I have learned a LOT being a YLF forum member for more than 3 years, but my closet doesn't really reflect that. I can quite happily tell everyone else what to do, but I don't seem to be able to practice what I know and have learned.

I'm unhappy with my collection of boring clothes. In striving to cut back on wasteful purchases, and to keep a tighter closet, I have sucked all of the fun out of my closet. I also am not interested in fast-fashion , or buying from those whose retail and manufacturing processes are environmentally and socially unacceptable (H&M, etc ) and being trend-carzy is not appealing either .

Now, it's not like I had a wardrobe full of colour and print, with a variety of silhouettes, but I did have a LOT more clothing . I have many nice , high-quality things, but they are all versions of one another. The breaking point happened yesterday , when out for some leisurely browsing combined with a sales call along one of our best boutique streets, I stopped in to a favourite shop to look for a pullover sweater . Black. (yes, sorry). The shop owner, who is a delightful girl of about 28 and who knows me fairly well, looked me up and down (in my all-black sweater and jeans outfit) and announced that there were a few black sweaters, "but you know, we specifically bought fall with a lot more variety and colour this year". Ouch. But looking at myself in the mirror in the hot fitting rooms while pulling sweaters over my head , I felt crappy and disheveled in my less-than-pristine black sweater (which I why I wanted a new one) , dull black jeans, and dull black sneakers. I wanted to slink out of there and go home. Anyways, this is all to say - I hate my clothes and hate my style (or lack thereof) and don't know how to approach what feels like a long over-due makeover.

I think my biggest roadblock is a lack of body confidence and a fear of looking silly or kooky. I stick to a very few silhouettes that provide coverage of certain parts of my body I care not to highlight . I'm way past the age of needing to feel constrained by fear of what other people think , or by my own insecurities - but somehow they still rule. I have become quite fascinated by a blogger I've followed for a couple of years - Shauna Robertson at Chicover50 - whom I share nothing with in terms of appearance except for perhaps the hair. Anyways, I often dismiss her look as too kooky and slightly off , but there is something very appealing about how happy and comfortable and interesting she looks . She's wedded to a few stores (Anthro primarily) so her look is influenced that way - but look at all of the colour, the fun , the everything ! Am I just envious of such a big wardrobe and a big budget?

How can I open my eyes to introduce more fun and interest to my style? Where does one start?