Style Notes: Short Overalls

How to style shortalls so you don’t look like a toddler

  1. Don’t literally be a toddler

๐Ÿ˜„ That covers it, but in case you want to go the extra mile, here are some notes on outfits I’ve styled with a new pair of short overalls that I think spans a decent range of playful and cute and sophisticated and crunchy.

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The Shorteralls

I did a poll on Instagram, and it seems like “short overalls” is by far the most common way people refer to this sort of garment. Although, to be fair most of my audience is in the US, so “dungarees” and “jumper” did not get nearly as much traction. “Shortall / shorterall” was the second most common, and the one that I personally use, solely because I am a sucker for a good portmanteau!

Anyway, the “Werk & Play Denim Shortalls” from Aerie are a new item, and as of writing is in stock in XXS-XXL in all four colorways. I typically order a M in tops and L in bottoms at Aerie (I currently usually wear size US10-12), so I got this in a size L and it fit great! I got it in “Rebellious Mauve” because the purplish brown color was unusual and felt like a good ‘non color color’ or ‘colorful neutral’ or whatever term you have in your head for colors like muted olive, maroon, navy. I do have a lot of true neutrals and orange/green in my wardrobe, so purple seemed like it would fit in!

As a relaxed-fit style, these are not going to be creating a va va voom hourglass figure. But the upside of these not having a waistband, is they don’t have a waistband. Holy moly, these are so comfortable and I cannot believe that I’ve completely eschewed this entire class of garment until now. It’s like a sack dress, but with the structural integrity to support five giant pockets. I also ordered the twill overalls in a large, but I found those much less comfortable than the shortalls because as I moved my legs around, they pull on the rest of the garment a lot more. It wasn’t exactly uncomfortable, but it definitely didn’t feel as freeing as these.

If you’re looking for casual shorts and are over finding the right fit of a non-stretch option in both the waist and hips, but don’t like a loungey look that elastic band shorts often have, I would seriously consider trying shortalls. Still casual for sure, but more of a gardening or art studio vibe than lounge.

As for fabric, are a thin and slightly stretchy denim, so it’s lightweight and quite comfortable. It isn’t so light that it feels insubstantial, but these are likely not going to reach handmedown status if worn regularly, because it’s not a super sturdy work quality denim. All pockets are roomy and the snaps seem pretty sturdy.

I like that I can adjust it such that the inseam hits where I can walk without thigh chafe, but I haven’t worn these in truly hot weather yet so not sure how it’ll do on that end in sweatier conditions.

There’s a really cute subtle floral embroidery on one of the back pockets too! I think this is unique to the mauve ๐Ÿ‘€

I haven’t previously been drawn to overalls or shortalls in the past, as they seemed too bulky to be versatile and the blue denim ones always felt a little too basic-pinterest/tumblr or farm style for what I was going for. Also, inspiration photos that came up and styling examples in stock photos are super repetitive.

But as I’ve both come back around to wearing more casual styles (in the flavor of ‘crunchy casual’ โ€“ hippie but think camp counselor instead of stoner yogi) and have discovered the wonders of layering pinafore dresses, they looked like an intriguing option to spice up layering options in that realm. Plus, with the right styling I think they could also work for cottagecore or storybook style, with the gardening connotations and all.

For full excruciating detail on how to look older in casual clothes, see the blog post. But the TL;DR is:

Ask yourself, “would you literally dress a five year old in this?” and then add or swap out pieces until the answer is “no”.

I am aware that they make Dr Martens for toddlers and that you can find all sorts of extravagant child sized party looks, but the idea is that incorporating items that can be described as at least one of

  • structured
  • delicate
  • edgy
  • luxe

will generally pull the outfit away from the softer childlike look.

Additionally, generally making sure the accessories or outfit color scheme feel cohesive will create more of an intentional feel to the outfit even if it’s more on the playful side. Like, the stuff you see on @tokyofashion doesn’t usually give a childrens clothes vibe, even though it can be just as extra as a 3 year old who wears their favorite sequined tutu every day regardless of base outfit.

I find that accessorizing, even with just one item, or just choosing a bag that complements the outfit a little better is often enough to make a look feel intentional, simply because it is. Like, the bare minimum you’d need to throw on to get out the door here is a top + shortalls + shoes + maybe a bag, but if you take the time to add a hair accessory, watch, hat, or jewelry then that signals your outfit did not happen on accident.


The usual disclaimer that this is all meant as inspiration in case it tickles your fancy or you have similar items already. It’s not a prescriptive “you must only use neutral shoes” or whatever. There are lots of other ways to style overalls, this is just how I make them feel like me!

1 โ€“ To me, any outfit with a straw hat and Birkenstocks is a farmers market outfit. I can count on one hand the number of times I’ve gone to a farmers market, but if I were to go again I could definitely wear this (with foldable grocery tote in purse, of course)

The hat and crossbody are both structured items, and the neutral palette also creates more of a mature vibe.

Sand Diego Hat Company hat // Anthropologie purse // Birkenstock Arizonas in mocha birkibuc

1.5 โ€“ Despite being a blogger favorite for their picnic vibes and visual interest, wide-brimmed hats are often not practical even outdoors due to wind, and you probably aren’t gonna keep it on inside your home. But swapping it out for a satin scarf-style headband in a muted green still looks pretty put-together, and keeps the accessorized look of the outfit going.

Anthropologie headband

2 โ€“ A very ‘community garden’ sort of vibe, with a dash of 90s throwback. With the velcro sandals and hair bandana, this outfit is one of the more causal and youthful leaning ones, but even a detail like swapping a backpack for a good quality canvas tote brings the aesthetic more towards gardening instead of field trip.

Madewell bandana // Trader Joe’s tote // Tevas sandals

3 โ€“ Combat boots and slightly quirky styled hair IMO will always add an intentional vibe to any outfit. No matter how boring or weird the base items are, hair doesn’t just do that by itself, and one does not simply stumble into lace-up platform boots.

Of course, if your goal for your wardrobe is to own items that will make you look put-together without actual extra effort, you’d probably curate a much tighter aesthetic in the clothing items. But in this bunch of outfits, I’ve generally gone more eclectic with the colors, so without the benefit of more intrinsically sophisticated-mature-chic-whatever pieces (think @jeanwang or @gemary), to feel like I’m doing maximalism on purpose rather than because I have lost my handle on my closet, I want to pay extra effort into head styling and shoes.

Handmade cardigan via Poshmark // Dr Martens Leona boots (discontinued colorway)

To elaborate on the omnipresent “add a third piece” advice, for outer layers here, I’d stick to looser and heavier items like this oversized sweater. Since overalls are relatively structured and loose fit, they can look lumpy if you pair it with something more fitted or thin.

Pieces that hit pretty close to the shorts hem also generally look less chaotic than ones that hit at the hip or waist, since there’s already an unusual cutoff line created by the top of the overall. So here even though there are three fairly loud layers, the vertical lines in the outfit dominate.

3.5 โ€“ Added scrunchies. Cause everything else is so loud, this feels more visually balanced, but also more costumey. Not sure if Pokemon bug catcher or Animal Crossing villager. But I dig both those aesthetics.

4 โ€“ Cozy grunge? I think this is one of my favorites in the batch. It’s such a calming blend of whimsical and muted. Again, while on this cardigan the sleeves are more snug at the ends, the overall fit is still looser and boxy with a chunky yarn, so it’s not too clingy.

Madewell bag // Urban Outfitters cardigan via Poshmark // Dr Martens boots

5 โ€“ I tend to use blue denim and chambray sparingly, but with the mauve color of shorterall, this chambray shirt is a great “colorful neutral” to brighten up the look, and helps bridge the more normcore New Balance sneakers with the fancier bag.

Vintage Jurassic Park patch shirt via eBay // Madewell Tote // New Balance Classics

6 โ€“ More whimsical silhouettes can be toned down by doing them in neutrals, particularly black. Personally, I like mixing black + white for this (in this case it works particularly well since the boots have a black chunky sole) to keep things from feeling like the matching black or white is a more statement part of the outfit (if I’m not going for that โ€“ I do love a good witchy look ๐Ÿ”ฎ).

Free People Tasha thermal top // Dr Martens Leona boots (discontinued colorway)

7 โ€“ Still, part of the fun of overalls is capturing some of that childhood nostalgia, so I’m actually not opposed to styling it with a bright 90s tee and sneakers. But it’s nice to change up the styling of overalls when I feel like it.

Vintage tee via eBay // New Balance sneakers

Do you have overalls or shortalls? What’s your favorite way to style them?


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