Kendall Roy as played by Jeremy Strong in HBO’s Succession has given us more than just great family drama. His wardrobe throughout the series has shown us a billionaire heir who balances luxury with accessibility. The Kendall Roy Shearling Jacket in Season Four was an instant fan favorite and I’m here to help you recreate that exact same outfit with all the five must-have items. Over four seasons we’ve seen Kendall’s style evolve along with his character. Every outfit tells a part of his story. I’ve spent hours studying these outfits and I’ll show you how to put together one of his most iconic looks. Let’s break down each piece of this outfit and figure out what makes it work.
A Little Bit About the Kendall Roy
Life isn’t easy when you’re the eldest son of a Logan Roy. Between fighting for his father’s approval and trying to prove himself worthy of the Waystar Royco throne, Kendall Roy has developed a style that says a lot about him. Throughout Season 4 we see him effortlessly balance his billionaire status with an approachable image that’s all his own. If you’ve been watching Succession you know Kendall’s journey is a rollercoaster. His clothes reflect that. He’s all business in perfectly tailored suits. But it’s in his downtime where his style really comes alive. These are the moments when his wardrobe shows us a more real version of himself.
1. The Fabulous Kendall Roy Shearling Jacket
What you will love most about Kendall’s casual style is that it never feels contrived. Even when he’s wearing pieces that cost more than a car, there’s an ease to his look that makes it feel achievable. This is a man who could wear anything money can buy and yet he chooses pieces that help him maintain that subtle sense of luxury. The Kendall Roy Shearling Jacket from allamericanjacket is the centerpiece of this look. This jacket is everything about Kendall’s casual style. The real leather exterior says quality without saying it while the faux shearling lining adds warmth and polish. It’s the kind of jacket that looks expensive and feels luxurious.
So let’s get into the details. The brown color is perfect. It is rich enough to look fancy but neutral enough to go with everything. Moreover, the zipper is modern and the shearling collar is just the right amount of fancy without going too far. Those four pockets aren’t just for show. The two exterior pockets are perfect for warming your hands on a long walk through Manhattan, and the interior pockets are for your phone and wallet.
2. Gray Crewneck Sweater
Under the Kendall Roy Shearling Jacket, a gray crewneck sweater does all the work. Don’t get an average mall sweater. You’ll want a sweater with premium cotton or wool that drapes beautifully. The key is finding that sweet spot between quality and subtlety. The sweater should feel amazing when you put it on, but not look like you’re trying too hard. The gray is a deliberate choice. It works with the brown jacket and creates that layered look Kendall does so well. The crewneck keeps things clean and simple. No extra details to distract from the overall look.
3. The Denim Jeans
The blue jeans in this outfit may look basic at first glance but it sets the tone for the whole outfit. Look for a medium wash that is not too light or too dark. The fit should be slim so you have room to move but still look clean. What makes these jeans special is the quality. You want denim with a little stretch for comfort but holds its shape all day. The wash should look natural and these jeans should look like they cost money without the obvious branding or designer labels.
4. Gray Baseball Cap
Even a baseball cap serves multiple purposes. It’s both a shield from unwanted attention and a way to seem more approachable. The gray matches the sweater so it looks planned but not too much. When choosing your cap, go for quality over branding. Get something made from premium materials with an unstructured design. Remember, no logos and no flashy details. The gray should be the same as your sweater.
5. Minimalist Sneakers
To finish the look off Kendal goes for minimalist sneakers in neutral colours. This grounds the outfit with a modern touch. Clean and simple sneakers tie everything together without taking away from the jacket.
Bonus:
I know this sounds weird to include posture in an outfit Kendall’s body language is just as important as the clothes. With hands in the front pockets of the jacket, he looks so laid back and cool. This stance adds to the overall vibe of the outfit.
Styling Tips to Nail the Kendall Roy Look
1. Every piece Kendall wears fits like a glove. Tailoring is nonnegotiable if you want to look like him. Make sure the outerwear you wear is not too tight or too loose. A well-fitted outfit makes you look better.
2. Kendall’s style is proof that basics don’t have to be boring. High-quality fabrics and minimalistic designs are key. A soft crew neck sweater, a well-made jacket, and premium denim can be the base for many outfits.
3. When it comes to accessories, a simple watch, a plain baseball cap, or sunglasses are enough to complete his look. Avoid anything flashy or over-the-top.
4. It’s not just what he wears, it’s how he wears it. His slouchy posture and hands in his pockets is part of his cool and calm vibe. Confidence is the ultimate accessory to any outfit.
The Bottom Line
You can wear this outfit to business meetings or to family dinners. It works because it hits that sweet spot between looking put together and feeling comfortable. The Kendall Roy Shearling Jacket outfit shows us that luxury doesn’t have to be loud to be effective. Remember style is more than just copying someone else’s look. It’s more about making it your own. Take these elements and apply them to your life.