Happy Tuesday! I’ve got not one, but THREE outfits for you today — all centered around overalls. Been curious how to wear ’em in the fall? Keep reading for three outfit formulas.
LOOK ONE / Overalls with a chunky sweater
I have to admit, I was skeptical of wearing something “chunky” underneath overalls. Will it be too bulky? Will the sweater spill out on the sides and look weird?
Well, yes the sweater will spill out.
But no, it doesn’t look weird.
It looks pretty cool and slouchy.
However! Watch out for weird bumps when you’re tucking your sweater into your overalls. My strategy was to tuck the front and back first so I could get them nice and flat, then I bunched up the sides and tucked them second. Leaving the sweater bunchy at the sides gives the whole look a slouchy and relaxed vibe.
Here’s a few more outfits with this sweater, in case you’re wondering what it looks like untucked.
01 | Sweater (old by Forever21) | similar by Urban Outfitters | similar in an oatmeal color by J.Crew | similar by Everlane (made responsibly)
02 | Overalls by Madewell (just a few left) | similar by Madewell | similar for less
03 | Beanie by Iron and Resin (made in USA)
04 | Ankle booties (old by Sam Edelman) | similar by Madewell | similar by Fortress of Inca (made responsibly)
05 | Bag gifted by ONA | similar (made responsibly) | similar (made responsibly)
• • •
LOOK TWO / Overalls with a button down flannel shirt
Turns out I was skeptical of look two, also. I was nervous that a plaid shirt + overalls might read too country for my style.
But it surprised me.
Yes, it’s casual, but paired with the cognac ankle booties and tote, it feels right to me. In fact, I think it’s my favorite look out of the whole trio.
It’s the kind of thing I’d wear to hang out with my family and play with my nieces and nephews. It’s super casual and wearable, while still being a little playful and cheery.
01 | Plaid shirt (old by Madewell) |same shirt in a navy + burgundy color scheme by Madewell | similar by Anthropologie
02 |Overalls by Madewell (just a few left) | similar by Madewell | similar for less
03 | Ankle booties (old by Sam Edelman) | similar by Madewell | similar by Fortress of Inca (made responsibly)
04 | Bag gifted by ONA | similar (made responsibly) | similar (made responsibly)
LOOK THREE / Overalls with a long cardigan
This was one look I was not skeptical about at all. I knew I’d love it before I even tried it out.
In case you can’t see it, I’m wearing my stretchy long sleeve base layer underneath. It’s super fitted, so it fits underneath the cardigan nicely while still giving me two long sleeve layers. And then I wrapped it all up + added warmth with my cozy scarf.
So, real talk. If you have overalls, but haven’t worn them yet because you feel like they are too much of a statement, try styling them like this. The long cardigan and scarf almost disguise the fact that you’re wearing overalls — giving you time to wear them all over town and get used to them with a nice little safety net. Yay!
02 | Cardigan by Halogen (back in stock!) | similar | similar under $70 in a wool blend for colder days
03 |Overalls by Madewell (just a few left) | similar by Madewell | similar for less
04 | Scarf by Free People
05 | Ankle booties (old by Sam Edelman) | similar by Madewell | similar by Fortress of Inca (made responsibly)
So tell me, which look is your favorite? Got any other fun ideas for styling overalls in the fall? And … if I did another one piece, three ways post, what item would you like to see featured?
The overalls I have are more of a loose boyfriend style so I’m unsure if they would work styled these same ways. Thoughts?
Hey Cara, I would say to just give it a try! I’ve seen them styled in a lot of cute ways. I think it’ll work, but it ultimately comes down to what you feel comfortable with. :)
Barbie Beauty says
Love the second style need less to say plaid goes with anything, you look great too
Thank you for featuring your overalls in this great post, Caroline! I purchased these same overalls after you featured them over the summer, but I’ve been too nervous and self conscious to wear them! I plan to break them out this weekend with a long cardigan. Like you said, it is a great way to ease into the style! And anyway, if I like them, who cares what anyone else thinks!
Bonnie Rae says
I needed this! I haven’t been wearing my Madewell overalls because I didn’t know what to pair them with, thank you :)
Great ideas! Love them all. Can’t wait to wear mine with a sweater here in CA :)
Could you please share the size of your Madewell flannel shirt? How does it fit? Thank you!
Hey Jaime! The plaid is an XS, but if I were getting one now, I’d probably get a S or M for a more oversized fit. I’d say it’s true to size though, so it just depends on the look you’re going for. :)
Those overalls fit you like a glove! Like, I’m super impressed. I think it’s neat that they are reinvented as a more flattering silhouette. The ones I remember from the nineties were baggy baggy baggy.
I absolutely loved that sweater underneath. What a unique and fun pairing.
Hey Laura, I agree. I think the fitted silhouette helps it feel more… modern? I know I’m more comfortable in this fit than I would be in baggy overalls. :)
i personally don’t care for overalls but those look great on you. :) ox
Marie Therese says
I totally go see myself wearing the second outfit. I feel like the slouchy sweater would drive me crazy ; p
And I finally figured out who I think you resemble: Feist! Have you gotten that before? :)
Marie, I haven’t heard that before about Feist, but what a high compliment! Thanks! :)
Tanya E says
Oh, I like all 3 ways! I haven’t bought overalls (dungarees,here in the UK) but I need some more dark jeans, so I might expand my search. I really like your fitted style dungarees, they look more put together, somehow.
I love outfits 2 and 3, but they all look good. The plaid gives off a very cool vibe. I would love ideas on how to wear a jumpsuit in the fall/winter. I only wear mine in warmer weather.
Logan Smith says
Love this! I actually just got a pair of overalls in the mail yesterday and was worried I wouldn’t know what to pair them with, so I am so excited for this post! Have you tried pairing other shoes that work with them besides booties?
Hey Logan, I paired them with my clogs here: http://bit.ly/2fTfTG4 and I think you could probably wear them with anything that you wear jeans with — sneakers, sandals, a chunky heel, etc. What were you thinking of trying? :)
I love these outfits, Caroline — Especially the first one! Overalls are so cute in the fall time! And thanks for all the little tips!
Caroline, these overalls REALLY suit you. The first outfit looks like you’ve stepped out of a cool girl catalogue. The second is just really cosy and third has such a casual chic vibe. I think the first is my favourite. Also I love the warm tones – they really take it to the next level.
I feel like to pull overalls off you have to have a certain body shape, which I don’t so I steer clear for now. And baggy overalls on a non-model body look like you’re trying to cover up a pregnancy or like you’re about to go paint your flat (they always wore them for painting in the 90s movies).
If I did have overalls though, I’d also try to style them with a boho embroidered blouse and also maybe a shirt and sneakers. (Not white shirt and heels because that’s just a big basic I think)
The only thing I can think of I’d like to see styled in 3 ways are the mom jeans. I just love them on you!
Have a great day,
I have these same overalls and I get compliments on them all the time :-) I like to wear mine with a thinner turtle neck and a cardigan over top. My only complaint is the cropped length–my ankles get cold!! But to remedy this I wear them with my cognac combat boots and some chunky socks.
That sounds really cute Camille! Thanks for sharing :)
These are such fun looks Caroline! I’ve never tried wearing overalls, at least not since I was a kid in the 90s! Maybe I’ll give them a shot some time!
Lauren, I hope you do! They are pretty fun :)
Anna Kay says
Do you ever feel like you don’t “look right” to pull off a style? I have curly hair & freckles, and as much as I love these looks, I have a deep-seated fear of coming off too Laura Ingles-Wilder! Just wearing plaid (a personal favorite) can be a struggle… Do you just dismiss it and love what you love?
Hey Anna! That’s definitely a struggle. I try not to get too hung up on my insecurities, but I also know I won’t love the outfit if I feel too far out of my comfort zone. It’s really just a step toward finding that personal style, though. Trying things out and seeing how it goes. I didn’t even think I would love the first 2 looks in this post, and I did! So you never know. GIve it a shot and you might be surprised… :)
Laura Blanton says
I love all of these looks but find myself wearing the heck out of look one! And I’ve gotta say I have yet to try the long cardigan over them… so I guess I’ll be trying that one soon! ;) I think the only layering piece that doesn’t feel right with them is, oddly enough, a jacket. Would love to know if you feel the same way.
Hey Laura, I’ll try to work on some looks with overalls with a jacket! :)
I love your blog A LOT LOT LOT! Also this post: you look so happy in your clothes. I’m trying to have back that feeling, and your blogs are helping me a lot. Thanks, thanks, thanks!!
My overalls are black and sometimes I feel like they come across really intense and in your face. Thoughts on black overalls? Do they seem more dressy or less? Going to try these formulas this morning!
Hey Shea! I don’t think the color would matter as much as the fabric. If they are denim, maybe try pairing them with something you’d normally wear black jeans with? I’d probably also scour Pinterest a bit to nail down the vibe I’m hoping to give off and go from there. Good luck! :)
This post came at the perfect time! I’m nine weeks pregnant and I love my high waisted jeans but they aren’t really conducive for my growing belly. I have a pair of overalls and just totally forgot/didn’t realize I could wear them in winter.
I just did the sweater and overalls and absolutely LOVED it! I was able to pair with a sweater that I have kind of grown out of in terms of style because it was always too blah by itself. Thanks for the great ideas!
Hi Caroline! I’m a first-time commenter, and I have to laugh that it’s on a post about overalls (I did them in college and vow never to return–but they look cute on you!). Anyway, I need you to know that I’m finding myself turning to blogs–design, fashion, etc–even more in the past week as solace in this post-election. So please don’t question the fashion (and mindfulness) posts, because our country, liberals and conservatives alike, need a distraction right now.
Caroline parish says
Loving your style; you look so elegant in your dungarees! I would look kind of dumpy I fear, so havn’t got into them. I do however have a dungaree style denim dress (fat face) ; would you style it in a similar way do you think? I wear a lot of dresses as they suit my shape. Could you show a sleeveless pinafore dress styled 3 ways, pretty please??
Obsessed! Overalls are such a style staple for me. I love the flannel pairing!
I’m impressed how you’ve updated overalls to look modern and appropriate. I’d consider a pair if I found ones that fit as well as these fit you.
Stunning and inspirational ways on how to style overalls! I was always thinking on how to style mine. Going to try out and combine a jumper with it too. :)
Love the ways you styled the overall!
Liesbeth Verlinden says
Damn you, caroline, I was considering overalls and with this post now I just cannot stop thinking about it! Hoped it would pass because it seems like too much of a whimsical purchase and I can’t find a sustainable, second-hand or (final option) cheap highstreet model where I live. I’ll just have to mull it over a little longer…
Anna Oates says
Love the cardigan over them! I don’t see that too much but I really like the way it looks. Then again I love about anything with a cardigan. I have been thinking about buying a pair. If I still feel the same next season I might bite the bullet!
Great ways to wear overalls ! I tend to just add a tshirt or a light coloured button down.
I have to try the turtleneck option as I think is looks fabulous.
Hi Caroline! I know these overalls are sold out, but would you mind sharing the style name and color? They are soooo cute! Hoping to find them on Posh or eBay (none of the links work anymore to check them). Thank you! – Maresa
Hey Maresa! These are called the skinny overalls in Camilia wash. Good luck on the hunt! :)
I was wondering what size you took in the Madewell overalls?