LMAO, most likely, but if he wants you to look good then work it gurlfriend (that was the gayest thing I've ever typed, I apologise)
I just noticed LMAO, I love his defense mechanisms, my Will Young debate with him was flawless.
And not necessarily, you'll probably see that a darker colour of jeans will compliment the upper half of the outfit, but I'd just try on a couple of different shades of pair and see what looks best.
I'm going all Gok Wan, are you impressed?
