Meet the New Traditional Button Down Pinpoint Shirt

One of the fundamental rules of dressing — the line that separates just grabbing coffee from Monday morning meetings — is a crisp white dress shirt. It’s the great equalizer. Whether you’re buying your first one for a new job or panic-packing for a last-minute business trip, a pinpoint usually checks every box without breaking a sweat.

“We already had a strong pinpoint program, but last fall we tested a new silhouette with a slightly longer point collar,” says Senior Merchant Francesca McGraw. It’s a subtle tweak — blink, and you might miss it — but the response was anything but subtle. “Our goal is to become a true destination where you can get dressed from head to toe, whether that’s suits, dress shirts, or beyond,” she adds.

While the update may look minor on paper, the difference is in the details. The original version featured a long collar; this new iteration leans into an even longer point collar with a two-button detail that quietly channels vintage Ivy League campuses and a touch of old Hollywood polish.

Those two buttons make all the difference. You can wear it with a tie, without a tie, tucked in, or unbuttoned with jeans. It’s structured, but not stiff. “It feels relaxed without looking sloppy,” McGraw says.

We caught up with McGraw to talk about the old versus the new pinpoint dress shirts, why they remain true workhorse staples in any wardrobe, and the fresh ways she’s seeing them styled today.

Can you walk us through the design of the latest pinpoint dress shirt? What were you trying to do differently this time around?

Francesca McGraw: As a company, we’re constantly growing and evolving — and that goes beyond just neckwear.

We already had a strong pinpoint program, but last fall we tested a new silhouette with a slightly longer point collar. It was a super subtle change, yet the response was huge. Customers kept telling us how much they loved it, which really got the ball rolling. It pushed us to think about what other collar shapes, colors, and cuff styles we could explore.

That’s ultimately what led us to introduce this new style. The name is a bit long — it’s a traditional button-down collar with a slightly extended point — but that adjustment naturally creates a soft S-roll shape.

How does this version compare to the pinpoint dress shirt already in the lineup? What would someone notice right away?

FM: So, this one has buttons, whereas the long point is just that — a longer point collar that sits really well. The first thing you’ll notice is how naturally it falls on the body, especially at the collar. It doesn’t feel stiff or overly crisp. Instead, it has that broken-in feel from day one. It feels intentional, but in an easy, effortless kind of cool way.

The unstructured longer point collar is a standout detail. What makes that collar roll special in your eyes?

FM: I love how subtle the detail is. It feels relaxed without looking sloppy. The best word to describe it, in my mind, is effortless. That detail gives the shirt personality without trying too hard.

Was there a particular era or reference that shaped the design? Maybe a certain decade, old Hollywood influence, or even a classic Ivy League look?

FM: I definitely think there’s an Ivy influence, mixed with a bit of 1950s Hollywood. It really mirrors our knit polos nicely and has a similar vibe. There’s more emphasis on the collar, but it still has that softer look — it feels like a shirt that’s meant to be worn all day. It’s not a one-occasion piece where the collar gets wonky shortly after. Instead, it’s designed to have that worn-in, all-day feel from the start.

Stepping back for a second, what role do you think the pinpoint dress shirt plays in a modern wardrobe? Why does it still matter?

FM: I’d say it’s the quiet workhorse of the wardrobe. It perfectly bridges the casual-to-formal gap better than almost any other shirt. You can wear it to the office, layer it under a jacket, or dress it down with denim. Especially in the modern wardrobe, where flexibility really matters, it just makes sense.

How are you seeing guys wear pinpoint dress shirts today in ways that feel fresh? And personally, how do you like to style yours?

FM: I’m excited for this year because it feels like men are starting to want to dress up again. You’re seeing a lot more suits in the trend cycle, and ties are having a really fun moment — for both men and women. It’s an exciting time. It feels like people are dressing based on their mood again, which means you can actually have fun with your wardrobe.

With a traditional button-down collar, there’s so much versatility. It really adds to that sense of play.

One day, you might button it all the way up and wear it with a full tie for a touch of personality. The next day, you could leave it undone, open the collar, roll up your sleeves, and pair it with tailored pants. You can throw it under a jacket or sport coat — with or without a tie — and just let the collar do the talking.

I love how versatile it is, and how effortlessly cool it feels.

Let’s get a little technical: how is this collar actually constructed compared to a traditional fused or lined pinpoint dress shirt collar?

FM: Honestly, it really just comes down to the cut of the pattern itself. There’s no specific inner lining or fusing involved. We spent a lot of time dialing in the collar length and refining the proportions so everything would sit exactly where we wanted it to. There are a lot of upfront details that help create that effortless S-shaped curve.

What happens to an unstructured collar over time. How does repeated washing and wear change the way it looks and behaves?

FM: I actually think it gets better over time. With wash and wear, it softens the roll, which gives it more of a natural look. And I love a worn-in garment — I feel like it just gains more character as time goes on.

A lot of people say a longer point collar just looks better with a necktie. Why do you think that is?

FM: I feel like it’s because of the way it sits. It naturally frames the tie, if you will. There’s a little more space around the knot, whereas some collars might press up against it. Because it sits more comfortably, you look more comfortable wearing it — if that makes sense. And when you’re comfortable, you look cooler, because you’re at ease in what you’re wearing.

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