Reader Request: Stepping Outside Your Comfort Zone

Julia popped this into the suggestion box:

... something I've struggled with (and have started discussing on my blog) is stepping out of my comfort zone in front of coworkers. I'm fine with wearing something out of my typical style when I go out around town, or out for an evening, etc. But I really struggle with this on a day-to-day basis. I DO care what my coworkers think of my appearance and style, but I feel like I've long established my style here in the office/lab. I'm self conscious that if I try something too new and non-Julia that they will notice (most of them are women and in my experience women have been more perceptive to style/clothing than men have) and think I am trying too hard or trying to be something I'm not.

When your personal style is evolving - and for many of us, that evolution is constant - it can be difficult to gauge which outfits make you look like a fashion plate and which ones make you look like a poseur. Of course, any woman can successfully wear any garment if she has enough chutzpah to pull it off ... but sometimes your chutzpah reserves run low and you end up feeling deflated and sore thumb-y. Add an observant, curious, and/or judgmental environment to the mix and you've got to conquer one more layer of challenge. Not only do you have to prove to yourself that you look amazing in those silk drop-crotch pants, but you have to convince your office, classroom, or social circle? Yoiks.

Luckily, there are plenty of ways to ease into wearing some of the more trendy or unusual items you've been longing to wear. Gradual incorporation and careful deployment can smooth the transition from old style to new. And these methods will apply even if you're shifting from one relatively conservative look to another, but prefer not to look like you've been transformed overnight into a "new you."

The tips below are drawn from this older post, which also includes suggestions for achieving your dream style no matter your figure size/shape, budget, energy level, or amount of expertise. So if stepping outside your comfort zone isn't your transitional challenge, take a peek at the other options!

Conservative/intolerant environment
You want to dress like a rock star, a pin-up girl, a circus performer, a mermaid. You want to do your hair big and wear monstrous combat boots and pile on bangles from wrist to elbow. Your parents or teachers or boss or office-mates or friends or lover will be scared/disappointed/angry if you do.

• Can you amass pieces and tools that contribute to your look, but deploy them in small enough amounts that it feels like your little secret?
  
  
• Can you learn to deflect biting comments by laughing with the commenter? "Hahaha, I know! Isn't this WILD?"
  
  
• Can you talk to a select few people about why dressing this way is important, so that you have some supporters amongst the dissenters?
  
  
• Can you dress down Monday, Wednesday, and Friday and dress up Tuesday and Thursday? Gradually get your environment used to what appears to be an experiment until the time is ripe for full transition.

Scared
You want to dress like Sarah Jessica Parker, Tilda Swinton, Sharon Stone. You want to break out of your rut, your shell, your feelings of boredom with how you look and dress and feel. But you don't know who you'll be if you do that, or if you'll still like yourself, or if you can pull it off. You don't want to be laughed at, or be disappointed in yourself.

• Can you be gradual about trying the new style? Make your bedroom the testing ground. Get up 20 minutes earlier each morning and just PLAY in front of the mirror. Make yourself branch out just once a week.
  
  
• Can you start by just wearing items from your coveted style around the house? Make sure you feel comfortable, love the look, have it honed so it feels like your own.
  
  
• Can you wear one or two signature pieces at a time? Don't go full-Carrie, just tack a giant flower to your blazer. Don't wear a wiggle dress and bright red lips and a string of pearls, just strap on your Minna Parikkas with your simple sheath.
  
  
• Can you take photos of yourself and look at them THE NEXT DAY? Get some distance and then evaluate. Learn how awesome you are one photo at a time until you feel ready to try out your new signature style in public.

Human beings react to change. It's natural for the people in your life to express curiosity about changes you're making to your appearance, because change is what keeps our lives interesting. Change your personal style, and you suddenly become WAY more interesting. Generally, people just want to know about your motivations. If you're changing how you look, there's a "why" behind it. But some people have trouble expressing their interest in a civilly inquisitive manner. Anyone who decides to criticize or attack you because of stylistic changes is really expressing anxiety about her or his own appearance, but that can be hard to keep in mind as you're facing down stares and whispers.

In my opinion, the best way to step outside your stylistic comfort zone is to do so gradually, and to arm yourself with ready verbal responses. Ease yourself and your environment into the change so it'll feel as organic as possible, but also prepare yourself for questions and comments. And stand strong. No matter what the response, you're making these changes for yourself. And that means they're worthwhile.

Anyone in the process of transitioning, and dealing with questions or judgment from peers? How are you handling it? Anyone have any other suggestions for ready-made responses to queries about stylistic changes? Feel like it's more effective to do the overnight change and let the dust settle in its own time?