I never wake up feeling the same way each morning. Some mornings, I’m like a sloth, blinking open my eyes and wanting to crawl back under the covers for an undetermined amount of time.

Other mornings (and this might count for 1x a month) I wake up before my children to a quiet house. But never greet the arrival of dawn with excitement or anticipation. Mornings are a bit of a battle and when someone tells me they like to exercise before 7am I feel a bit sick. But something has made mornings a little easier for me.

It started a few years ago with a pair of brown leather boots I bought at Boxing Day sale. That was the beginning of a love affair with clothes and all the ways I could express myself to the world (now pictured below with my fun bo-ho hat). I wore this to a hippy costume party and love ALL the elements!

Since then, I’ve acquired a goodly number of faux leather jackets, (and to my husband’s dismay a few real ones), a wide assortment of black shoes and the best collection of clothes I’ve ever had in my life. The best part is I love following fashion, but also keeping things timeless. I love the look of Jackie Kennedy but also love being a rock star with skinny jeans and sheer blouses.

Everyone always writes about having 5 critical items that work for dressing for any occasion. I think that’s the silliest thing I’ve ever heard. How can everyone have the same 5 pieces? Everyone has a different body shape and especially a different soul. We should buy and wear what makes our feel our best selves. Regardless of what “experts” say.

I think it’s all about a feeling. Sometimes I feel like I can pull off wearing a powder pink turtleneck with powder pink pants and beige wedges. Other times, its faux leather pants with a black sweater. The thing is that clothes are meant to be fun and being able to express yourself by letting yourself look silly is just a part of the process. The end result is not to look silly, but to dress with a sense of fun. Life is short. Get the boots that make you feel like a million bucks. But don’t spend a million doing it, or anywhere close. Shop the sale racks at all costs!

Trying this or that and trusting that feeling of “yes” when something looks good is the key to looking your best. The other essential part of the process is constantly reviewing what you have and if you don’t feel good in something then pass it along to someone else. I read a great book this summer called the “Life Changing Magic of Tidying Up.” Now everything in my possession, especially in my wardrobe, is something that I think is cool.

I’ve switched from gardening magazines to Vogue and it feels great to experiment a little with clothes. Yesterday, I bought the silliest pair of raspberry colored leather wedges. Here they are! I am in love. And that just feels good.