfectly seasonally appropriate. Not to mention, they paired magnificently with every turtleneck and sweater in my closet—opening up a world of winter-friendly sartorial possibilities I’d had no idea existed.

Though I’d purchased my overalls with spring and summer wear in mind, they proved to be a staple capable of carrying me through any season. Plus, the fact that they’re basically just pants makes them inherently transitional—just switch out blouses (and layer on undergarments) as you see fit.

A go-to that’s as chic as it is practical? That’s certainly something we could all stand to have a little more of in our lives—stock up.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

The slightly cropped, straight-leg cut is as trendy as it is versatile. Throw these overalls over your favorite T-shirt—or your most work-appropriate blouse—and watch the magic unfold.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

The pussybow blouse/denim overall combination is a surprising one—but this Nasty Gal styling proves it works.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

A standard denim overall that doesn’t veer into “train conductor costume” territory.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

For the shopper who wants a blue overall that’s as classic as it is fashion-forward.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Because of course animal print dungarees are on the menu.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

A master class in leaning into your train conductor side without skewing too on-the-nose.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Turtlenecks and overalls make for a no-fail combination.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

About as classic as a long denim overall gets.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Sure to play well with anything in your closet.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

For the shopper who prefers their denim covered in pinstripes.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Let the wide-leg crop live on.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Your favorite skinny jeans, rendered in overall form.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

With an overall this classic, it’s near-impossible to go wrong.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

An overall with a slightly dropped waist—because high-waisted isn’t the only way to do it.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

A Scandi-style overall sure to keep you chic and cozy in equal measure.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Peep the raw hem, though.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Train conductor, but make it fashion.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Dyed such a crisp black you’d hardly suspect it was denim.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Because fans of a wide-leg dungaree deserve options.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Walking proof that “edgy” and “overalls” are far from mutually exclusive.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Light-wash denim that’s actually vibrant? Yes, please.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Oh yeah, millennial pink denim is absolutely on offer.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

For the shopper who prefers their overalls with all kinds of ’70s flare.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Baggy overalls that look anything but sloppy.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Sleek enough to pair with your favorite button-down.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

An overalls silhouette that feels simultaneously retro and fresh.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Those pockets look massive enough to store absolutely everything in.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Worth lounging around in all weekend long.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Because pregnancy shouldn’t preclude you from getting into cozy overall mode.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Mom overalls, done the trendiest way possible.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

A denim jumpsuit you could easily throw over your favorite turtleneck—or wear on its own.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Just cropped enough.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Sure to play as well with your favorite heels as they will with your go-to sneaks.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

A waist that’s stretchy instead of structured? Hell yeah.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

For the fan of a washed-out palette—and an exceptionally skinny overall.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

A touch of kick-flare goes a long, long way.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Classic on top. Retro on bottom.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

What drop waist dreams are made of.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Straight legs that are the perfect length—no cuffing required.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

Dripping with all kinds of grunge-edge appeal.

STYLECASTER | Long Denim Overalls Are a Romantic Addition to Any Fall Wardrobe

For the shopper who wants to do overalls in the least obvious way possible.

 

Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale.

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