How to Wear Overalls Without Looking Like a Farmer

How to Wear Overalls Without Looking Like a Farmer

Overalls, Really?!?

When I was in my 20’s and early 30’s I lived in, and lived for, a good pair of denim overalls. One of my favorites was a pair of size 16 from GAP kids I scored for $ 19.99, let’s just call that one of the benefits of being under 5’4″.

Then during my maternity years, overalls were a staple in the waxing and waning of my childbearing belly. 3 kids in 4 years and a 70 lb weight gain with each (yes, you read that right, scary but true) made them basically a necessity.

How to Wear Overalls Without Looking Like a Farmer

So, needless to say, overalls have a special place in my heart. Whenever I’d see them in a store I’d try, keyword here is TRY, to make them work. In the past they just make me feel like a wannabe teenage farmer – NOT the look I was going for – so I’d pass.

Kind of like the pair below. I posted it on my Instagram feed in March of 2016 – that’s when overalls were just starting to make their way on to the scene and into the stores. There was a hard pass on that pair, and those of you that followed me back then HATED them.

But, this year, We are LOVING them! For Real!

Recently, both Elana and I have been crushing on the whole overall, coverall, flight suit thing. They’re kind of like a jumpsuit, so it has the ease of all-in-one dressing.  But it’s a bit tougher than one made of silk. So it gives that uncomplicated, effortless, je ne sais quoi vibe. AND it easily transitions from sporty to cocktail just with a change of accessories.

Before you say NO WAY… hear us out…

The RULES for pulling off overalls, coveralls and flight suits.

  1. They’re just hitting the mainstream. Wearing a one-piece “utility” type suit is definitely for early adopters right now. But we are seeing it gain a lot of traction. Even if you’re not ready to pull the trigger, keep it on your radar. Kind of like how we told you about sock booties 3 years ago – we’re letting you know about it early so you can opt in when you’re ready.

  2. DO NOT pair them with a plaid flannel and cowboy boots or you will feel like Old McDonald.

  3. Make them look effortless and chic by wearing them with a heel (boot, sandal or pump – but a heel) and a slim top underneath. For the winter make it a turtleneck and boots like Hallie did above. And in the warmer weather a sleeveless ribbed tank, an old favorite that feels totally new again and pumps.

  4. Transition them from day to night with accessories – flat sandals and a cross body bag for daytime, heels and a clutch for night.

  5. If you want to wear them with sneakers, make sure to show some ankle. And also know it gives off a “younger” vibe. You can do it if you’re 40+ but just be mindful of the other accessories you’re wearing. Like don’t add a backpack to the mix or someone might ask if you want a juice box not a bloody mary.


My Favorite Overalls, Coveralls, and Flight Suits (also called Boilersuits)


Some Overall Street Style Inspo:

Oversized denim overalls

Image via Free People

Leather flair overalls

Image via Revolve

Black denim overalls

Image via Madewell

Slim leg blue denim overalls

Image via Old Navy

Are you feeling inspired? Did you wear overalls in the past? Think you’ll try them again? I honestly didn’t think I would, but I’m loving them!


Outfit details: Overalls  run small, size up // Turtleneck // Boots run tts // Bag reversible and under $100

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