David Beckham looked deep in conversation as he sat beside his high profile pal Anna Wintour at the BOSS fashion show during Milan Fashion Week on Wednesday.

The former footballer, 49, cut a smart figure as he opted for a navy suit and matching polo neck jumper.

Chatting with the Vogue fashion icon, 74, as the pair wrapped up for the outside show in the Italian city.

Anna looked effortlessly chic as she opted for a wine-coloured red floor length leather jacket.

Underneath the leather ensemble she wore a blue and white brushstroke patterned dress and her signature Chanel sunglasses.

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David Beckham looked dapper as he joined fashion icon pal Anna Wintour on the front row at the BOSS show during Milan Fashion Week on Wednesday

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The former footballer, 49, cut a smart figure as he opted for a navy suit and matching polo neck jumper

David Beckham and Boris Becker enjoy BOSS fashion show

Meanwhile Amelia Gray Hamlin cut a trendy figure in a pale pink denim jacket and matching low rise trousers.

The model, 23, flashed a glimpse of her washboard abs as she waved at fans in the street before completing her look with some black loafers, handbag and black shades.

She later changed into a black wrap shirt top and matching skirt as she took to the catwalk in business attire.

Newlyweds Boris Becker and Lilian de Carvalho Monteiro were also in attendance as they walked hand in hand following their wedding last weekend.

It’s not the first time the pair have been seen together, after they last posed together at the David BeckhamNew York City back in May. 

Meanwhile Anna was also sat front row beside David at his wife Victoria’s fashion show last September as she unveiled her latest collection.

Brooklyn, his wife Nicola Peltz, Cruz and Harper joined their dad on the front row for the ex-Spice Girl’s Parisian parade, along with Vogue editor-in-chief herself.

Discussing her and David’s shared love of fashion, Victoria recently revealed how the sportsman bought a brand new Prada suit just to ‘impress her’ on their first date after she said she liked the brand.

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Chatting with the Vogue fashion icon, 74, as the pair wrapped up for the outside show in the Italian city. Anna looked effortlessly chic as she opted for a wine-coloured red floor length leather jacket

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Underneath the leather ensemble she wore a blue and white brushstroke patterned dress and her signature Chanel sunglasses

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David looked effortlessly chic as he completed the all navy look with some black shiny brogues

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Amelia Gray Hamlin cut a trendy figure in a pale pink denim jacket and matching low rise trousers

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The model, 23, appeared to be in great spirits as she skipped along the street on the way to the show

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Newlyweds Boris Becker and Lilian de Carvalho Monteiro were also in attendance as they walked hand in hand following their wedding last weekend

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Boris opted for a light grey suit while Lilian wore a similar blue-grey blazer and tailored trousers

The fashion designer, 50, opened up about the beginning of their relationship in an episode of the new documentary In Vogue: The 90s, which started streaming on Friday on Disney+.

Gushing about her love for designer clothes, she recalled: ‘Versace, Prada, and Gucci, they were my go-to designers. What was it they were getting right at the time? I suppose they really understood the power of celebrity.

‘The Italians embraced that. When I first met David in 1997 he’d heard that I was the Spice Girl that liked the designer clothes.’

The former Spice Girl told the camera: ‘So, after me going to a couple of football matches and I would say, you know, me sort of like, pursuing him, he’d probably say me stalking him, we arranged to go out on a date together.

‘He’s like, “I don’t know what to wear, she’s the one who likes designer clothes,” and so he actually went out and bought himself a full Prada look for our first date, to impress me.’

Laughing, she added: ‘Which it did, because it was Prada.’

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Kaya Scodelario flashed her bra in a low cut white silk shirt and matching trousers

Jamie Campbell Bower looked effortlessly cool in an oversized black jacket and brown leather trousers

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German footballer Loris Karius took to the runway in a oversized navy suit and striped shirt

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Amelia flashed a glimpse of her washboard abs as she waved at fans in the street

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The star added some stylish black shades to the complete the ensemble

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The pair looked to be laughing as together as they watched the outdoor show

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David struck a serious expression at the fashionable event

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Amelia later changed into black business attire for the catwalk

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The models took to the catwalk as they showcased the Spring/Summer 2025 collection

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One model took to the catwalk in a brown leather pair of jorts

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The show took place outside in the gardens on a mirrored catwalk

Elsewhere in the highly-anticipated new documentary, Victoria revealed how she copied Linda Evangelista after becoming ‘completely obsessed’ with the supermodel.

She explained that she became so interested in the 90s icon that she went to the same salon Linda used and even emulated her haircut.

She said: ‘[Linda] was the reason why I cut my hair, the reason why I dyed my hair lots of different colours. I was in New York, and I went to Garren, who was Linda’s hairdresser.

‘When he cut all my hair off. I was channeling my inner Linda.’