188 Comments
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Grace Atwood's avatar

Kelly, This is a goldmine, thank you!

Also, thank you for including a range of body types. Sometimes I can feel like the key to pulling off an oversized button-down (or oversized clothing in general!) is to be rail thin. This was refreshing! x

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Kelly Williams's avatar

Yes! Thank YOU for noticing, it’s a major goal of mine. I am short and often feel frustrated because images are always shown on tall (and, as you said, skinny!!) women. I’m so glad you liked this!

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Cathy 🇨🇦's avatar

Yes! I had the same thought as Grace this was really helpful for visualizing.

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Lindsey Johnstone's avatar

Amen!

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Sarah | Fewer & Better's avatar

Oh I have the ultimate tip for this!!! Choose a men's shirt one size up from your usual size. Instant chic, perfect oversized fit, hits the right length, etc. I stole my husband's for my Three Recent Outfits post last week and, if I do say so myself, it is excellent. I wore it tucked in but I also wear it loose!

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Kelly Williams's avatar

PERFECT ADVICE!! Thank you Sarah! I love shopping men’s but struggle with sizing. Now I know to go one up. I don’t think men’s retailers mess around with oversized/fitted so their fits are more standardized!

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Sarah | Fewer & Better's avatar

Yes which is SUCH a relief, because I know I can go into Brooks Brothers or Sid Mashburn and get the exact right fit for me without trying it on! (Plus, better quality than most women's shirts, let's be real.)

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Kelly Williams's avatar

PS what’s up with men’s clothing being so high quality and that not translating to women (some times)?!

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Brit Southworth's avatar

Men don't trend shop the way women do so companies, even JCrew, gap, etc put more money into quality. You don't need to make quality sweaters for women if they are just going to get a new one next year. I don't remember where I learned this but I've found it to be true. It's why I shop the mens side so much.

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Kelly Williams's avatar

It's so true. Even as I was writing it I thought; "men's are better quality because they wear one sweater for 15 years." Anyways, I'm officially changing my entire shopping habit starting now.

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Sarah | Fewer & Better's avatar

I have literally no idea!! My husband's sweaters don't even pill!

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Brit Southworth's avatar

This. I lived in my mens JCrew linen button downs last year.

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Meighan Grady's avatar

These are also ALWAYS on the men's sale rack at J.Crew in fun colors/stripes. I got a great green one last year for like $10. Fab hack.

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Sogole Kane's avatar

I literally had to wait until I had time to come to my ACTUAL laptop to type my comment bc I HAVE SO MUCH TO SAY!

This post was genius (not surprising). I've actually been toying with the idea of doing a post all about a combo that I am dying to embrace but somewhat shy to thanks to my elder millennial training...that of the giant oversized UNTUCKED button down shirt with a slimmer pair of pants, (Feeding a bit into Tibi BSS) I think it's so fresh and if I could just get over myself...I may pull it together.

But I digress! First off, I LOVE THE DIAGONAL TUCK and I've been doing it for at least year now - I think TikTok introduced me to it. SPEAKING OF TIKTOK--I haveeeeee to share this post that literally changed my button down game: https://www.tiktok.com/t/ZP86jvjGK/ - it's just too good!

SO MANY great styling ideas and overall insights. I find that a crisp poplin always does the trick for me, but I love Oxford and silk, too, for different functions. FINALLY I will ALWAYS call it a button-down, no matter how wrong I am...bc you BUTTON IT DOWN from the top to bottom. I'm sticking to my logic :) xoxox

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Kelly Williams's avatar

Sogole!! That TikTok! I’m trying it immediately because that button trick is gold; like my mind is blown 🤯 please, please do a post on the untucked oversized shirt because all the celebs I mentioned are wearing their button up that way but I struggle to do it myself. I need all your tips!!

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Sogole Kane's avatar

Isn’t is so genius?! I’ll work on said post— it’s a bit out of my comfort zone but I’m obsessed with the idea of this formula - you’ve started a great convo!!

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Stephanie Smith's avatar

If you just have the tailor put one button to the side( or 2,3 a La Lemaire), it’s easy good luck ♥️. I know it sounds complicated but if you go into the mirror and unbutton your shirt you can see where is most flattering. Lower left side for a woman. Also Kelly you are adorable 🥰

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Kelly Williams's avatar

💁‍♀️ THANK YOU! Also, I don’t know why I haven’t thought of just having my tailor add a button; I’m practically best friends with my current tailor so he could certainly hook me up!

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Stephanie Smith's avatar

I love that your bffs with your tailor!!!!!

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Stephanie Smith's avatar

Me too Sogole always a button down lol

♥️

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Angharad Jones's avatar

LOVE. I live in my oversized shirts (especially in spring/summer), and I concur with all of this advice! I tend to size up (only one or two sizes if the fit is already relaxed). I also like the look of buttoning the cuff, turning it up one and then pushing the sleeves up to a 3/4 length (can hold in place with an elastic if it's not staying up) as an alternative to rolling the sleeves up. It creates a nice bit of volume too.

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Kelly Williams's avatar

Angharad! I tried this roll and push technique this morning and I LOVED the volume it left in the arm. I need to use an elastic to get it to stay but it’s a brilliant tip.

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Angharad Jones's avatar

Yep, it normally needs a little help to stay in place but it's so worth it!

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Kelly Williams's avatar

You look DREAMY in button up shirts so I’ll do whatever you say.

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Angharad Jones's avatar

😂

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Jennifer Klee's avatar

SUCH GOOD INTEL. Gen Z and their crazy rules are so comical to me. I am going to be sporting a French tuck as I cruse right into an Assisted Living facility and nobody can stop me. There is an Ann Taylor option (Search: "Weekend Collection Oversized Shirt"- the link was too ugly to paste here) that has been a very good purchase. It's nice and medium thickness, and I believe it will wear in very nicely. Note the covered placket which may or may not be a desired feature.

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Kelly Williams's avatar

Gen Z trying to wipe the internet of our amazing fashions; how dare they?! Just searched for the Ann Taylor shirt bc I like a covered placket (sometimes) AND I’m intrigued by the cropped option.

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Jennifer Klee's avatar

GenZ is my own children, and thus I feel completely empowered to tell them how wrong they are. My Ann Taylor (really outing myself as older "wiser" here, whatever!) is not cropped, it's just solid blue wonderfulness.

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Kelly Williams's avatar

I think my children are called Generation Alpha and I’m already terrified for what they will do to me.

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Monica Lee Rich's avatar

This was fun. I recently grabbed 2 men’s Jcrew poplin secret was “button downs” off EBay. I had been wearing a version of my sons cast off to paint in the studio. I loved to weight of the cotton so I decided to pick up another one, then another one AND, I’ll add, men’s shirts often have an extra button on the forearm which helps keep the sleeve in the perfect spot when you push it up.

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Kelly Williams's avatar

BRILLIANT!! How did I not know about that sneaky extra button. I’m in a deep rabbit hole of Baird McNutt JCrew button downs on Posh and I need to just buy already.

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Dewie's avatar

Hello Lovely Friends & Shoppers

I cannot believe out of all these comments the word boobs appears just once. I have avoided button downs (not sure who has naming rights to shirts but they have been button downs all my life from coast to coast and country to country.) Back to boobs, anybody have advice on button placement if you dont want to go so oversized you look like you are in a trimester but almost fits the buttons always gap ? Many thanks to Kelly for keeping me from working ;c)

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Kelly Williams's avatar

Ha!! I love this comment so much! Ask about the boobs. I am mid to small chest size so my advice is limited. I wonder if the Midimalist chat as thoughts too 🤔

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Kelly Williams's avatar

Ha!! I love this comment so much! Ask about the boobs. I am mid to small chest size so my advice is limited. I wonder if the Midimalist chat as thoughts too 🤔

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Anne's avatar

Currently 34J bra size and I mostly wear button downs over a fitted tank/cami and do not button them over my chest. I have noticed that I can get away with a shirt that’s big enough to close over my chest if I tuck or half tuck it into something high waisted - avoids the dreaded pregnant/tent look!

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MO's avatar

Has anyone tried WNU shirts? I keep hearing they are the best but stumped on style, material, sizing!

Separately, this was incredibly helpful-- thank you!!

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Kelly Williams's avatar

Yes!! Find Alyson’s comment because she was saying she owns them in two different materials and/or styles! She’s got the intel.

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OFELIA's avatar

Angharad owns a few I believe!

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Brit Southworth's avatar

This was fun. And the only way I can wear a button up is easeful and slouchy. Otherwise I feel like my mother (no offense, mom). Looking for the perfect slouchy denim and chambray options if anyone has recs.

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Kelly Williams's avatar

I second this ask!! I have a chambray that’s 10+ years old that I love but it’s more fitted than I want. This is a top contender but I’d love boots on the ground about it! https://www.aritzia.com/us/en/product/the-'80s-comfy-denim-shirt/114191007.html?color=29866

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Brit Southworth's avatar

I have been eyeing the aritzia one also. Ralph Lauren makes an oversized one that is good too.

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Kelly Williams's avatar

Ooh Sarah this is checking all my boxes! I have another AYR that I love the drape on. Thank you for this!!

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Brit Southworth's avatar

I have always liked the look of the deep end. But the sleeves look short. Would you say they are full length or more like bracelet length. Also did you size up?

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Veronica Bryant Bean's avatar

This is the first Substack I’ve ever saved! Thank you for doing the lord’s work!

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Kelly Williams's avatar

Veronica I am HONORED!! I am chuffed that you liked it.

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Priscila Smith's avatar

Button ups are a huge part of my everyday style. The AYR makes such great ones that feel worn in. Next up one favorites are the Gap organic ones! But truly my love lives in the worn in men’s Ralph Lauren shirts I find at thrift stores and add elements to upcycle it! Love this comprehensive styling guide.

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Kelly Williams's avatar

I got my first AYR for Christmas (the silk Deep End!) and I’m already ready for more 😉

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Priscila Smith's avatar

Oh I don’t have a silk one! adds to wish list

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Lin's avatar

I can’t tuck my shirts anymore (too much work) so my workaround is wearing them open over a light tank top. Also mis-buttoning one or two or buttons gives a bit of the same effect as a messy tuck but the shirt needs to be billowing a tent for this to look intentional. Super enjoyed reading a post about one of my favourite wardrobe staples!

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Kelly Williams's avatar

I love the mismatch button, especially on a longer button down! Plus the beauty of a button down is that (IMO) it is better when crinkled/wrinkled. PS- your outfit in the chat showed a truly perfect button down outfit open over a tank.

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alison's avatar

j crew etienne button ups are what i live in year round. take your normal size and they are perfectly oversized. i have one in oxford cloth that i like wearing to work because it feels more dressy. i’ve also been stalking a bunch of polo and brooks brothers men’s button downs on poshmark since my husband is sick of me stealing his. it is a goldmine and prices are pretty much universally under $20

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alison's avatar

also recommend wearing a lacy bra underneath and button as low as you are comfortable - helps it feel more dressy/sexy for a night out. literally wearing that exact combo today!

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Kelly Williams's avatar

Yes!! Used men’s button downs are CHEEEEAP and amazing. I have been eyeing the etienne button ups from JCrew! Are you ordering your normal size in that or going up?

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maryse's avatar

I went nuts with the Etienne shirt. I’m embarrassed to admit how many I have. I agree. Order your normal size.

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Kelly Williams's avatar

THANK YOU!

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alison's avatar

yes - my normal j crew size!

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Robin's avatar

I’m super excited to try the diagonal tuck! I have never felt comfortable in any of the other versions (something about my short-ish waist on a tall person) but that may be my answer— thank you!

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Kelly Williams's avatar

Yay! I'm so glad you liked that tip; it's my favorite hack recently. I did it today and only took the corner to above my pocket so there was more volume to play with. Report back on how it goes!!

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Meighan Grady's avatar

Once again, I truly love your foray into the digital assets. These GIF/videos!? Perfection!!!! I just joined the GAP big shirt gang and cannot wait to wear it and wash it until it gets that perfect worn in quality. Until then, the cuff and scrunch is really the best way to make it look casual and lived in.

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Kelly Williams's avatar

Are we keeping the scrunch up with an elastic or are we keeping the cuff buttoned so it’s tight enough to stay?

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Meighan Grady's avatar

i personally cannot cuff more than once when the buttons are still done - so it will be elastic for me and my arms!

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Kelly Williams's avatar

I trust you 🫡

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Meighan Grady's avatar

Show me someone who can keep the buttons closed and I will envy their forearms 😂

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Anna Newton's avatar

Chiming in once again just to say Kelly, you are a genius!!! The diagonal tuck?! Mind blown x

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Kelly Williams's avatar

It has transformed my life (not to be dramatic 😉😂) but truly it’s the perfect tucking solution for what I want!

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