See Smart Questions #1 – 3 & #4 – 6

BCBG change room, probably one of my favourite places on earth (I was trying on the pants).  The blouse is from BCBG 3 years ago and the cardigan is GAP.

Smart Question #7:  Does it fit the way you want it to perfectly?
Depending on the look you want to achieve, you might need an item to fit skin tight, just right, a little baggy or downright oversized.  Think about this.  Don’t be restricted by the sizing on the item.  XXS and XL can work equally well for different reasons.

Smart Question #8:  Does it flatter your shape?
Great!  That pair of skinny jeans fits your thighs like a dream, but are you sporting a muffin top?  I know we all want to try our hand at must-have items of the season, but we have to be honest about our bodies too.  A good example of this is my search for a narrow-legged suit pant for work.  There were ones that fit me quite well, but I had to step away because they made me look emaciated.   Great for the runway, but not so hot for the work place.  Don’t pick up anything that gives you a bad “shape”.

Smart Question #9: Is it unique (to what you already own)?
Too often we gravitate towards clothing we already have.  Our eyes love what is familiar.  Honestly, you don’t need 5 pairs of black skinny jeans, no matter how “different” the “detailing” of each pair is.  This type of thing is what gets you stuck in a boring rut.  Stop buying cardigans if you already have on in every colour of the rainbow.  Try new things!  One of the best piece of fashion advice I’ve received from my very chic and dear friend Albert Chen is, don’t buy something that people won’t notice it’s new.  Your friends are a good resource.