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?