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The 5 Most Recognisable AC Milan Shirts Ever

From afar, I fell in love with this football club and some of these AC Milan shirts really do bring those memories streaming back – and at great speed. So, this Hobby FC list ought to come with a disclaimer: from this point on, a nostalgia warning is in full effect. A lack of self control may lead to a bill you’re not going to enjoy looking at. 

Because not only are we going to look at the different jerseys that fans remember, but also the players who carried them better than most of their teammates.

Why are AC Milan Shirts so Iconic?

Well, it’s because this is AC Milan we’re talking about.

Technically, they’re not the most successful Italian side of all time (Juventus have that title for now with 36 Serie A titles at the time of writing), but if anything – I think this helps.

I have this weird saying, where I find certain clubs a little … antiseptic.

By this I mean that it doesn’t really make me feel anything. Clubs like these are burdened by money and almost synthetic in nature. I want a club that goes through the motions, so that I can go through it with them and look back wistfully at that journey.

No Italian club embodies this rollercoaster journey of success better in my mind than the mighty AC Milan. Which couldn’t have been possible without players like these.

George Weah (1995-2000)

I can hardly think of a better place to start than with this man.

Arguably one of the most significant strikers to ever play the game.

Before AC Milan shirts and Ballon D’Ors were on the agenda for the proud legendary Liberian, the odds were stacked against him even becoming a footballer at all.

Like something out of a ‘GOAL’ movie (wonderful flick, by the way), George Weah’s rise to the top found its way through a scout happening on a few of his games and then reporting his progress back to one of his mates back in France.

His mate turned out to be fledgling Monaco manager, Arsene Wenger.

A move to Monaco followed, then a breakthrough opportunity at PSG before an all-conquering AC Milan came calling under Fabio Capello in 1995.

The ‘defensive manager’ forewent some of his non-attacking tendencies to grease the cogs of a machine tailor-made to bring the best out of his new marksman, and Weah didn’t disappoint – laying siege to all that lay ahead of him before bringing home the gold.

That ‘Opel’ sponsored AC Milan jersey reminds of all of Weah in his pomp, and there hasn’t been another visage more suitable to his dominance than this one.

Whilst he might have rejected one of those more typical moves to Major League Soccer in America (at a time when it wasn’t really there to accommodate it), the time did eventually come for George Weah to leave his fabled stomping ground as age began to catch up with him in the early 2000’s.

Transient moves to Chelsea and Manchester City took his talent on tour but nothing more than that. For while England might have been treated to the ‘curtain call’ of Weah’s career, fans of Il Rossoneri were lucky enough to have been there for the main event.

Ruud Gullit (1987-1994)

Now, Ruud Gullit also wore that famous ‘Opel’-sponsored jersey.

But that ‘Mediolanum’ kit hits different.

The old Adidas sponsor, the classic stripes of AC Milan and the contrast of that bright number ten sprawled across his back is the stuff of Milanisti legend.

The famous dreadlocked Dutchman completely transformed the trajectory of the club when he arrived there under Berlusconi’s admission. Then, his classic link-up with compatriots Marco van Basten and Frank Rijkaard took things to another level.

Together, they didn’t just make winning football matches an efficient affair, but also a beautiful and fashionable one. They were each very stylish footballers.

Having said that, Ruud Gullit most certainly leads that flair statistic.

Gliding through the grass, caressing that footballing and letting the rest become history, his look and style embodies what was a truly glorious time for the San Siro faithful.

And it’s because of this, that of all the AC Milan shirts, his probably brings back the most vivid memories in terms of pure, brash, unadulterated success – both on a domestic and international level in the glory years learning from Arrigo Sacchi.

His title as an ‘immortal’ is a deserving one, to say the least!

Andriy Shevchenko (1999-2006)

We just spoke about one of the world’s favourite strikers in George Weah.

Now, let me tell you about one of mine; Andriy Shevchenko.

There’s another word I use regularly, and it’s best used to describe players like him. And that word is: ‘inevitable’. That’s right – I think Thanos stole that one from me.

I always felt that watching Andriy Shevchenko bear down on goal meant that a goal was completely unavoidable by the end of the move. It’s a word I use in a similar tone with the likes of Ronaldo (Nazario), Thierry Henry and Ruud van Nistelrooy. You scour the score lines and it was just inevitable that you’d find their names on that list. As are the others on this one written by Bleacher Report.

Now, Andriy Shevchenko’s name is brought up in a lot of different conversations and some of them seem to take the shine away from his time up front in his range of AC Milan shirts.

On a less savoury note, a poor move to Chelsea has somewhat dampened his legacy.

Since then, he did return to Milan briefly before home for good with Dynamo Kyiv, as we briefly looked at in this feature about his rookie sticker. And, if you’re up to date with current events, you’ll understand it became a theme in his post-playing career. As he became a voice for the Ukrainian cause.

It’s amazing what he’s doing now, and it really speaks to the credibility of the man he is, and I’m glad that he’s supplemented his playing legacy in such a wonderful way.

Now, fans have another reason to want to wear his name about in public.

Not least for that famous Champions League penalty conversion against Juventus which set Carlo Ancelotti’s era off to the best start possible. But let’s not talk about Istanbul

Kaka (2003-2009)

Did you know that Kaka isn’t his real name?

You probably did. But do you know where it comes from?

Well, his real name is Ricardo. However, his younger sibling found it difficult to pronounce that as an infant and in their attempt, the phonetic ‘Ka-Ka’ sprung from their mouth.

The future playmaker found it so endearing, that he chose to adopt it as an alias.

From that moment ‘Kaka’ was technically born, and he bore that name on the back of his shirt right throughout his career. Beginning with a precocious start to football life in the bowels of South American side Sao Paulo, to the glitz and glam of Italy’s fashion centre.

Speaking of fashionable, Kaka had this natural aura of calm and grace about him which immediately wormed its way into the hearts of his fans almost from the word ‘go’.

Soon, his ‘going-spare’ Kaka-22 nameset was printed on AC Milan shirts worldwide.

Of all the options on this list, I’d go as far as to argue that he might have the most aesthetic nameset of any of the players I’ve spoken of already – with the exception of Shevchenko who enjoyed the same look towards the end of his Milan career.

Instead of the bright white that both Gullit and Weah had on the back of theirs, the powers at be in the AC Milan boardroom opted for a gold decal which has stood the test of time.

With that, Kaka eventually made that jersey not only a visually spectacular choice for AC Milan fans, but also one that they can remember with some positive memories too.

He helped put Istanbul to bed. And made that revenge in Athens a reality.

Paolo Maldini (1985-2009) Yes. Really!

There aren’t enough words or numbers in the world to describe nor quantify the legacy the great Paolo Maldini has left (and is continuing to leave) on this incredible club.

Put it this way – he’s played with each of the aforementioned players.

In a career spanning two decades and a return of a trophy every single season.

What’s better is that he’s kept the same visage and number right throughout his tenure there, and joins a very exclusive list of players whose AC Milan shirts are retired.

As long as the club remains in safe hands for the near future, it’s looking as though there won’t be another Rossoneri representative to wear that famous number three.

And quite frankly, that’s all she wrote on this one.


Altogether, a number of great players have worn AC Milan shirts.

It sort of goes with the territory when representing this institution.

However, each of these have had careers which not only included spending their prime time over there, but also overcoming adversity to come out on the better end.

I didn’t want to put this in a specific ranking as that would be practically impossible, but there’s no getting away from the fact that these men are unequivocally recognisable and beloved characters in the rich and illustrious history of Italian calcio as a whole.

Well worth adding to your collection if you’re a fan of European football, and also a piece of high-end fashion with the trends moving in favour of pieces like these.

Which of these AC Milan shirts would you most like to own?

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