Many of my clients hire me for one primary reason – to help them move out of their style comfort zone. They are bored with their current style and it’s time to change things up. Sometimes the changes are drastic, and sometimes they are subtle. Either way, I love helping people transition into new ways of presenting themselves to the world. Their journeys are always interesting, reflective, a learning curve and full of surprising aha moments.

One of the surprises: The hardest part isn’t figuring out the new style, or even purchasing all the items and creating the ensembles. It is making the change and actually wearing those ensembles. The thing is that most people are fairly resistant to change. Even though they have decided to evolve their style, and are paying me to help them do so, it ends up being harder to embrace the change than they ever expected. It’s my job to make the transition as fun and painless as possible.

When I help clients move out of their style comfort zone, I start off by asking two big questions:

  1. What are your style aspirations, goals and expectations?
  2. Are you happy with your hairstyle?

The first question they expect, but the second often comes as a surprise. I ask it because I’ve found that a person’s hairstyle has a very dramatic effect on how they view their current and future style. By addressing a client’s hairstyle right from the start, things naturally fall into place. Often the new hairstyle alone makes my client’s style feel completely different. And sometimes it is exactly the impetus they needed to get out of their comfort zone.

After in-depth discussions and reflections (and frequently that all important trip to the hair salon), my client and I start working towards achieving her desired new look. We review and edit her closet, create outfits with existing wardrobe items, shop for missing pieces and build a range of lifestyle appropriate ensembles. This style renewal process takes time and we often spread it out over several months.

During the process, my client has one important piece of homework: To road-test her new style as soon as possible.

This is when we get to the crux of moving out of the comfort zone. Even with all the right wardrobe items in place, a cheat sheet of dressing formulas, photos on how to put the new looks together, and all the encouragement in the world – it can still be challenging to put a new personal style into practice, especially when the changes are drastic.

I can only take them so far. THEY have to do the rest.

At this stage, I offer two alternatives for how they can move forward with the transition:

  1. Throw yourself in the deep end: Pick a new look outfit from our styling sessions, put it on and head out the door without thinking too much about it. Just do it. Expect to feel a little weird at first and expect outfit commentary from others. Do the same thing the next day, and the next day because practice makes perfect. With a little perseverance, tenacity and motivation, your new style will feel more “normal” – both to you AND others.
  2. First dip in your toes, then your waist and then the rest of your body: Break in your new style slowly. Mix aspects of your old style with aspects of your new style. Take an item that’s out of your comfort zone and wear it with a few trusty old wardrobe friends. Eventually you’ll work your way up to your new personal style. I spend A LOT of time helping clients to incorporate their new looks slowly but surely, holding their hand as much as I can.

Often people use both of these strategies as they move out of their comfort zone. For example, when I wanted to wear gold metal, I threw myself in the deep end. I walked out the door in gold accessories and hardware one day and that was that. I did it again the next day and the day after that, and soon it felt like me. But when I incorporated skinny jeans back into my wardrobe in 2006, I had to break in the look slowly. I first wore them with long tops and boots. As I got more confident I sported them with short layered tops, jackets and boots. I had to work my way up to wearing them with blouses and flats. In a couple of months, putting on skinny jeans felt every bit as natural as putting on a pair of bootcuts.

I’m sure you’ve moved out of your comfort zone at various points in your style journey. Do these transitional strategies sound familiar? Care to share examples of how you moved out of your style comfort zone? Were your strategies successful? And what did you learn along the way?