How To Choose The Perfect Pair Of Overalls

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If you’re like me, you’ve tried on numerous overall styles and been disappointed with how they looked on you. Either the top part was meant for someone with a way longer torso than my own or the legs were just a little too relaxed to be okay. It’s funny to think this jumper style is back on the streets, as I remember my mom gardening in an old pair of Levi’s in the early 90’s. I mean, they might have been more of just a gardener’s style back then, but I would KILL to get my hands on those puppies now. Probably minus the layers of dirt caked on the knees.

There are two types of looks one can go with when wearing overalls: the “relaxed” fit look or the “tailored” fit look. Most overalls fall, for the most part, into one of these two categories. Both are a great alternative to jeans or a dress and are 2015’s version of an everyday romper. Now, how to choose.

The relaxed fit: Think of what you would do to find a great pair of boyfriend jeans and start there (take a look at my how to guide here). A rule of thumb is to show a little ankle. This keeps the bottom part from looking “dumpy”. Next, make sure the waist tailor’s in, even if just slightly. That way, no matter how relaxed the bottoms are, you show the femininity of your waist. The great news is, the top part can usually be tightened or loosened, to your desired fit, so focus on the bottoms first.

The tailored fit: This the style I’m wearing in this post, and have found that in general, this style works best for my body. The legs should fit like a comfortable pair of your favorite jeans, and the more stretch in the denim, the more comfortable these will be. With a fitted bottom, you can relax the straps at the top for a more casual look, just make sure the waist hits you in the right place. The key to this style is thinking about it like you would high waisted jeans.

And the best part about overalls? There is so much room to play. Pretty much any shirt, tank or crop top looks good with them, and when you find the right pair, just have fun with it!

Photography by Ashley Streff

Sunnies: Garrett Leight California Optical

Overalls: H&M (SO affordable!)

Tank: Theory

Sandals: Zara (similar here)

Bag: Mansur Gavriel

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Chelsea |

Thank you, Christine! Stay tuned for a lot more how-to styling & buying tips!