How to Wear Overalls – Styling Tips and Tricks to Avoid Looking Like a Farmer

May 3, 2019

Well you all, it’s official, I have a legit obsession with overalls. I now own THREE pairs. To be totally honest, I want more too. I saw a short pair in camo that I’m really coveting. It all started with this black pair I first shared here. Then I bought the skinny regular pair so I could twin with Ivy Jean (seen here). When temps started warming up, I bought short overalls that I am now sharing below. I cannot stop!! They are just so dang cute.

Not to mention, they are totally functional for me as a mom. It’s often rare when I find something that it cute AND functional. I have had some styling questions from you all about them. Today I thought I would share some tips on how to wear overalls. Let’s be real, people often associate overalls with farming. They can go bad really quickly. Read on for lots of tips and lots of example photos. As always comment or email with any questions. 

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How to Wear Overalls – Styling Tips and Tricks to Avoid Looking Like a Farmer

  1. For long overalls, go skinny! In my opinion, if you are wearing long overalls, the leg should be skinny. This is the key tip when it comes to wearing long overalls and NOT looking like a farmer. Wearing a skinny leg overall will by default make the overalls look modern.
  2. I also suggest that they be a bit cropped in length, i.e. you do not want them to come all the way to your ankle bone and be full length like a normal skinny jean. 

What Shoes to Wear With Overalls

In my opinion, the best shoes to wear with overalls are casual shoes. By nature, overalls are a casual outfit in the making. See examples of each shoe option in my photos below. 

  1. Sneakers are a great option. This is especially a great choice if you are wearing long overalls and a long sleeve shirt, i.e. if it is a cooler season
  2. Flat sandals are an easy choice as well. This is what I would pair with overalls when I am wearing them in the warmer months with short sleeves or a tank top
  3. Mules can be a good option as well for the cooler months/spring if you want to dress your long overalls up but don’t want to wear sneakers. 
  4. Lastly, you can wear boots. This is a slightly more hippie take on overalls, and I love it. I would recommend a flat ankle boot with your long overalls in the cooler months unless you are a seasoned overall wearer/fashionista who wants to try boots with short overalls in the summer. 

What Shirts to Wear with Overalls

Though you have options when it comes to shirts, my main tip is to keep your top on the fitted side. It does not have to be skin tight, but you don’t want a ton of bulk underneath your overalls, i.e. avoid a sweater or think weight material. Otherwise you will create lumps/bumps under them which is not flattering. I have tried to give as many example photos as possible below. 

  1. The easiest thing to wear with overalls is a fitted t-shirt of any kind. It is what I have the most photos of in my examples below. You cannot go wrong with this option whether sold color or striped. Fun details like a leopard print or a slight ruffle shoulder (both in my examples below) will keep your overalls fresh and modern rather than farmer like. 
  2. In the summer, consider a tank top or even an off the shoulder top for those who want to go bold. 
  3. To dress them up a bit, try a button up top or a cute fitted blouse. 
  4. Vary your sleeve length for the season to make overalls work for different temps and occasions. 
  5. You can add a long cardigan in the cooler months over your overalls for warmth and a cool look. Better to add the layers on the outside. 

Where to Buy Overalls

All of my overalls pictured are from Madewell. I have purchased them both at the actual Madewell store and through the Madewell offerings at Shopbop. Another, more affordable, option I really like is Old Navy. I have friends who own them and they are super cute! Similar to Madewell, they offer the skinny regular, skinny black, and short (here and here). 

Black Skinny Overalls Outfit Examples

how to wear overalls - styling tips and trick for wearing overalls without looking like a farmer, skinny black overalls with striped shirthow to wear skinny black overallsblack skinny overalls worn with button up top and black flat ankle boots

Regular Denim Skinny Overalls

skinny denim overalls with but ruffle sleeve top and espadrilles

Short Overalls for Summer

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  • Reply Miley May 22, 2019 at 11:58 am

    Hey, fashionista! Gorgeous!

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  • Reply LORENA May 6, 2019 at 3:49 pm

    My fave here is the one with the pink puffy sleeve top – it just sparked an idea to wear my overalls with a puffy sleeve top I own in blue πŸ™‚

  • Reply Anya Dryagina May 5, 2019 at 9:18 pm

    Honey, you look amazing! I love your outfits!

  • Reply Laura May 5, 2019 at 5:37 pm

    You look stunning in each and every single one of these looks! Love the black skinny overalls that’s for sure with the pop of colour underneath.

    Beautifully styled.

    Laura xo

  • Reply Akaleistar May 5, 2019 at 2:27 pm

    So cute! I love overalls, but I do worry about looking like a farmer…

  • Reply jadej May 5, 2019 at 7:12 am

    omg i love overalls!! i love your style!!

    Jadieegosh   Instagram HelpGrowYourBlog

  • Reply Allie Mackin May 4, 2019 at 11:17 am

    Oh so many great styling ideas here. Overalls are fun I like both skinny and wider leg styles. Though currently I do not own any. They can be tricky to style and longer ones are uncomfortable on me b/c I have a long torso same with boiler suits it depends on the cut. But the shorts are much easier for me to wear and I want to get a pair this summer. You look great in all of your looks!

    Allie of

  • Reply Mercy May 4, 2019 at 10:20 am

    I like your shorts overalls, the skinny look really works. Makes it more cute and well-thought of.

  • Reply The Fashion Folks May 4, 2019 at 7:18 am

    I love how you’ve layered the overalls! The outfit with the leo tee is just so so chic! Xx

  • Reply Laura May 3, 2019 at 2:02 pm

    You look so great in overalls! I have a pair I got last fall and really enjoy wearing them. They are really comfortable!

  • Reply Katherine May 3, 2019 at 1:19 pm

    Ok love the shorter version! They look so cute on you!!

    Katherine |

  • Reply Shelly May 3, 2019 at 11:11 am

    You are too cute!

  • Reply Rach May 3, 2019 at 9:11 am

    These are great tips! You look so cute in overalls!!

  • Reply Rachelle May 3, 2019 at 8:58 am

    you rock them so well, overalls are fun to style.


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