Rule number one: keep them smart. Perhaps if you live on Bondi beach you can get away with ripped denim like our superstar girl crush Elle Ferguson from Theyallhateus.com (we raided her wardrobe for last week's issue of The ICONS Update - do check it out), but for me they have to have a tailored feel to work in the city. I would also always pair with something a bit on the smarter side, like a buttoned down shirt or pretty blouse. Today I'm wearing my old J.Crew satin green shorts with a Gap denim shirt (buttoned up all the way) and tan accessories. Make sure your bag is a little smart too to add a sharp finishing touch (by the way my CHLOE Drew bag is back i stock!).