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.
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.
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.'
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.'
