This is one of the most thought provoking threads I have read in a long time.

I hope that these thoughts have helped you, TG. They were very interesting to read.

FWIW, I think you can have a set of style descriptors that convey your style authentically all year round - and for a while. Modern, Simple, Clean, Bold and Dressy has worked well for me for three years and I see no need to change them unless they begin to feel off somehow. Having these adjectives in the back of my head as a frame of reference, has REALLY helped me focus when I purchase and put together my outfits. So personally, I've has success with the strategy. (High five, Astrid).

I echo what Janet said by a billion percent. For some, the analysis is fun up to a point. For others, the analysis is as fun as sporting their sense of style. People are different, and as long as we keep on having fun with fashion and style, finding the strategy that works for you is key. Setting yourself free after some restrictions makes is a great way of putting it.

Becoming more self-aware in all aspects of life is a beautiful thing - it benefits you and those you engage with. The older I get, the more self-aware I want to become. (I SHUDDER at how un-self-aware I was even as recently as back in my 30's). This is a journey that is interwoven with your personal style. The two feed off each other, which is why style is from the inside out.

So TG, that's my long ramble. But in short, you are on a deep journey to self-awareness in all aspects of your life - and it's a GREAT journey. xo

I think that to the extent and degree that something works for you, than it's helpful, but when it becomes limiting, I think it helps to rethink and possibly adjust. But it has to be self originating and what serves you. For me, it's been helpful to think in overall wardrobe goals, what I need in what numbers and what degree of casualness or dress. Where I have found myself in a situation similar to yours is working to apply what I've been learning in terms of body type, color and cohesion. It's been really helpful to define what is most likely to work for me in terms of silhouette and colors. However, in applying it to purchasing choices, I'm finding that I want to use that as a guideline to make it easier to know what is more likely to work as items together and on me, but if something also works but doesn't fit that criteria I don't want to discount it.
As a side note, in regard to what you mentioned in starting a small business. I am in a similar process now. In the U.S., the Small Business Administration has classes that explore what it entails to start a small business and can hook you up with mentors in your specific field. Not sure if they have something similar in Canada but perhaps you can check out resources that exist about starting a small business to help you in researching your choices. Best of luck!

I have been overly strict like this in the past too. I think it's part of liking to have control: if we have some style monikers, then we think we can make buying clothes more of a cut-and-dried process that doesn't involve the possibility of error. Or maybe we feel inside that our style is changing, and we are afraid to experiment with new styles in front of others. I know sometimes I limit my "fashion evolution" because I am afraid of what people around me will think.

I go through periods where I am drawn to different styles. I was extremely drawn to boho clothing when I started my style journey, and I bought quite a few pieces of it, but then I switched to a crisper style (although I still had my "boho days"). But now I find myself being drawn to that kind of clothing again, after I had decided that it was probably just a past "fling" and that I was basically done with it.

I have to really respect myself and listen carefully to what my innermost self is saying to me so that I can follow it with my style choices. I do believe that at least for me, fashion is a way of working out some internal issues.

Gwennie, thanks for your insights and the small business info - I will do some research around that in Canada!
Gigi - yes - I could have written that myself - it is absolutely a control issue for me, as well as the fear of making a mistake. It results in bad purchases and bad purging and frustration. Glad I am starting to see it for what it is, and to know I'm not alone!

Great post - lots of things to think about.

I am late to this thread but I have found it fascinating reading and much food for thought.

I've found a style descriptor helpful and not restricting in any negative sense. It was especially helpful to me earlier on, as I tried to focus beyond simple body type guidelines.

In my case the descriptor was actually more of a style persona, and for some reason this felt more dynamic and flexible to me than a set of adjectives.

Torontogirl, your thoughts sound familiar to me as well! I wonder if part of the reason I haven't been able to figure out a style descriptor is because, once I have one, I'm afraid I'd kind of get fixated on it and use it to narrow things down too much. Even without one, I think I can go a little overboard on applying what I've figured out about my style preferences. For example, just because I love warm, rich, dark reds and purples and they flatter me, does that mean they have to be my default choice in everything? Probably not, but seeing them as "my" colors sometimes makes it hard for me to see other colors that may work on me just as well.

I also do this with non-fashion things, kind of like you describe. Things like oral communication and organization have never been my strong points. But that doesn't mean they're skills I can't hold my own in when I really need to, and it's kind of selling myself short to just avoid circumstances where I might need to draw on them.

TG just wanted to pop back and say thank you for your kind words:) And you comment about finding your own way is so very true. Others can inspire but ultimately we have to work out what actually works for us. And as with all aspects of life, the journey is were we learn, so no, we don't want to rush it.

Great post TG! I don't think I really have a style descriptor per se, but I guess I do have some adjectives I try to remember when I'm looking at potential wardrobe acquisitions. Funny, but I've been focusing on shoes for quite some time, so most of my adjectives are related to shoe shopping. Easy, comfortable, casual, soft, modern, neutral - all come to mind. I don't like a "bold" color shoe so much (I've tried several in red, yellow, shiny metallic) and those aren't really my personal style I've learned. But I do want shoes that are at least considered "current" in style. And yes, maybe my idea of aging has something to do with that. I actually got rid of some shoes after seeing someone who I do not admire in a fashion way (or in a personality way) wearing the same shoes because from that point on I associated those darn shoes with that person! Not sure what lesson that taught me, other than the fact that we do associate certain styles with certain feelings and one of those feelings may be "age."

Regarding your desire to become an entrepreneur, that is a topic near and dear to my heart. I hope you will not limit yourself in that endeavor. Embrace your inner sales person. Sales, or the more appropriate and descriptive term "business development" is the key to success in any business. People often give "sales" or "salespeople" a bad rap in their mind. Don't fall into that trap. Be your own best sales person and you are halfway to success.