It’s Not Easy to Change Your Style. That’s OK, You Can Sneak Up on It.

It’s Not Easy to Change Your Style. That’s OK, You Can Sneak Up on It.

Most fashionistas, stylists, and their “listicle” blogs say it’s simple to change your style. “Just experiment!” they say. "Get some new shoes! Try new prints!" They make changing your style sound like it’s as easy as painting your bathroom over the weekend. If only it were that easy. They forget that for many of us, changing our look is a scary thing to do. Our very identity can be powerfully tied to how we dress and wearing something that is radically out of character can feel like we're the only one wearing a Halloween costume at an important dinner party. If you're like me, you need more than just a shopping list to really start changing your look. You need to get over the fear of it.  I’ve found a fun way to build a bridge between you and a new look and tell fear to take a hike: Wear a wig.

Style doesn’t start with your body. It starts with your Brain.
— Stacy London, The Truth About Style

To me, style was always mysterious and difficult. So many emotions were wrapped up in it. Wanting to belong, but wanting to look unique, and then being forced to look “unique” anyway because I just couldn’t wear what most girls were wearing. 

Starting with my first job out of college at a downtown San Francisco law firm, and continuing until just a few years ago, I thought about how I dressed only in terms of the image I wanted to convey for my job: competent, conservative, dependable, classic. Work wear was my priority. And let’s face it: a classic suit that fits, on a man or woman, has always looked good in the professional services world. Since I hated shopping for clothes anyway, having a go-to look was both practical and easy. 

It was all about clothes shopping for my career and livelihood, with much less emphasis on shopping for the important things like weekend barbecues; you know, clothes shopping for a full life.

All Work and No Play.

After years of working too much and caring more about my professional wardrobe than a wardrobe for anything else, I realized I was in a long-term style rut. It was all about clothes shopping for my career and livelihood, with much less emphasis on shopping for important things like outfits for a night out or weekend barbecues; you know, clothes shopping for a full life. The conservative, relatively plain look I chose for work became my “style” and it influenced the choices I made for my non-work style too. I soon convinced myself that other styles wouldn’t work, didn’t look good on me, or simply "weren't me". In truth, I was probably just hiding underneath that plain, dark wardrobe, trying to fit in by not calling too much attention to myself with my clothes.

Style isn’t something stagnant. Like us, it’s always in flux. It’s a valuable exercise to reassess your style, to see if it reflects where you are in your life and not some old notion of who you were.
— Stacy London, The Truth About Style

Community and Wigs.

Then I moved back to the Pacific Northwest after several years in Texas. Escaping the Houston humidity was only part of the reason I moved to Portland, Oregon. I also came because I wanted to be closer to family and become part of a community. In Portland, I have been exceptionally fortunate to have found a group of smart, talented, kind and fun women friends. They are the heart of the larger community I was looking for and they welcomed me into their raucously fun circle.  

Our group has many fabulous traditions, but one of them in particular has been life-changing for me. It has helped me to do the brave thing when faced with the choice between trying out a new style and slinking back into the boring safety of a style that no longer fits what I want in life. That tradition is Wig & Wine Night.

What is Wig & Wine Night?

Here’s how we roll. On a Saturday afternoon, we show up at our favorite wig store for inspiration and a wig (for us, it’s Wigland, on NE Broadway in Portland, OR). We begin our hunts for a new alter ego for the evening. Always wanted to be a redhead? Why not? Want to see what the world looks like as a platinum blonde? Go ahead! It’s a little bit of the Halloween costume vibe, but without those stupid, sexy nurse outfits. Often we don’t buy anything new, we just swap the wigs we have..

What next? We go home and style ourselves to fit our new wigs for a hilarious evening; we get to be someone who looks completely different, but at the same time, still looks a lot like ourselves. 

The Big Reveal.

My first time at Wig and Wine night, I was full of nervous excitement. I had chosen a radically different look. I’m a redhead with a face full of freckles. I always have been. Here’s how I looked back then. Serious. Career focused. ZZzzzzzzz…..

All about work....

All about work....

But I really wanted to see what life would be like as a blonde, so I found my first wig. And not only was it blonde, it was long and the hair was straight - absolutely nothing like my own hair. Then I picked out something from my closet I had bought because I loved, but hadn't had the nerve to wear yet: a leopard-print knit skirt. That night I wore it with a slightly fitted dark brown turtleneck and those tall leather boots you already know about. This outfit was nothing like I would ever wear. It felt too clingy (though it really wasn't) and I had this idea that leopard print was just somehow, I don't know, racy. It was all so out of character! But that was exactly the point.

My first Wig & Wine: Blonde life.

My first Wig & Wine: Blonde life.

I know what you might be thinking: Are you kidding me??? That’s a photo of someone going out on a fashion limb??? Hell, leopard print is practically a neutral!!

For me, it was super scary. And hard.  


I laugh now at how uncomfortable I was to wear that outfit that night. But my friends loved it, and they told me so.  “You should wear that more often!” they admonished. It turns out that I just needed some way to get comfortable with a totally new look. The wig night was just a few years ago, but experiencing how that look felt in a safe, near-real life situation was an important one. A couple of years later I had even worn that exact ensemble (without the wig!) to the office several times. I didn't even think twice about it.

Another Wigs & Wine: Blondes have gone brunette and red, the brunettes have gone red and blonde, the redhead has gone blonde again. Here, I'm in the front row, taking a scary new red dress out for the first time. 

Another Wigs & Wine: Blondes have gone brunette and red, the brunettes have gone red and blonde, the redhead has gone blonde again. Here, I'm in the front row, taking a scary new red dress out for the first time. 


We’ve had more Wig & Wine nights over the years and I’ve used them to experiment with other new looks too. For example, the edgy, pleather moto-jacket with the fake fur that reminds me of a gorilla?  (My friend swore I had to buy it at a Dress for Success Acey’s Closet Sale last year but I felt absolutely ridiculous in it). The jacket went out on wig night with a spiky, purple-streaked black wig, spiky shoes and a sequined tank top. Yikes! But again, the ladies all gave me the thumbs up.  

 

They gave me a thumb's up for this look too.

They gave me a thumb's up for this look too.

The jacket turned out to be really awesome. It just needed a wig night to give the look a good test run first. I’ve even worn that jacket during the day since then (shocking, I know).

There’s absolutely no shame in being afraid to change your style. It's normal. It really is hard to part with who we've been on the outside. They call it a "comfort zone" for a reason!  But it can be fun to embrace an outside expression of the person we are becoming inside, as we realize we've moved on. And sometimes we're just bored with that old look. We need only notice how popular Halloween is to accept that we all have a desire to change our image once in a while. We just need the permission.

Give Yourself Permission.

So give yourself permission and create your own excuse to experiment with a group of friends. You might feel ridiculous going out wearing a wig at first, but after you’ve had a couple of cocktails and a lovely dinner, I promise you, you won’t care. Put on that dress you bought because you loved it but are now too chicken to wear! If it’s too scary to go out in public with a wig on, have a dinner party at home with your girlfriends and start there. I’ll bet you’ll decide to bail on staying home once you see how much fun it is though. I look forward to seeing you out there!

Clarissa Cooper of Portland OR is the founder of WeFitMe, an online community of like-bodied women helping each other find clothes that fit. Clarissa has over 30 years of experience in the women’s apparel industry as a CONSUMER, as well as a background in finance in the energy industry.

Header Image: Getty Images

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