How to Layer Overalls (dungarees) in ten outfits

Let’s talk overalls. This post has been a long time in the making. I am a kid that grew up wearing overalls, whether they were Oshkosh B’Gosh or Ralph Lauren, I was always out in my overalls getting as dirty as possible. These days, I’m trying to stay out of sandpits and mud baths with my overalls on. When I’m pairing my grownup overalls with a white linen blazer, you can see where old habits might not work the best with updated wardrobes. So how do we style overalls as adult women? Well, it’s all about layering! You absolutely can wear your overalls into your adult years. Just go watch a few episodes of Grace & Frankie, if you don’t believe me. Frankie is my overalls style icon. She’s goals for my later years in denim. Anyway, we’re not here to examine super celebs and their TV outfits. We’re here to talk about how you, Miss “I need this for everyday practical wear,” could use your overalls in outfit planning! It’s all about layers. Once you start playing with a few ideas, you’ll find overalls aren’t scary at all. You just have to think outside the box. So to get you started, here are ten outfits that I’ve worn over the years, with my overalls, that have never led me astray.

Before we jump into the outfits themselves, let me suggest a few places to get overalls to adore and cherish.  I will cover every size group, so keep scrolling until you find you. Also, please note that affiliate links are used in this post!

I will start with the overalls I’m wearing. The exact ones are no longer available, but the retailer has a number of options. I trust this company implicitly. I have always bought my jeans and overalls there and cannot say enough good things about them (ps they go up to size XXL/22):

These are the regular size overalls (many coming in lengths for petites and talls and up to a US size 20):

These are the plus size overalls (dear retailers…. please make more overalls for plus size!)

Alright, now that we’ve got the “how do I buy my overalls” out of the way, let’s look at how we style them. I won’t drone on, just a few sentences about each look!

You can also watch the video for styling, if you’d rather see things in motion. This was originally on stories, but people were asking for a permanent place to watch and save, so I’ve put it on youtube for ya!

Look one:

The Formal Way to Wear Overalls

If you can believe it, overalls have actually made their way onto red carpets several times. While I wouldn’t be so brave, myself, I do think you can dress up overalls, without a problem! I’d wear big old black heels with this look, but sadly all my heels are now in a storage unit in London, so I’m opting for sparkly flats instead. The key here is the designer black tuxedo jacket. It’s Jason Wu and it instantly elevates the look! Paired with a silk blouse and some chunky earrings, I love this look for a night out with friends. If you’re missing any of these wardrobe staples, here are a few suggestions.

Look Two:

Going Nautical 

I love a nautical look, in any form, but with overalls it’s chic as hell. I’m wearing a simple knit blazer over a classic breton striped tee. As it’s summer, I’ve paired with a slim silver sandal. Done and done! Also, this outfit is insanely comfortable. Just saying. Overalls and comfort, who knew?

Look Three:

The Canadian Tuxedo

Aw, double denim. It’s controversial, but only because of that darn moment with Britney and Justin. If that hadn’t happened…. The Canadian Tuxedo would be living strong in every wardrobe. I’m trying my best to make sure double denim never dies. Yes, even in dungaree form!

Look Four: 

Autumn Seaside Strolls 

I have to shout out Winser London, who are responsible for creating this beautiful sweater set. If you don’t know about this brand, get involved now (reasonably priced and well made wardrobe essentials galore).

So this look is more about pairing a matching sweater set with the overalls. And let’s talk the belt for a second. For me, the belt brings the look together, but is not very flattering from the back. So, I’ve worn an oversized cardigan to cover the unflattering bits. I wore this outfit endlessly last time I was in Maine in October. It’s comfy, warm and oh so put together!

Look Five:

How I’d Imagine Ralph Lauren Would do Overalls

Let’s just call this my ode to Ralph. The blazer is actually vintage Ralph Lauren, so it feels right. This is actually an outfit stolen from how I love to wear this blazer with jeans, pairing it with a grey top and trainers. Easy peasy!

Look Six:

Winter Wearer

This is definitely one for chillier weather. It’s all about layering similar colours with a knit and a coat! The combination is pure comfort magic. Jazzed up with a leopard flat, this is heaven in overall form for days when you want to feel like you’re out and about wearing your duvet… only it’s dungarees!

Look Seven:

The Bomber Babe

Borrow a shirt from the man in your life, score a vintage bomber jacket from local thrifting and pair with a wacky pair of heels and you have one of the best looks to work with out of the bunch. This look is all about fun with style. Pair as much colour and textures as you can to make the outfit even louder and more fabulous!

Look Eight:

The Summer Suit

This is my summer favourite. I feel so chic when I step out in this look. The linen blazer is key and it has to fit you perfectly! Pair with any white shirt underneath, button down or simple white tee, and give the outfit a bit of flare with animal print flats!

Look Nine:

The Statement Sleeve Sip

The world is obsessed with statement sleeves at the moment, as they should be! It’s a look. And it’s one that doesn’t have to take a back step to your overalls look! Embrace the statement sleeve and dress it up or down accordingly. This look, I dressed down with a tied denim blouse around the waist, but gave additional life with the colour pop slides!

Look Ten:

Pretty in Pink

The simplest of the bunch. Just grab pink and layer. Can’t go wrong. If I had more time, I would have found pink earrings and bracelets to match! Remember, it’s all about layering and don’t ever let anyone tell you “less is more” 😉

And there you have it, lovelies! Let’s hope this gives you a little push to make the move to including overalls in your outfits going forward! Sure, they are a pain to get in and out of in bathroom situations (no point denying that), but they are so chic they’re worth the extra effort!


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