Sydney Fife: Style Icon

We finally got around to watching I Love You, Man last weekend. It’s very funny, very cute, has great actors, a great script, and an adorably awkward man almost every woman wants to marry (Paul Rudd as Peter Klaven). What surprised me about the movie was how much I loved the style of sloppy mismatched Sydney Fife (Jason Segel). What surprised me more was when we went shopping the next day and The Boy told me he really loved Sydney’s style and wanted to emulate it. :D

Next thing I know he’s buying a hooded grey knit sweatshirt and I’m planning his wardrobe. I love being with a guy who is enough into fashion that he cares about how he looks and thinks about his purchases, but still relaxed enough not to look like preppy douchebag (I like preppy style, just not preppy douchebag style).

This one’s for The Boy, and anyone else who wants to get the Sydney Fife wardrobe.

Board shorts should be refined to the water and ugg boots should be kept inside. So really I should be screaming NONONOOOO at the thought of this outfit. But Sydney makes walking a small dog along a board walk in both board shorts and uggs look like the best idea in the world.

Sydney Fife - I Love You, Man - Ugg boots and board shorts

Start your Sydney wardrobe with some kitschy board shorts, low cut uggs, and a cowboy check shirt.

Sydney Fife - I Love You, Man - Tweed jacket and jeans

Add a grey tweed jacket, a light coloured striped sweater, jeans, and slip on shoes.

Sydney Fife - I Love You, Man - Cable knit cardy

Shop for a tux or relax with a beer in a shawl neck cable knit cardigan and t shirt.

Round it all off with a couple of scarfs and some more buttoned shirts, especially cowboy check shirts in yellow and blue tones. And there you have it, your very own Sydney Fife-d wardrobe.


Would you “let” your man dress like Sydney or dress like him yourself?

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17 Responses to “Sydney Fife: Style Icon”

  1. Jaka Merriman Says:

    When left to my own devices, I totally dress like Sydney, although a little more girly and no damned Uggs! :3

  2. Ms Constantine Says:

    The uggs are no longer allowed to be worn by women outside the house!
    I declare that they are only allowed to be worn by male Sydney Fife look alikes.

  3. The Boy Says:

    Yeah the Uggs are a bit much but the pink “coloured” striped sweater is definatly possibility!

  4. Ms Constantine Says:

    Is pink no longer a colour? I’m confused by your comment.

  5. Poppy Says:

    My guy is completely uninterested in fashion. Which isn’t to say he can’t dress himself, but he just wears nice sneakers*, jeans and a t-shirt. His most “edgy” item of clothing is a raspberry-coloured polo shirt my mother bought him for Christmas.

    He doesn’t really care what he wears, but I think this style would be too out-there for him (particularly the cardigan). I don’t force him to dress in any way, and don’t mind what he wears, although his denim jacket has never been seen again since our first date.

    *I say nice sneakers meaning the type of sneakers you don’t exercise in. I cannot STAND running shoes being worn when it is not running time. That is pretty much the only thing he would be forbidden to do (and thankfully, he doesn’t.)

  6. Ms Constantine Says:

    Lol, good call on the runners and denim jacket!

  7. SARAH HANNAH Says:

    rah no uggs outside the house ever!!! unless its like walking to get the mail at the front gate. my boy dresses like a douchebag. i have NO clue how to help him- i suck at boy dressing. my ex is my idea of boy style, and i cant exactly just dress my current boyfriend like him can i. can i? haha

  8. Chickie Little Says:

    I’m wearing pink ugg boots right now – inside. I’m also wearing a robe…

    Being on the board walk might help with Sydney pulling off the board shorts. Not sure how practical ugg boots would be outside, let alone anywhere near water!

    So when’s the Boy getting a paif of uggs? :)

  9. Ms Constantine Says:

    Me too, except my ugg boots are black, and my robe is pink.

    The Boy says with a frown “no ugg boots”.

  10. Em Says:

    Sidney Fife is god! Best wardrobe for a male movie character Ive ever seen. I so loved the rocking scarves and blazers <3

  11. Rabbit Says:

    Ooh glad to see you enjoyed this film as it is in my netflix que. I love that you made a dude fashion post, y’know there are really no fashion-boy-blogs out there, what gives?! Should us lady-bloggers set up our respective mens to create the first ever dude fashion blog? Okay so that kinda sounds like a recipe for disaster…but a cute one!

  12. Tash Says:

    I just watched the film last night and I was like “I love this man”. I want to dress like him. My partner said I’d be like an old man, but I don’t care, cause I’m hip like that.

  13. Tash Says:

    God, I just realised I emulated the title of the film. Ignore that.

  14. Ms Constantine Says:

    Boys are too busy trying to figure stuff out for themselves, not asking for directions etc to think of writing blogs I guess. :D

    My guy can’t spell so he’s a writing disaster waiting to happen already!

  15. Ms Constantine Says:

    Maybe his old clothes need to mysteriously disappear and you can hurriedly replace them with your own choices.

    That’s kinda mean, but desperate times call for desperate measures.

  16. Miriam Says:

    I love the looks, does anyone knoe where can i get the shawl neck cable knit cardigan??
    Thanks

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