Underwear Shopping with Jake Gyllenhaal

Jake_gyllenhaal_2Via Page Six: “Jake Gyllenhaal is way beyond the simple choice of boxers vs. briefs. A shopper in Bloomingdale’s underwear department recently watched the Brokeback Mountain star with a salesman ‘combing through every style…A good 10 minutes later, Jake was still at it…holding up a pair of tight white briefs that he’d pulled out of the package to examine, as if he’d never seen tighty whities before in his entire life. It was hilarious. He looked very confused and had a furrowed brow…He was examining undies like an anthropologist in the city’s most highly trafficked department store.'”

Or maybe he’s just used to going commando.


  1. Matt says

    Even though Leland and I slug it out most of the time on Towleroad, we can both agree that Jake is HOOOOOOOOTTTTTT!!!!!

  2. Jeff says

    Uh-oh… This is probably MY fault. I told Jake not to come home without a pair of green Tiger of Sweden briefs he could wear on St. Patrick’s day. I guess the green ones were all gone by the time he got there (freaking leprechauns!) so he was wondering if maybe we could dye a pair of white ones.

  3. Gregoire says

    Jake likes quality and doesnt want an inferior fabric to rub harshly against his private parts.

  4. AMS says

    It sounds more like he was buying them for someone else. Someone who would model them for him later. We can only hope.

  5. Gore Vidal says

    He sounds like someone who has never had to buy underwear for themselves before. Either that or he has trouble with his eyesight and can’t see the label that says S, M. or L.

  6. kyle says

    Oh to be that salesman. I woulda had Jake tryin on every one of those…gotta check for fit

  7. gb says

    So true.The sign of a good salesperson.Try them on.Here let me straighten that out for you.

  8. atheist says

    “Ooh decisions decisions…”

    It’s a shame the shopper didn’t stalk Jake long enough to see what he finally purhased…One can only fantasize (about a jock…)

  9. Jerome Shipanik says

    Looks like Jake was having fun…..looking for a wardrobe for his next film?