Reinterpreting Black Ivy

My journey with Proper Cloth

I’m not the first to be influenced by Black Ivy, and I certainly won’t be the last.

Jason Jules and Graham Marsh’s masterpiece documents how Black culture not only adopted the Ivy look but, more fittingly, made it their own. This “revolt in style,” as the authors put it, remains a defining moment in men’s fashion, with a lasting legacy that continues to inspire.

Whilst flicking through the book, the images that always stand out most to me are the vast array of button-down collars, all styled to perfection. Understated but worn with attitude, the musicians, actors, poets, and notable figures of Black Ivy didn’t merely adopt Ivy style—they made it better.

It’s a classic I wear every day. I’ve got plenty of them hanging in my wardrobe. Do I need more? Well, obviously.

This time, I took the inspiration one step further and went to Proper Cloth to help me recreate some of my favourite looks featured in the book.

Miles Davis’s L/S Popover Towelling Shirt

I’ve always loved this shot, and it has always fascinated me. The key thing to remember throughout this selection of shirts I’ve created is that I don’t want to make direct copies. Instead, I want to be inspired by them and put my own spin on each piece. That’s an important thing to bear in mind, particularly with Ivy style—because as soon as you try to recreate a look exactly, you’ll never quite achieve what you’re aiming for. But if you take inspiration from it, you gain artistic license, and there’s a much richer story to tell about where that inspiration came from.

It’s quite hard to tell exactly what fabric Miles is wearing here. It looks like it’s probably a soft jersey fabric. However, I love the idea of reimagining this shirt in a towelling fabric. Towelling was a popular fabric in mid-century menswear, particularly for warm climates, and I love the idea of a relaxed popover shirt that still adheres to Ivy principles. Rolling up the sleeves a quarter, pairing it with a cap, jeans, and loafers—it’s a look I can’t get enough of, and I plan to wear it almost non-stop this summer.

As you can see, there are some subtle changes compared to the one Miles is wearing. I’ve added a flap pocket, which is a detail I always prefer on shirts, whereas his features a regular patch pocket on the chest.

Terrycloth—sometimes called towelling fabric—is a material that makes perfect sense for this kind of piece. Originally developed for towels and bathrobes, it later found its way into mid-century menswear, particularly in warmer climates where breathability was essential. It was a practical choice but also had a certain understated elegance, appearing in everything from resort wear to casual tailoring.

What makes it ideal for this shirt is the texture. It’s soft yet structured, with just the right amount of weight to give it shape while still feeling effortless. Miles’ original might have been jersey, but towelling adds another dimension. It retains the ease of a classic popover but feels even more relaxed—without losing any of the refinement that makes Ivy style what it is.

LeRoi Jones (Amiri Baraka / Imamu Amiri Baraka) & His Check Shirt

This next look is directly inspired by a picture of LeRoi Jones (later known as Amiri Baraka), the playwright, poet, renowned jazz aficionado, and political activist. His style is something I’ve always admired, and there are two photos of him in Black Ivy that particularly stand out to me.

One shows him sitting outside his brownstone in Newark, New Jersey, in 1959—wearing a great pair of chinos, suede boots, and, of course, a chambray shirt. But the shirt that inspired me to create something similar is the check one he’s wearing here with a shawl.

Now, I’ve already got plenty of check shirts in my wardrobe, but since the original photo is in black and white, I can’t quite make out the exact colours. The greyscale tones of the image, though, pushed me towards creating a grey flannel check shirt—a more casual piece that could still be worn with a tie for a bit of a juxtaposed look.

Dizzy Gillespie’s Striped Number

One thing Black Ivy has in common with my wardrobe is that it’s not short of striped shirts. There are plenty in this book, and this one from the picture of Dizzy Gillespie really resonates with me. He’s captured the upper Ivy look, combined with the beatnik jazz musician vibe of New York—the pipe, the glasses, the bold jacket, and the tie bring the whole look together. But at the foundation is a perfect shirt: a striped shirt with contrast stripes.

I had a look at what Proper Cloth had to offer and found this great fabric. While it’s a bit more exaggerated in terms of the colours and stripes used than the one Dizzy Gillespie wore, it’s certainly in the same realm. I’ve already got lots of striped shirts—university stripes, contrast stripes—but one like this is just a great addition.

It’s versatile, serving as a perfect pairing to both a formal suit or a more casual outfit. You could easily wear it with a suit and a darker tie, or on its own with jeans. It just works really well because the stripes break it up. If it were just a white shirt, it might feel more difficult to pull off, but the variety of colours makes it playful. This is a great Oxford cloth button-down.

To wrap things up, what Black Ivy represents to me isn’t just a style, it’s a way of approaching fashion with intent, creativity, and a deep respect for the figures who made it their own. Taking inspiration from the likes of Miles Davis, LeRoi Jones, and Dizzy Gillespie is a reminder that style isn’t just about copying looks; it’s about reinterpreting them in your own way. It’s about taking those iconic pieces—the button-down collars, the check shirts, the contrast stripes—and making them yours.

For me, each of these shirts I’ve created isn’t just an homage to the past; it’s a reflection of how these influences continue to inspire my wardrobe and my approach to dressing. Fashion isn’t static, and Black Ivy proves that. It’s about the stories we tell through what we wear, the cultural exchanges that shape our style, and the ways we can honour the past while still making it fresh for today.

I’ve learned a lot from exploring these looks, and it’s a journey I’ll continue. And maybe, as you read this, you’ll find a bit of inspiration, too. Whether you’re discovering Ivy style for the first time or revisiting it with a new lens, remember it’s all about finding your own take—creating something that speaks to who you are now. So, if you’re feeling inspired, go ahead and take a page from Black Ivy. Make it your own, and wear it with pride.

If you’re interested in creating your own shirt, Proper Cloth offers a great platform to do so. You can choose your fabric, customize the fit to your measurements, and pick the details that suit your style. For a little extra help getting started, you can use my code TOMHOY10 to get 10% off your first order. Check out my curated gallery via the link here, and start designing your perfect shirt with Proper Cloth.