Open to Buy: Button-Ups and Button-Downs

Why we all care about button-ups now.

After years of looking for the right button-up shirt (why button-up and not button down? We will get to that later.) I had given up all hope. None fit in the right spot to feel appropriate, the buttons were always popping open, if they were oversized it looked like I was a kid wearing my Dad’s shirts as an art smock. Nothing felt right so what was the point. Then I noticed some very cool button-ups. One was a Chava collab with Laurel Pantin that was a take on a tuxedo shirt. Eventually I planned a trip to Mexico City to explore the culture and food, but mostly to visit Olivia Villanti’s Tiendita for Chava. She’s since renovated it and already I want to go back. But having her measure me for semi-custom shirts helped me realize that the right shirt for me existed and I just needed to study up a bit. I’ve since also purchased from TWP (this one) and Attersee (similar), I’ve built a nice little collection. Part of it is learning the anatomy of a shirt and also understanding how they should fit.

But that isn’t the only reason I wanted to write a fashion spiral 🌀 on dress shirts. They are in the conversation right now. First there were oversized Frankie Shop shirts, but in Spring/Summer 2026 season we saw Matthieu Blazy in conversation with Charvet. Not a collaboration, they refer to it as a conversation. Which brought Charvet from niche to fashion mainstream. And if you were shopping Charvet maybe you heard through fashion Substack or another influencer guide that you needed to visit Lauren Rubinski’s new shop Rubirosa’s in Paris. So many people visited that it is already expanding about one year after opening. And as for the Charvet and Chanel conversation, they moved from talking, to dating, and finally to marriage this past July when Chanel purchased Charvet.

Chanel went from taking a shirt that started at Charvet for around $600 to about $4,350 to full on buying the company. But it makes a lot of sense and probably was the better option than a PE firm or other investor coming in. I have faith that Chanel will do right by Charvet. Recently Carson Griffith from Rich People Shit shared that the Chanel runway moment made the shirts so popular that there is no inventory to sell at the moment beyond custom. Eventually this will die down, but I don’t think our passion for button-ups or button downs is going anywhere for a bit so we might as well do a deep dive. What you will find here: a pricing matrix, the anatomy of a shirt, insights from the experts (aka the brands we all go to for dress shirts), cufflinks – because they matter now, reader questions and styling tips from another expert, plus plenty of shoppies and more content. Let’s get to it. Fashion Business School is in session.

In this send: A deeper look at button-ups versus button-downs, pricing, anatomy of a shirt, and let’s talk to the experts. Plus: Phillip Lim’s shirts, Uniqlo, Charvet, shirt conversations, fashion tape, cufflinks, Brooks Brothers, Thomas Mason, vintage Levi’s, yoke, placket, french cuff, gusset, With Nothing Underneath, Pip Durell, Frank & Eileen, Audrey McLoglin, AYR, Maggie Winters, Soldout.nyc, Kianne von Mueffling, ALC, Andrea Lieberman, Alex Mill, Alex Drexler, TWP, Trish Westcoat Pound, vintage Dior, Rubirosa, and so much more.

Request for the comments: Share your favorite dress shirt or any questions you still have and I’ll work to answer as many questions I can or find the resources who can.

The Shoppies! Dress Shirts

• Phillip Lim recently launched Play Love Win, a new dress shirt line.

• I have this sheer shirt, and in black it isn’t embarrassingly sheer. Still feels appropriate. I love it. So lightweight I can wear year round. [Use code Sarah15 for 15 percent off at Donni.]

• In ivory, this is a great sheer shirt.

• For a slightly feminine ruffle detail.

• Why mess with a classic? And this one might be the second most classic but the number one most preppy.

• This in the Grecian Blue is my next purchase. I take my size or a size down.

• Remember, there are JW Anderson dress shirts at Uniqlo prices. And C by Clare Waight Keller for Uniqlo Stand Collar Shirt.

• You can order Charvet online.

• This one is a best seller and priced sharp at $125.

Just a few of the shirts featured in this send.

You Asked & A Stylist Helped Answer

I’m sharing the stylist I use personally when I need help. Elyse Winter to the rescue. She is fantastic. And if you aren’t looking to work with a stylist, I still highly recommend following her on Instagram. I did for a long time before we took our relationship to the next level.

You asked: How are we tucking button-ups right now? We’ve been directed to go at various times from full tuck, to French tuck, to half tuck?

I asked Elyse Winters, and she broke it down to three options depending on the mood:

• Untucked, unbuttoned at the hem — leave it fully out and undo the bottom couple of buttons so it can move and flow. Err on the side of more loose and open.

• The half-tuck — line the buttons up to the center of your jeans, then tuck only the side of the shirt closest to your body. She texted me “a lot of people don’t do that, idk why.”

• Full tuck plus a belt — the most polished, most “done” version of the three. Plus then you get to add another accessory.

One tip she shared with me to help keep the shirt in place and not exposing more than you want to while keeping it unbuttoned, fashion tape**! Elyse has a great tutorial on how to use the tape here.

You Asked: Any button-up advice specifically for petite frames?

For petites (hi!) Elyse suggests High Sport, Attersee, Chava, Kallmeyer, and Comme Si. Same she would suggest for non-petites too. Her styling tip for us petites is to pair with tapered jeans or high sport pants and a kitten heel. (The Chava + these petite High Sport pants + these kittens are my uniform.)

You Asked: Oversized or fitted — and how do you buy one that doesn’t gap awkwardly at the bust?

I appreciate Elyse’s always honest and direct approach. She says, “I only do oversized, I hate fitted button-ups”.

If you are looking for something more fitted, I would suggest this classic one and just pay attention to where you button. I think J.Crew and Buck Mason have great options too.

Accessories for your shirt

I have been begging for more cufflink options. Jewelry brands should absolutely be expanding into this category. I’ve found some cool options on Etsy, The RealReal, and 1st Dibs (Elsa Peretti!). Anne Fontaine, the queen of women’s white shirts, has a large assortment. If you are a brand making clip-on earrings, I suggest experimenting in cufflinks some, just make sure they are discoverable or collab with one of the button-up brands featured in the experts section.

Prada men’s dirty cuffs brought attention to the area but I loved the cufflinks and want so many more options. I’d love to see something like Dries Van Noten’s necklaces turned into cufflinks.

Brooches are being used to turn everyday, classic shirts into something more. Think clasped at the waist with a bit of a pleat, doubled up on the collars, a cluster on one side — so many options.

Monogram the shirt. I love with my Chava shirts I did my initials on the body of the shirt vs cuffs or collar. But have fun on the cuffs and collars too. Go for a tonal color for something more subtle or stand-out with contrast.

How about an open neckline with a long tassel or necklace.

Belts for framing and securing a good shirt. My favorites are: Anderson’s and Déhanche (fun fact, Creative Director and Founder Erin Webb is also a co-founder of Nour Hammour).

And of course your bra matters when you wear a dress shirt, but that is a whole other fashion spiral 🌀 post from me.

👔 Quick note: I write a lot (too much good stuff to share!) If you’re reading via email only, you may need to click through to the web version or read on the Substack app. I promise it will be worth it. 👔

Glossary — Or what is the difference between a button-up vs. button-up

• Button-Up – The most basic term for any shirt that closes via a column of buttons down the center front placket (see placket definition below). An umbrella term and doesn’t pertain to the collar or cuffs, only about how the front closes. This one has plenty of sizes and lengths.

• Button-Down – This refers to a specific collar style where the points of the collar have their own tiny buttons that fasten to the shirt body. The purpose is to hold the collar flat against the shirt. This style was invented by Brooks Brothers in 1896 and borrowed from English polo players whose collars flapped when playing. Every button-down is a button-up but not every button-up is a button-down. Say that even one time fast and I’m impressed. Harder to find in women’s but this is a good one.

• Tuxedo Shirt – This traditionally formal shirt is defined by a wing collar (small and stiff with folded-down points) or a turndown collar paired with a pleated or piqué bib front. Usually finished with French cuffs. Originally designed for formalwear but today I say anything goes! Wear with vintage Levi’s. This is my personal favorite.

• Point Collar (Classic Collar) – The standard collar with no buttons and no exaggerated spread. Here is a classic with a classic collar. Contrast that with a…

• Spread Collar – A wider gap between the collar points. Originally built to leave room for a wider tie knot to sit open at the neck. Here is an example of this style of collar.

• Cutaway Collar – An exaggerated spread collar where the points sit almost horizontal. The most formal, most structured version of a collar. A classic version and a well-priced oversized option.

• Band/Stand Collar – A collar with no fold-down points at all, just a narrow band standing up around the neck. See an example here.

• Placket – The reinforced strip of fabric running down the center front where the buttons and buttonholes sit. This example has a covered placket, so you don’t see the buttons.

• Yoke – The panel of fabric across the upper back and shoulders. It is cut separately from the rest of the shirt body. In this example the back yoke is more prominent because the stripes are horizontal on the yoke vs vertical on the shirt body.

• Barrel Cuff – The standard cuff has a single layer of fabric around the wrist kept closed with one or two buttons. Simpler and less formal than a…

• French Cuff (Double Cuff) – A cuff folded back on itself to create a doubled layer of fabric, fastened with cufflinks instead of a button. Can also be worn open and free, just be careful when eating. Historically reserved for the most formal shirts, but not necessarily anymore. Fancy cuffs!

• Gusset – A small triangular fabric reinforcement sewn into the side seam at the hem opening at the bottom of the shirt to reduce fabric stress. Yes, even shirts can experience stress. A functional detail. In this example, the gusset details are more prominent.

Asking the Dress Shirt Experts

Similarly to how I reached out to Denim Experts for the Denim spiral 🌀 I reached out to brands that are go-to’s (for a good reason) in dress shirts. Each one I had different questions for. This uses more of my merchandising thought process to tailor the questions. Here we will get a fun mix of design, inspiration, fabrication and more.

With Nothing Underneath — Pip Durell, CEO & Founder

For Pip Durell and her brand With Nothing Underneath, after wearing this shirt* all summer I wanted to ask about the single horizontal button-hole at the bottom of the shirt. I also felt truly comfortable in a fittted-for-me but not too fitted shape and had questions for Pip around construction and how to get the fit right for a woman while still being inspired by menswear. WNU has so many options in silhouettes I think it is a great spot to shop for a classic fit without feeling like you are swimming in a shapeless men’s option. Consider it your shirt version of “strong enough for a man, but PH balanced for a woman”.

Sarah Shapiro: I noticed the bottom button-hole on the boyfriend shirt is horizontal vs vertical. Why was this important?
Pip Durell: It’s a nod to traditional menswear so it felt fitting for us as a brand – our core tenets are based in menswear; the subtle oversized nature of our clothing giving a nod to the men, while our tailoring, balance and attention to detail bring that focus to the female form.

Sarah: What details around the cuffs and collars were important?
Pip: Now that we have multiple styles and shapes, they vary – but the crucial point when making a shirt is the balance. Too small a collar is a crime, it’s not flattering on
anyone. Ditto small, meek cuffs. A wider, stiff cuff means business. I like to roll mine
and for them to stay that way, allowing the crucial skin showing on the wrists – never
not sexy.

Sarah: Shirt tail and length. How did you figure out the best fit for this style of shirt?
Pip: Our Classic shape is extremely popular and I think the length and curved hem play a huge part in that – it’s flattering on every body shape. Just long enough to skim the hips, a gentle curve to bring a touch of femininity but not too much to feel blousy. I personally love to size up 2 for a really oversized look — particularly when I’m
wearing a Denim or a Flannel as an overshirt.

Sarah: What’s the one detail from men’s construction you refused to compromise on
when translating it into a women’s pattern? And is there anything about it that
felt deliberately different because it’s designed for a woman’s body?
Pip: The part that was essential to keep was the collar. It needs to be large and stiff — the proportion play is endlessly flattering and when it comes to a poplin, it’s the sort of
shirt that effortlessly brings confidence and an aura of’ put together’ – even when
just thrown on.
In contrast the part that was essential to change was the button placement on the
front placket. Before I started WNU I wore men’s shirts daily to work but the
placement of the buttons never hit right for my chest — it was the first thing I focussed on when I started making my own. Placed just right so you can have an elegantly low neckline, the exposure of decolletage without showing your bra. Or, of course, the option to undo just one more for the evening.

Sarah: Business wise, what are the top 2-3 classic shirting styles for the brand?
Pip: It’s a real mix – but our consistent bestseller year-round is out Classic Denim. Made from the perfect mid-weight Denim it really is a perfect shirt. After that comes a white poplin always, and then seasonally it shifts. As we enter into autumn people love the drape of the Tencel and the subtle weight of a hemp.
As a brand we cover all bases for shirting from work to play and the material/cut mix
really reflects that in the way our customers multi purchase and come back again
and again.

Frank & Eileen — Audrey McLoglin, CEO & Founder

Frank & Eileen’s website has an excellent Button Up Guide.

Sarah Shapiro: What’s the one detail from the original menswear fabric/construction that you insisted on keeping when everyone told you it would be cheaper or easier to cut a corner for the women’s version?

Audrey McLoglin: The fabric. From the very beginning, we’ve believed that the fabric is the foundation on which great style and quality rest. It’s something we’ve never been willing to compromise on. We fanatically seek out the world’s finest natural materials (that traditionally were reserved for menswear) and partner with exceptional textile mills and manufacturers around the world to create fabrics that are beautiful, durable, and only get better with time. That commitment to exceptional quality and sustainability has been at the heart of Frank & Eileen since day one.

Sarah: Which shirt should actually be on someone's list right now — and why

Audrey: Eileen in our Vintage Stonewashed Indigo Denim. It's our number-one best-selling button-up. The relaxed, universally flattering fit and effortless California spirit make it the kind of piece you'll reach for again and again. Wear Eileen tucked into denim jeans, tied at the waist, or thrown over just about anything. The small-batch stonewashed indigo gives every button-up a one-of-a-kind finish that only gets better with time, gently fading and softening with every wear.

Sarah: Since Frank & Eileen has been in the “dress shirt” category for some time, is there a style that the brand had early on and still exists today with little tweaks?

Audrey: Barry was our firstborn button-up, and it hasn’t changed. It is still my favorite style to wear when the day calls for something fitted, but still comfortable, with the perfect touch of tailoring.

Sarah: I’d love to hear how the business around dress shirts for women has changed since the business launched.

Audrey: We started with one button-up in 2009, and currently we have ten available for purchase on-site and in-store. As a category, demand for beautifully made, perfectly imperfect button-ups in a variety of silhouettes and fabrics continues to grow.

Alex Mill — Alex Drexler, Founder

Alex Mill has both men’s and women’s shirts but for this interview I was most interested in the menswear portion.

Sarah Shapiro: Since this is a big category for men’s, how does Alex Mill not get over assorted and choose the right fit?

Alex Drexler: To your point, the shirting category is a very big category so you need to find what works for you. I think what many men do is find the right fit that works for them and then they buy multiples in different patterns. What’s great about men’s shirts is if you find the perfect fit there are often many options to choose from — solids, stripes, plaids, and the list goes on. Also, sometimes you might go with a relaxed collar and other days a button down collar depending on your preference. You can really try different ones on different days. At Alex Mill we have the Mill shirt which is our quintessential button down shirt and we always introduce new fabrics, colors, and patterns.

Sarah Shapiro: How does menswear inspire womenswear for the button up/button down shirt?

Alex: We all know men love a good uniform and have their go to pieces like button down shirt or a tee shirt. The idea is the uniform is what Alex Mill was founded on. And to a certain degree some women also love their uniforms including a classic poplin shirt. Or women want to diversify their closet and menswear is a part of their style

Many women love the idea of wearing menswear and the women’s boyfriend shirt is oversized and based on a menswear shirt.

Recently, Alex Mill launched a shirting assortment with heritage fabrics from the Thomas Mason shirting and fabric brand. It is worth digging into this company — they were founded in Lancashire, England in 1796 and has spent over two centuries creating fabrics for bespoke shirt makers. Now we now seeing more brands partner with Thomas Mason on their own assortment bringing the heritage fabrics to their own pieces.

For Alex Mill, these shirts were made in Italy from 100% cotton, the Thomas Mason fabric is lightweight, refined and easy to wear, while still maintaining the relaxed and lived-in quality of the original Mill Shirt. The new style is available in five striped colorways.

ALC — Andrea Lieberman, Chief Creative Officer & Founder

Another brand that has partnered with Thomas Mason. ALC believes in the dress shirt so much that there is a dedicated “Shirting” landing page in the navigation. This makes it easier to find, improves SEO¹ and help become a destination for this category. Andrea Lieberman shared more about the shirting and essentials at ALC.

“For me, a great button-down is one of the foundations of a wardrobe. My days are long, and I need pieces I know work. Things I can come back to over and over again. That was really the idea behind creating ICONS: taking the pieces I consider essential to getting dressed and making our version of them.

The Mason Shirt is exactly that. A great cotton button-down can be worn a million different ways, so it really comes down to getting the fabric, fit, and proportion right. It needs to have that beautiful crispness and structure while still feeling relaxed and comfortable enough that you actually want to live in it. We were very particular about the fabric quality for the Mason Shirt. We use 100% cotton from Thomas Mason, a European heritage mill that has been making fine shirting fabrics for over 200 years.

There are so many button-downs out there, and I don’t think it’s about reinventing something that’s already a classic. It’s about those little details that make you reach for one shirt over all the others. That’s also how I think about value. If it becomes one of those pieces you’re wearing constantly and styling a hundred different ways, then it’s doing its job.” — Andrea Lieberman

AYR — Maggie Winter, CEO & Founder

While AYR has great basics, their The Deep End shirt first came on my radar in 2021 when Oprah put it on her famous Favorite Things List. Maggie Winter shared with me that The Deep End isn’t even their key dress shirt style, it’s The Tate. This is a style is so popular it will regularly sell out. [Note from Sarah — rather than this being an inventory planning issue, I see challenges like this to be the unintentional hit of when an Influencer/Creator links to your product and it quickly goes viral.]

Maggie shared with me that their head of womenswear, Brigette Deshais, found a men’s Dior shirt at a vintage shop in Milan and the details like the sleeve and collar construction helped inform the styling of The Tate. The face framing collar helped become a signature of the AYR styling and fit.

Soldout.nyc — Kiane von Mueffling, CEO & Founder

I asked Kiane von Mueffling, CEO & Founder of Soldout.nyc, to share with me more about The Everything Shirt*, a style I own and wear in black. This shirt is oversized (but not impossible for us petites to wear). This shirt is crafted from 100 percent premium cotton. From the beginning, the goal was to create the kind of white shirt women reach for repeatedly. Not just because it looks polished, but because it feels incredible to wear. We spent a great deal of time refining both the fabric and the fit to achieve that balance of structure and ease. It’s become one of our most enduring best sellers because it delivers exactly what women want from a wardrobe staple: versatility, comfort, and a silhouette that always feels relevant. From Kiane, “A great white shirt is one of the hardest-working items in a wardrobe: timeless, versatile, and capable of making getting dressed easier.”

For Private Label readers: use code RetailDiary15 for 15 percent off at Soldout.nyc

TWP — Trish Westcoat Pound — Creative Director

I think of TWP as the go-to for non-classic dress shirts. Of course, you can find this, and this. More classic styles. But it is the plethora of fancy and more unique dress shirts for women. This shirt in Midnight was my personal first dress shirt from the brand. I liked the crop fit and the baggier fit (never have to work around buttons and where they hit). Figuring out how to re-button the sleeves was a little confusing at first but this helped. As for why TWP built out this category so much, here is what Trish Westcoat Pound, the brand’s Creative Director, had to say:

“When we launched TWP five years ago, it came out of a void I saw in the market for the perfect white shirt, and my own love of a woman in an oversized men’s shirt. I wanted to create something that could be both a workhorse and an investment piece, versatile enough to be worn with everything and still something you’d reach for years later. Every shirt is made with Italian fabrics from the best mills — quality and fit are what make a shirt worth investing in.

Women want a shirt that works as hard as they do, one piece that moves through her whole life without feeling like it belongs to just one part of it. We design into her lifestyle, it’s less about one specific look and more about a nonchalant ease.”

FYI, Trish Westcoat Pound has been building TWP alongside Andrew Rosen after previously working with him at Theory and on the Haute Hippie line. For an excellent podcast listen, check out this interview of Andrew Rosen with Emma Grede on her Aspire podcast.

Still Looking For More Content?

• Substackers love the blue shirt. See Libby McCurrach post here, Ardas Chandra post here, Scandi Delights post here, and I highly recommend Habitually Chic’s deep dive here.

• Back in December Lindsay Sword predicted we would need our irons for all the shirting. Check it out here.

• Ali Pew’s Uniform includes a blue and white striped button down shirt.

• Go visit Rubirosa’s in Paris. Or virtually, NYTimes gift link, and read Lynette Nylander’s piece here.

• FTHSI has a great article on Chava’s new tiendita.

• Last October I reported on Charvet for Puck’s Line Sheet.

• If you want to wear a pajama top as a dress shirt, they should be from Schostal in Rome.

• And if you need a suit or even just pants to go with the shirt, try here.

What’s Next

Sézane sent an email with recent FAQs on their rebrand. I was surprised to see the email which makes me think they heard the feedback and wanted to address it. Which led to more questions from me. I’ll be addressing this in my Tuesday send of Private Label. I have a few meetings and store visits in NYC next week, including more Channel Checks. Any requests?

Made just for you — always. See you Tuesday

xx, Sarah Shapiro

Private Label Issue 49

Catching Up:

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1. SEO = Search Engine Optimization — improving a websites discoverability for organic searches.