Well, here's a challenge: how about an all-in-one baggy denim jumpsuit and construction boots?
RiRi sported her latest look while out and about in London (in case you're hoping to catch a peek of her in person, she was snapped walking out of the Corinthia Hotel) and her boyish street style wouldn't have been complete without a few key accessories, including a studded black cap with tartan fabric, dramatic chunky gold necklace and ultra-feminine swipe of red lippie.
Is it just us, or is she managing - against all odds - to make this work?
Let us know if this is another street style hit for Rihanna and don't miss RiRi's style evolution below.
By Jennifer Barton