


Jake was No. 2 in Esquire's Best Dressed Men of 2005: 'He's a beacon of light in young Hollywood, preferring the look of American classics rather than tawdry Tinseltown trends.' The Editor David Granger said of Jake: 'It's great to see a young man in Hollywood who actually cares about what he looks like.' Granger had an interesting recommendation for the type of shoes men should wear for public life: '"An American brand," Granger says. "Make sure they're solid so they make you look substantial, not too slight."'




In 2006, People awarded Jake with Best Insouciant Style: 'Looking casually thrown together is an art, and Jake Gyllenhaal the master.' It's not easy to say, either.

'Design consultant and celebrity stylist' Edward O'Sullivan said in 2007: 'I loved working with Jake Gyllenhaal, Patrick Dempsey. They're genuinely nice people and totally got the art of red carpet dressing.'


Mind you, it's not surprising Jake dresses so well, he gives it thought. He told the Sentinel in January 2006: 'The people that I respect all say it's all about tailoring. The men that I respect look good in suits that fit them. They're not afraid to ask the tailor to change them. Same with scripts. I want it to fit me.'




Jake was also quoted in Fabric magazine as saying 'I think of a role as a suit that I’m trying on and I have to make it fit me. I just wish to represent myself. If you give me a suit that’s too large, I’m not going to gain weight: I’m going to tailor it to fit me. That’s a metaphor for how I act and I feel it’s therapeutic for your life. Even if I’m playing a particularly intense or affecting character, like I did in Jarhead or Brokeback, I can always see my way back to my own self.'




Talking of public events... On December 10 2003 Jake attended the NYC premiere of Mona Lisa Smile along with Maggie and Kirsten. 'Jake has probably more reason to be here than anybody,' said Maggie. I rather liked this anecdote... 'In New York, Julia Roberts and her “kittens” — Julia Stiles, Maggie Gyllenhaal, Ginnifer Goodwin and Kirsten Dunst — celebrated the premiere of “Mona Lisa Smile” at the Plaza. A radiant Roberts flitted around the hotel ballroom in Chanel and a scent that made the men — or at least Maggie’s brother, Jake — swoon. “You smell so good,” Jake told Roberts, before giving a congratulatory hug.'


On the same day, one of my favourite pictures of Jake was taken on the streets of New York.

Includes pictures from IHJ.