Like many other football fans around the world, I can spend hours upon hours browsing aimlessly through Classic Football Shirt websites. There’s something about looking at an old kit from the early 2000’s that can just take me back to a specific match, goal or moment in life which may have been long forgotten. Meanwhile, I enjoy looking through the wild designs that have somehow made it to production, the bold colours and pieces from around the globe. Although admittedly my personal collection of kits from the past doesn’t extend past my own club and holiday souvenirs, I am fully in support of the trend towards using “retro” shirts as a fashionable item, and for allowing me to spend far too much time in my own little world reminiscing on historic football games, long may the businesses continue.

So to celebrate some of my favourite football shirts that I have come across over the years, I’ve decided to put together my top 5 from around the leagues. This time, moving to one of the base countries for fashion, trends and style… Italy, and Serie A. Admittedly, this is personal opinions and not all tastes are the same, however I believe these are widely recognised as some of the greatest shirts from Serie A over the years. Additionally, as will become clear looking through these, I have a personal fondness towards a collared shirt, fairly simple designs and more ‘traditional’ colours to the individual club.

AC Milan 1988-1990 (H)

First up, is this legendary rosso & nero beauty from the late 80s in which AC Milan bagged back-to-back European Cups. With the Dutch trio of Gullit, Van Basten and Rijkaard linking up alongside the likes of Ancelotti, Maldini, Baresi… this squad has to go down as one of the strongest in history.

Despite being unable to continue their domestic success of 87/88 with this kit, the European success makes this squad renowned for their attacking and defensive strength. In 89/90 they missed out on the Scudetto by just 2 points, after a 2-1 defeat away at Verona on the penultimate game of the season.

The reason for this kit making the list of all-time greats is not just the history of the squad and their European success, but also for its style and beauty in design. On the precipice of Italia 90, this shirt was renowned for greatness, on-field and also off-field with it’s bold stripe design. With traditional colours, simple design and collared style, many football fans would agree that this is a real beauty.

Roma 2020-2021 (A)

The latest away release for Roma takes a beautiful ivory backdrop and places the throwback ‘Lupetto’ wolf emblem design on it’s chest, as the shirt pays homage to the Italian capital’s iconic monuments, history and outright beauty.

The clean design contains history as the Lupetto is a modern take on the kits from the 1970s, whilst the button collar makes reference to the kits from the 1980s. It’s a true masterpiece which deserves the success on-field, and will surely become a modern fashion statement for fans of all clubs. This is surely one to pick up at some point and wear the style of the Italian capital proudly.

What this season will bring for Roma on-field is really unknown. They have some serious talent in their squad, however with a 5th placed finish last season, and the re-emergence of both Milan sides to challenge Juventus’ dominance, it will be a big task to break into that top 2/3. They will however be in the Europa League where they will look to mount a serious challenge for the trophy.

Whatever happens for Roma on the pitch this coming season, they have already won my heart with this beautiful kit.

Napoli 1987-1988 (H)

Following their inaugural Serie A title in 96/97, Gli Azzurri sported this beautiful and historic kit, as they displayed both the Scudetto Shield and Coppa Italia badge on their jersey.

This iconic shirt was donned by the legendary Diego Maradona, as he scored 15 league goals in the campaign which failed to quite match the previous season and the resolute defence of Milan meaning they could only manage a 2nd place finish, alongside quarter final Coppa Italia exit to Torino, and losing respectably to Real Madrid in the last 16 of the European Cup.

This kit not only had one of the greatest players of all time donning it each and every week, but has become synonymous with the Argentine legend and the success he brought to Naples in the late 80s. This beautiful kit ticks off all my wish list criteria for a legendary football shirt; bold traditional colours, simplistic design, collared shirt, and has some marvellous historic context alongside. Owning this one is truly on my bucket list, and I would pay a scary amount of money to own one.

Juventus 1992-1994 (H)

Juventus have dominated the ‘kit’ game for about as long as they have the actual game of football in my personal view. They’ve had some belters over the years, however I have picked just 1 to summarise all of their classic beauties.

This one from 1992 has made my personal top 5 for several big reasons, firstly the collared style, the traditional black and white stripes and quite a simple design.

The 92/93 season was another one of failure in the domestic league, as shockingly by todays standards, Juve failed to win the league for the 7th straight campaign, and ended up in the UEFA Cup places with a 4th spot finish. Meanwhile they reached the semi-final of the Coppa Italia. The big success from this season is their UEFA Cup win, after the dominated Benfica and PSG on their way to the final, in which they won 6-1 over 2 legs against Borussia Dortmund.

Roberto Baggio again brought his magical kicks for The Old Lady, scoring 21 in 27 Serie A games and earning him the 1993 Ballon d’Or, alongside Di Canio, Vialli, Ravanelli, Conte and new signing David Platt.

Fiorentina 1998-1999 (H)

If there was ever an image to sum up the 90s, it would have to be Gabriel Batistuta lining up for Fiorentina in the wonderful violet ‘Nintendo’ kit.

It was a mixed season for La Viola, as they led the domestic league for a large portion of the season, only to crumble in the run-in to a 3rd place finish. Additionally, serious crowd trouble led to the disqualification of the side from just the second round of the UEFA Cup, despite having won the first leg 2-0. Certainly a ‘what could have been’ season for The Purples, however they looked bloody good whilst doing it.

As with the previous shouts, this one again ticks all boxes for me personally, it has bold traditional colours, the collared style, and an incredibly nostalgic kit. A real delight. BRING BACK FILA KITS!!!

Special Mention: Fiorentina 1992-1993 (H)

Another purple delight. This one had the 7up logo plastered across the front, with an open collar and crosshatched base. It’s a true beauty that unfortunately couldn’t out-do the renowned 1998-99 shirt but deserves some significant credit.

Let’s just not mention the away kit for that year… probably best to leave that one.