We’ve all seen it. The blue t shirt with bold red letters reading WIN “ROCKY” WIN. And we’ve seen Sylvester Stallone as Rocky Balboa wearing it for the briefest of moments during the training montages in two of the Rocky movies.
But what’s the story behind this shirt?
The one and only time we ever see Rocky wearing this t shirt on film is in Rocky II when he’s skipping rope in Mighty Mick’s Gym. In this scene, Rocky pairs the shirt with his Tuf-Wear shorts during the training montage.
Still photographs exist showing Sly wearing the tshirt in the original Rocky as he works the speed bag and Mickey times him. Such versions of this scene were ultimately not used in the final movie – only a closeup shot of Stallone’s face is shown as he trains on the speed bag and this is the only time in the original film that any portion of the shirt can be glimpsed – just the tip of the tshirt’s blue collar and shoulder tops are visible in this brief moment of the movie.
THE ORIGINAL ROCKY SCREENPLAY EXPLAINS IT

Unused Scene from Rocky
So where did Rocky get his t shirt? The story behind the shirt is actually a charming one.
In the original screenplay and novelization for Rocky, a scene is included which takes place around Christmas in which Adrian comes to Rocky’s apartment at night. With her, she brings a paper bag which contains colorful curtains to brighten up Rocky’s depressing room.
“Like?” Adrian asks proudly.
“Sharp, real sharp, real nice,” Rocky answers.
After a moment of romantic tension where Rocky tells Adrian they can’t fool around because – you guessed it – women weaken legs, Adrian “uncharacteristically removes her sweater” to reveal a t-shirt that says WIN ROCKY WIN.”I thought it might be cute,” Adrian says shyly.
Laughing upon seeing the tshirt, Rocky replies: “Ya’ right. Mebbe we best just hold hands – the shirt made me feel guilty, y’know.”
THE WIN ROCKY WIN TSHIRT AS FILMED. AND SCRAPPED.

Obviously, this scene never made it in into the final print – it was shot, however, and we can get a good feel for what it must have looked like on film from a few remaining black-and-white photos which still exist from this scene. Based on the wardrobe that Stallone and Talia Shire are wearing in the cut scene, this moment was most likely intended to take place immediately after the scene that DOES appear in the movie in which Rocky finds Adrian and Butkus waiting on his doorstep. You’ll notice Talia has a brown paper bag with her which they carry inside the apartment.
The still photos show Talia still wearing the attractive rust-orange fur trimmed coat and white beret she stunned Rocky with on his doorstep; Sly is seen wearing his trademark black leather jacket and then removes it before he approaches Talia.
What’s interesting is that rather than following the script to the letter, this scene was evidently improvised during filming. Rather than removing her sweater (or coat, in this case) to reveal the blue t shirt, Adrian pulls the shirt from the paper bag and sweetly holds it up for Rocky to read. Though just a slight change, this action seems a bit more in keeping with the Adrian character that was ultimately shaped by Talia Shire.
Had this scene made it into the original Rocky movie, we’d all know the WIN ROCKY WIN t shirt as the Christmas gift that Adrian had designed especially for Rocky to support and inspire him.
ROCKY II & APOLLO CREED’S TSHIRT
Fast forward to Rocky II, and we finally get to see Rocky actually wearing the shirt – this time with the sleeves cut off as he jumps rope in Mickey’s Gym. You may also notice that Apollo Creed wears a similar shirt during his sessions with the movement ball in the gym – his blue tshirt reads THE STALLION IN TWO, in large red letters, just like Rocky’s. We can only guess the reason why Carl Weathers is shown wearing this shirt, but it could possibly be a part of Apollo’s plan to intimidate Rocky – it’s conceivable that Creed’s team found out about Rocky’s inspirational shirt and had a competing one made for the heavyweight champ.
The final takeaway from Rocky II? The fact that Rocky’s t shirt embodies exactly what Adrian whispers to her husband when she awakes from the coma … WIN.
BUY THE ROCKY TSHIRT
Reproductions of Rocky’s tshirt are available online at Amazon, styled for both men and women. Take your pick from the options below!