We all know about the masculine look that we see women doing; it CAN be cute, depending highly on SKILL to not look 'mannish.' There are several items out there in shopping malls that are 'masculine' for women but still is nice-looking on the figure. For example, BOYFRIEND JACKETS, BOYFRIEND BLAZERS, BOYFRIEND SHORTS are the look to go after (See examples below) indefinitely in this category.
Unfortunately, it was very obvious that Janet Jackson (Ms. Jackson if you're nasty LOL) was trying too hard and ended up on my infamous 'FASH, CRASH, AND BURN' posts. She literally made herself look like a "Men in Black" in Louboutins. She was seen attending the second trial of Dr. Conrad Murray, accused of killing the late Michael Jackson with an overdose of Propofol. However the ITEMS she picked--not the whole outfit, just piece by piece--was pretty nice.
She wore Tom Ford "Whiney" sunglasses valued at $380, an Alexander McQueen skull print tie for $175, and Christian Louboutin stilettos for $700+. She also carried a tan Hermes bag. Check out some more pics of her.