In order to really see what you are working with, you need to take inventory and decide what to do with each item. As you look at each garment, decide whether you want to keep it, get rid of it, alter it, or mend it. This doesn't have to be a chore; it's rather exciting to rediscover things you haven't worn in ten years. Or even two. The trick is, to approach it with humor and a damn good sense of fun. Making a party out of a funeral is at the core of this stage in lifting your Style Strategy to the level of where it should be.
Clean your closet a la "Sex and the City," the movie. You know, the scene where Carrie Bradshaw is getting ready to move in with "Big" and tries on all of her clothes for Miranda, Charlotte and Samantha? Experience your own montage. Invite your girlfriends over to help with the editing. It might even be fun to take pictures for reference and nostalgia. Give yourself at least an afternoon because there will be a lot of reminiscing involved (both great and horrendous). Have some cocktails -- but not too many, this does require that you be fairly lucid. Then you can return the favor for each of your friends. Make it a rotating, seasonal party. A very close friend of mine, who I have always admired for her ability to make a good time out of any situation, once told me that giving a "theme" to any gathering instantly makes it a million times better. So, theme it up. Throw a Catwalk Party, for instance, and get set to laugh and cry as you pave the way for renovation.
Go through everything you deem worthy of keeping, piece by piece. Check very carefully for stains and holes. Start thinking about what different things would look good together. If you have a dress made out of a gorgeous silk, that you absolutely love, but has just never worked with anything else that you own, try to imagine what would make it work. Can it be altered? Would it be more versatile as a skirt? Would it be more flattering without pockets? As a sleeveless shift? Belted? Just reviewing everything you own, in its entirety, will give you a million ideas for updating your look with what's already in your closet. And, as I said in The Little Black Book of Style, your tailor should be one of your best friends.
It is really quite delightful to give your old clothes a new life. By reacquainting yourself with your wardrobe, really studying it, and using your imagination, you will be amazed at how many more outfits you have than you thought. By analyzing garments and picturing how they would look with different pockets, or accessories, or trim, you're learning to be your own designer. And you're learning to appreciate good design. You will be personally, not just financially, invested in your clothes. You're training yourself to pay attention to how things are constructed and what they're made of, which will make you a smarter shopper. And this training carries over into other aspects of your life, too. It's an excellent way to exercise your critical thinking and creativity. Who said fashion is frivolous?
Try things on. Attempt to look at each item in a new way. See if you can identify how pieces could be improved or worn differently. You will develop a better understanding of what looks good on you, what you like, and how you want to present yourself. In other words, you will begin to understand your personal style! And once you understand that, you will project it to the world with a new confidence.