The relationship between celebrities and fashion advertising is at times perilous. A celebrity can add a layer of intrigue (and publicity) but associating the wrong person with a brand can spell disaster. While an original concept can make even the most overexposed celebrity seem vaguely interesting again – take the hilarious Victoria Beckham for Marc Jacobs ads which play on Beckham’s love of shopping and diminutive size by placing her in bags in and boxes. Most concepts don’t aim that high, were much more likely to see the average glamour shot in a star driven ad or project as opposed to a model one. Stars have reputations to uphold and as a result they are often less likely to do something daring. Or charming for that matter.

Band of Outsiders has found a smart way around this quandary with its star powered look books. Every season a recognizable yet under the radar face is shot by designer Paul Sternberg and featured in a series of vintage style polaroids wearing the trademark irreverent prepster Band of Outsiders look. There is a caught in the moment feeling to each shot that allows you to think you’re peering in on something private – whether its Bobby Birdman mowing the lawn or Jason Schwartzman in a laser tag mask.

This season’s book for Boy, the equally appealing Band of Outsiders women’s line is filled with portraits of Michelle Williams lounging around the Laurel Canyon home of interior designer Paul Fortune. She is seen answering the phone, pouring herself a nice glass of wine and settling down with a good book – all while dressed in the attractively retro tailored suits Boy presented for fall. Michelle’s series takes the pictures one step further and illustrates the effectiveness of the idea as a whole.The relative monotony of her actions within the ads show us that these are clothes meant for the day to day – not the untouchable perfection of editorial finery or the glamour of the red carpet. These are the clothes you wear when you’re being yourself. In addition to displaying the ease of the clothes Williams’ own unfussy chic suit the brand to a tee. Can’t wait to see which indie film style icon pops up on their blog next – my money is on a Gyllenhaal.