Style Notes: Overalls

I know, I know, I just did an outfits post on those shortalls, but I am still on an overalls kick and have been so excited to explore how they can be styled that I wanted to do a more comprehensive post! I suspect a lot of people have overalls filed away as too childish or utilitarian-casual, but especially with all the different styles you can now find them in, that’s really doing them a disservice because they have so much potential!

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What even counts as “overalls”?

Generally, overalls are a garment where pants are held up with straps via a bib attached to the front of the waistband. But there’s some wiggle room there. For the purposes of this post, these are examples of garments are NOT included when I refer to overalls:

Sleeveless jumpsuits – While also fantastic for layering, these don’t require a base layer for boob coverage. Usually more formal or loungewear leaning, depending on the fabric, but don’t have that distinct blue collar workwear origin feel like overalls (or jeans or coveralls).

Aritzia Jumpsuit

High waisted suspender pants – Again, I think these have more of a 20s/30s/40s/dressy vintage association rather than casual.

Anthropologie Buttoned Pinafore Jumpsuit

Pinafore dresses / overall dresses – A lot of the points here can be applied to overall dresses, but for scope, I’m sticking to overalls with pants or occasionally shorts here. Pinafore/jumper dresses in particular are a sort of convergently evolved item to overalls, and like the other things I think they usually have a particularly sweet/girly connotation which has a different effect than plain old long pants overalls.

Anthropologie Pilcro Overall Skirt

Jumpsuit, Boilersuit, Pinafore, Jumper, Overalls

Pros and cons and things to note

Pros

  • Relaxed or nonexistent waistband – If you want that denim/chino/corduroy pant look but just can’t deal with wearing or finding the right fit waistband, overalls may be an easier option as it usually doesn’t matter that the waist fits exactly.
  • Adjustable – Most cuts are amenable to cuffing and have adjustable straps for more customizable fit than jeans or dresses.
  • Instant “third-piece” effect – Gets you over the “just a top and bottom” outfit blahs instantly.
  • Pockets galore – typically you are guaranteed at least 2 pockets, and commonly a giant pocket on the bib as well.
  • Sturdy – typically made from thicker fabrics, and it’s easy to find options meant for actual physical work if you like your clothing extra hardy.

Cons

  • More annoying to use the restroom – Pretty self-explanatory. Watch out that you don’t accidentally dunk anything.
  • May pill delicate tops more aggressively – Think twice before you wear these with your favorite whisper-soft tee or delicate blouse.

General styling notes

  • You’re not gonna have a defined waist – If that’s something that you need to feel comfortable, there are some more fitted styles available particularly in vintage aesthetic brands or you can go for a moroe flared wide leg style, but for the more traditional cuts, just remember it’s not going to magically conform to your back to show off your figure. You will most likely look like a sack from the side. That’s part of the charm, IMO.
    • Note that contrast in fit if you go for a skinnier fit in the legs will highlight the looser silhouette at the torso.
  • Leans casual – because they are historically a blue collar work garment, the classic blue denim overall will have a strongly casual pull to most people.
    • Easy to pair with other casual pieces – cropped jackets, structured casual jackets like trucker jackets or shackets. Menswear style shoes, pretty much any boot or sneaker, chunky sandals. Chunky cardigans, button down overshirts.
    • May look less cohesive with dainty shoes, dressier outerwear (like tailored wool coats), and thinner cardigans (will be lumpy) without particular consideration to styling.
  • Leans youthful – I’m not sure why (cause it’s hard for them to pull off and the lack of waistband is comfortable?) but for some reason overalls have been a staple for baby/toddler/children’s clothing and for some this may actually be a stronger association than workwear. But remember, the first and last step to styling it so you don’t look like a toddler is to not literally be a toddler. But for more tips on that, see How to Look Older in Casual Clothes: Case studies with a graphic tee and a tulle skirt or my previous post on shortalls.
  • Head styling and shoes will do a lot to set the tone – that’s not any different from literally any other outfit (think the impossibly chic blogger in a t-shirt dress, but they have pink hair, trendy makeup, the season’s it-shoe, and tattoos, vs your random person in a t-shirt dress and grubby gym sneakers without all those extras), but I do find that these have a stronger effect with more “one and done” looks like dresses and jumpsuits.
  • Trends – A slouchy wider straight-leg silhouette (think late 90s/early y2k, rather than Greatest Hits of Pinterest) is more on-trend than a skinny fit if that is important for you, and IMO this better suits overalls anyway as they’re meant to go, well, over things. The classic relaxed-fit slightly tapered style I don’t think will ever look off, though. But I would foremost consider the types of shoes and outerwear you prefer to wear when choosing an overalls silhouette.

What to consider when choosing overalls

Fabric / Color

  • Soft or sturdy? – There are more options now than indestructible denim for fabric. Overalls are commonly made in denim, chino, and corduroy material, and even within these you can often find softer options at more fashion-oriented brands.
  • What seasons is it appropriate for? – Do you plan to style them more for cooler or mild weather outfits, or in summery looks?
  • What does the inside of the fabric look like? – A higher contrast on the inside will create a more noticeable cuff. This might be a feature you’re after, but I find that lower contrast cuffs are more versatile, especially if they’re going to be big fat chonky cuffs because you’re both short and too lazy to hem them (cough, me).
  • What aesthetics does it work with? – Is it a super clean looking fabric that suits a dressier or more modern vibe? Is it really ‘washed’ looking for a more casual vibe? Is the color easy to pair with your wardrobe? Does it have more of a workwear or casual wear feel? If you don’t want to look “too overalls”, choosing any other fabric than blue denim will do a LOT to shake that association and help them blend into different styles.

Utility / Fit

  • What strap adjustment mechanism does it use? – The traditional buckle, or does it rely on ties? Self-tie options can be more flexible, but they’ll also look more casual and if you’ve tied them really short you’ll have to deal with the extra strap length somehow or put up with them flapping around.
  • Does it have hip snaps/buttons? – If you have larger hips you will probably want these on the more fitted waist styles so you can get them on.
  • How many pockets does it have? – Don’t assume it has all the pockets if you’re not buying from a workwear brand. Check the description and photos.
  • Is the crotch meant to sit higher or lower? – More stylized silhouettes with a drop-crotch can be extra cool and comfy, but consider that you might have to deal with thigh chafe in those.
  • Skinny fit or loose fit? – How does this affect your shoe choices?
  • How wide is the bib? – Occasionally you see more fashion-oriented overalls with narrow bibs. Consider how this will interact with your bust.

Styling

These images were found via Pinterest, and the original pins can be found on this board. Please use common sense when following any links that aren’t to familiar websites.

The Classic and Not-so-classic Tee

First of all, there’s no requirement that you need to style overalls creatively! There are a ton of options layering them with just a t-shirt.

Bright colors, tie-dye, old camp/club tees and the like work easily for a summery casual look with sandals or sneakers.

For more relaxed styles, socks are always a good place to add another small shape into the outfit if you feel it needs more visual interest (vs something more superfluous like jewelry).

Stripe tees are another classic option that lend themselves to a more sophisticated casual styling with more mature accessories like below. Really the definition of ‘effortless chic’!

Changing up the silhouette of the tee alone can change up the outfit vibe. Oversized or drop-shoulder tees are great for creating a more easygoing feel. One great thing about overalls is that unlike with jeans, you won’t have to worry about how the heck you’ll tuck an oversized top! If you have a bunch of old oversized tees that are only worn as pajamas due to how annoying they are to style with jeans, overalls might give them another life as outfit clothes.

T-shirts don’t have to lean camp counselor or country. A trendy hat and athletic or skater style shoes can pull them more streetwear.

But again, one of the nice things about overalls is that you don’t need to do anything with them to get that bit of extra visual interest!

A trendy or unexpected shoe in monochrome is a good formula for a more fashion-oriented styling.

For a more alternative or artsy feel, you don’t even need any particularly interesting base layer or shoe if your head styling pulls that direction, since overalls also work in an artist/indie aesthetic (again, similar to jeans they were historically worn for physical jobs.)

But if you’re not into doing the whole hair and makeup thing, you can also easily get a more alternative or artsy feel if you use a nontraditional color or fabric of overall. The ones below are styled in a more matchy statement look, but they’d still feel creative-casual with a solid color tee.

Finding one with a print more strongly associated with a particular aesthetic can help blend them into your wardrobe. This look with a leopard print overall feels really glam when paired with shiny boots and larger earrings, even with a simple white tank.

It can be a bit unintuitive, but with garments like overalls, if it feels to you like you are wearing a garment that screams I AM WEARING OVERALLS, making the print as much of a statement as the garment type can lessen that feeling (although of course, only if you’re generally happy to wear loud outfits, and it was just the overall-ness that feels like it’s sticking out).

If you have a more traditional pair of overalls, you could DIY them into a more unique style with embroidery, patches, or fabric paint. Even if it’s not an all-over thing, I think adding a few motifs to say, the bib and one of the legs and a back pocket would be enough to pull them to a more artsy or cute aesthetic.

Layered up: Overalls for fall and winter

Anecdotally, I think for most people overalls are more of a warm seasons item since the quintessential pairing is with a short sleeve tee. But you can definitely style them for cooler weather as well!

The main thing to keep in mind if you intend to style overalls for winter is to get a pair in a fabric thick enough and loose enough that it doesn’t become awkwardly lumpy with the thickest base layer you intend to wear it with. Generally it will feel more natural if the top is not being squeezed by the overalls.

Fall/winter styling is a great opportunity to style non-denim overalls, like in corduroy.

If styling with a sweater, one thing I would pay attention to is whether you are creating more a seasonal mullet with the outfit than you want. Here the sweater is very thin and the overalls are a more tailored feminine silhouette, so it doesn’t feel confused when paired with a lower vamp shoe, versus if the sweater was chunkier or more wooly looking. Not my favorite outfit in the post, but it also doesn’t warrant any double-takes.

If you have a lot of neutral sweaters and want to add some color to your fall/winter looks, a colorful twill overall can be an easy layering option. IMO since overalls as a winter item are already more of an indie/creative feel, it might actually feel less like wearing a statement color item or at least less preppy than if you wore say, the coral pant version of the overalls below.

But you don’t have to style it as sweetly as the example above. A solid or traditional print crew neck sweater and boots work just as well for a more unisex styling.

With cardigans, I’d apply the same sensible layering rule of thumb: outer layers should be thicker and/or loose enough that it doesn’t feel logistically awkward or lumpy. So here the cardigan is loose fit and medium weight, but the overalls aren’t a super thick looking fabric so it works (plus there’s all the sweet print/texture in monocrhome going on). The outfit wouldn’t have the same ease if it was styled with say, one of those fitted 50s style cardigans.

If you don’t want to fuss so much about proportions looking conventionally flattering, I’d recommend pairing overalls with a longline cardigan like above with a more tapered overall. Since the overalls also go up pretty high (the horizontal edges in the outfit are smaller than if it was say, midrise pants), the outfit has a strong vertical flow.

For wide-leg overalls, if a longline cardigan just feels like there is too much fabric in the outfit, I think a substantial weight hip length cardigan looks really cute to break up the overalls area. If you have a hip length boxy cardigan that you feel makes too much of a half-half proportion when paired with jeans, styling it with overalls will bring things back to that less balanced vertical proportion that gets the eye to move more up/down the outfit instead of looking blocky. I really love this look Katie Holmes is wearing here! I think it’s a great demonstration of how a pair of overalls in a fun color can take an outfit that when styled with basic denim would be very ‘background’ to feel more cool/cute/creative without sacrificing the casual vibe.

Structured jackets can also definitely work with overalls. I think these are often styled in pinterest-blogger sorts of photos, but IMO pairing something like a moto jacket with a practical boot and using a more fashion oriented but structured bag to dress it up like below is a lot more wearable.

Going for a black/gray/neutral overall looks a little dressier/fashion-oriented than ‘had to run, was just gardening’ if the crunchier look isn’t your thing.

I think fleece jackets can also look really cute with overalls, especially for a more streetwear look when paired with sneakers instead of boots. This could also be more comfortable than a more structured option as a sweater or sweatshirt with the overalls bib can get chunky.

How cute is this? More of a retro look with the bright crew socks and dad sneakers. This styling is definitely more on the statement side, but I can see the same formula working well with lower profile New Balances and a longer, less highwater crop to the overalls.

I couldn’t find many photos with other types of jackets, but I think the “shacket” style and quilted jackets that are trendy now both could work well with an overall as they work with the whole casual+structured thing.

For shackets or flannels, going for a less conventional print or color can make it feel less farmer if you are trying to stay away from that. But again, head styling and boots does a lot. In the outfit below, the head styling is definitely more on the polished side, and the boots are pretty sleek so at least to me it definitely has more of that street style candid vibe! Again, like with the moto jackets, the bag also does a lot to set the tone of the look.

For pairing with longer overcoats, IMO traditional blue overalls will need a LOT of styling thought to feel intentional with a more formal tailored wool sort of coat. I personally don’t think the outfit below hits the level of cohesiveness that takes it to ‘creative fashion’ over ‘it was laundry day’. Usually I find that if the peripherals all match (such as the coat, clutch, and pumps here) it’ll be plenty cohesive that whatever underneath can work (for example, you often see blogger photos with matching sweats sets under a fancy coat with a formal bag), but IMO the wash, cuffs, and distressing on the overall is just too jarringly casual against everything else. If I was going to style this, I think going with a pristine white sneaker would tie the elements together better, as that can go with the ‘city polished casual’ vibe of the solid coat and classic button down while making the overalls feel less orphaned.

I really liked this outfit with a longer coat. The loose trench both looks more like it would actually fit over the base outfit comfortably and since trench coats have a less formal background than tailored wool coats (as they’re always touted as one of those dress-up dress-down pieces), it’s an easier pairing with the overalls. I also think that the overalls being more of a single color creates a cleaner feel that dresses up better.

I think this is more of a coatigan situation, but the winter whites are really chic and I like how the overalls make it less of a fussy look than it could be with a blouse and slacks. Again, IMO non-blue overalls will be easier to style in less traditionally-overall-y ways.

Dressed up: overalls with button downs and blouses

Anyone who claims that overalls cannot look sharp has clearly never seen the below outfit. All the pieces are very visually clean and look perfectly tailored, and the boot has a lot of fashion oomph. Not as editorial, but you could definitely get a similar feel with any sleek pointed toe boot even without a four inch heel.

Overalls with shirts or blouses don’t have to feel dressy, though! A short sleeve button down can make the outfit less crunchy without going too dressy, especially when paired with a practical shoe.

Rolling the sleeves of a long sleeve option can also dress it down to vibe with a pair of overalls.

Menswear inspired shoes like oxfords and loafers can work when the top is a more dressy style. It’ll keep that grounded feel despite being more formal, and they’re also usually a little more substantial looking than ballet flats, which I think could easily be overpowered just by the visual weight of overalls. I generally like the styling of the outfit below, although I suspect it was taken during the height of cropped pants everything, as currently I would say that would look sleeker with a more traditional length on the pant.

Another example of an easy-peasy short sleeve button down look, with clogs for a more artsy vibe. If you want to go the more casual route with button downs, I’d look for something with a camp collar shirt instead of the type meant to button all the way.

I am very excited for the possibilities of an overall with all the statement collars that are in now. I think that’s a great way to add a feminine touch to the outfit without going too delicate. Personally I would 100% wear the outfit below! Casual and a little whimsical. Generally though I’d go for collars either with a higher closure like below, or a neckline that is drapey enough that it won’t look awkward if it gets squished a bit by the overalls. The collar should work with the overall bib, not fight it.

Look how darling this is! As someone who often feels too “office-y” or just preppy with trouser + blouse outfits, I am really digging how the more whimsical colors and prints of overall work with romatnic blouses. This small scale polka dot really ties in with any white top, and this also looks like something that could be DIYd with fabric paint (although tbh it does look like it would be a project for someone with a lot of focus!).

Here’s a styling that I feel works with flats. The top is very feminine and the overalls are a more skinny cut, so it flows more naturally into the shoe. I think it also helps that it’s a nude tone flat, as it doesn’t additionally break up the rhythm of the edge of outfit. With the cuffed pant, I think a contrasting color flat might have looked too busy.

Blouses and colorful overalls doesn’t mean you have to look fussy or go for a tailored fit. This is a fun more-is-more look with big sleeves and a bold print! The monochrome and lightly styled headstyling create a more ‘for fashion’ effect than laundry day effect.

A more low-profile blouse without a stand up collar or statement sleeves is also a good way to bring a look away from the ‘was just gardening’ feel without getting too formal but also not leaning into streetwear.

Extra relaxed / no waistband

For a statement but not formal overall option, you can try an extra oversized silhouette without a defined waist seam. I think this lends itself to a more mori-kei or lagenlook aesthetic.

For a bit more definition, you can look for a style that can be worn cuffed.

Again, the shoes and base layer play just as big a role as the overall in setting the outfit feel. The first look in this section is very gardencore, the second with the strappy sandals and more glam makeup feels more fashion-oriented, and the look below with oxfords and no sock feels a bit smarter and more structured without feeling slick or stompy.

Vintage Style Jumpsuit-Adjacent

I would consider the styles in this section more of a plunge jumpsuit than an overall, but if you like the instant visual interest of layering overalls but prefer a more polished or feminine look, these are a good option! I’ve seen these labeled as both jumpsuits and overalls at various stores.

They’re especially suited to more 60s/70s vintage styles!

When shopping for these, pay attention to the closure style since they’re quite tailored at the waist.

How I style overalls

Here are a few recent overalls looks I’ve put together as I’ve been buzzing about this post.

For a full length option, I was really pleased with the Free People Ziggy Railroad stripe overall in a L. I got green/black stripe, because I felt I’d be more comfortable with a less traditional color plus the green goes well with the neutrals and earth tones I have.

Worn above with a Target botanical illustration graphic tee and Birkenstocks. Below the same outfit with a hip length raglan sleeve cable knit cardigan (also from Target, in a size L).

One of my fall/winter staples is these gigot lace-up sleeve waffle knit tees (Free People Tasha thermal, M), so I was pleased that the overalls worked with them! I like how the top adds a romantic touch while still being casual/washed out looking to not actually feel dressy. I have to make quite a large cuff for these to fit (haven’t hemmed them yet), but I don’t mind how it looks with my similarlyy chunky platform Dr Martens Leona boots. This is a good style of overall for me if it works with tees, chunky granola style sandals, and my winter basics!

After I took that day’s outfit pic, I remembered that I recently bought some vintage pins on eBay and figured they could work on the denim bib. I liked the whimsical touch they added! I want to mix them with more modern enamel pins once I have collected a few.

Also tried styling them with a ruffle eyelet blouse (Maeve via Poshmark) and my platform clogs for a dressy-folksy look. I didn’t get a photo, but I don’t like the shoe/cuff pairing when wearing these with lower profile shoes like my derby flats. When the cuff is the size of the shoe, that’s just not it for me.

A shortalls outfit I wore since the shortalls post, embracing the basic fall vibes with a flannel (Madewell Sunday Shirt in “Emmy Plaid”, S via resale), messy bun, and black chunky boots. I really enjoyed this one, I felt like I should be visiting a corn maze or something.

And just for reference, here are two shortalls looks I’ve shared previously, because I really like them and think they’re worth resharing 🙂

An extra lok and a more muted styling, ft the same base. (Handmade cardigan via Poshmark)

Shoulder bag is the Madewell Oversized Shopper, cardigan is secondhand BDG (Urban Outfitters)

Where to Buy Overalls

If you are as hype about the possibilities of overalls as I am and want to pick up a pair, here are some brands you can consider. Again, this is for reference as a starting point, and the styling options discussed in the previous section were more to get your brain going on how you might be able to integrate a pair of overalls with the stuff that you might already wear a lot, or have been wanting to wear but have left in your closet because it doesn’t go with any of your bottoms. Don’t feel like you need to buy a second wardrobe just to wear overalls! And of course, you can also use this guide to help filter down when searching resale.

Size inclusive

Lucy & Yak – lots and lots of colors and patterns

Copper Union (size 12 and up) – Drapier fabrics

Target (the Universal Thread line, in particular)

Old Navy (they also have a maternity selection)

Hard-wearing

Overalls from brands that are meant for actual work, and look as such. Although there are some more for casual wear or in fun colors here too! Duluth even makes a pinafore dress.

Dickies

Carhartt

Duluth Trading Co

Feminine / Vintage Aesthetic

Anthropologie

Unique Vintage (NB: not literally vintage, or unique)

Modcloth

Free People

And of course, there are also Levi’s. Although currently they seem to stock much fewer overalls than I’d expect.

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