The “Purposeful Style” Challenge 

The “Purposeful Style” Challenge 

Are you a boss? Do you NEED to dress like a boss? If so, then this article is for you and I invite you to a “purposeful style” challenge.

The term has been coined by Jessica Brown who is absolutely immersed in purpose at her job at the XPrize Foundation.  Jessica and I were talking the other day (I am a Visioneer for XPrize this year) and she asked me to write this article and share with the world my style process and personal philosophy.

You know the saying: “dress for the job you want, not for the job you have”? I totally agree with that. I am Romanian,  and Romanians have a different saying: “the clothes don’t make the person”.  While philosophically I subscribe to the depth of that sentiment, I feel in my bones, and know pragmatically, that the saying is wrong and that the clothes, often, absolutely, do make the person…

Clothes are like the packaging on the product. Think about it for a second: would you buy 100% of the things you buy if they would come without a package? If you wouldn’t be able to understand the value the product can bring to your life just by looking at its box? If you wouldn’t be able to extract the top 3 features just by glancing at it, by absorbing the FEEL, the essence of the product through the color and texture and shape of the presentation? This is what branding is all about, and well designed brands live this to the core, articulating who they are and what they are about.

I don’t care if you work for yourself, work for someone else, or don’t work at all. You need to be your own brand and embody that in everything, from your socks to the pen you write with.

In this world, a product without a package speaks about itself: that it is handmade, or perhaps used, or open box, etc. Even the absence of something means something and it’s the same with clothes. Don’t believe that just because “this” (whatever “this” is) is not important to you, it’s not important to others. Your clothes speak volumes no matter what. There is always a message there, and the simple point I am trying to make is that you should, absolutely should, make sure that a). You know what is the message you are broadcasting, and b). You broadcast a message that is consistent with your goals. For bonus points, I hope that you create a system that makes putting the “packaging” on every morning both easy and automatic so you don’t need to agonize each day over “what am I going to wear today?”

I could venture a guess that this is easier for men than for women, but if I look at my husband’s collection of 100+ pristine dress shirts I know this is not just a women’s issue. Out of these 100+ shirts, he probably currently resonates with maybe 20; if that. There is nothing wrong with the rest, and they still fit, but he is no longer the guy that bought those shirts… And don’t get me started on his slacks collection. Alas.

Back to the deeper significance of our packaging. How many books would you pick up and read if they would all come naked, without a title that would tell you what the book is about, without a cover that would communicate which category you should mentally place that book in? Yes, covers could be misleading, but a world with no book covers would be unimaginable.

We know all these things about products instinctively, yet, when it comes to ourselves we forget that our skill-sets are products that we need to sell, and  that most people can’t tell at first glance who we are, what we are about, and how might we go through life applying that which we know.

Believe it or not, our clothes can say that about ourselves before we even open our mouths. Additionally, clothes and accessories are icebreakers: how many times have you had conversations with total strangers because of something one of you holds or wears? Countless times, I am certain.

My clothes and accessories are like my websites: they have to say the right message and sell my skill-sets while I am busy doing other things. And here is where attention to details + intent + thoughtful curation are paramount.

With being Romanian also comes a fair degree of vanity, I will say that to get it out of the way. As such, it has always been important to me to broadcast certain things about myself through the power of the material possessions I own and carry around: that I believe in beauty; that I believe in style; that I am successful without being a total snob; that I like technology without being ruled by it; that I am practical, efficient and that I like clever things… Second to the messaging, such objects need to be close to zero maintenance. If something is high maintenance, I don’t care how cool you are, you gotta go. It’s not even a conscious decision anymore; it just IS.

Back to clothes.  I have always been into fashion and I like paying attention to the way I look when I walk out the door. It is both a sign of respect towards myself and respect towards the person I am meeting with. Plus, no matter how much we are trying, we can’t separate the clothes from the person. It screams something loudly, so we might as well pay attention to it.

Buying clothes is hard work. Who says otherwise is seriously confused and/or has never walked out of a fitting room depressed, with scratches on the face, a broken nail and the hair all over in a mess, possibly all of the above in one session. Buying clothes takes not just money, but time, intent, objectivity. It is also pretty fatiguing at the physical level which can affect one’s objectivity, so I have put a framework in place to help me.

Rule Number 1: My most important purchasing rule is this “every MAYBE is a NO”. By that I mean, if it doesn’t scream “F yeah, you look amazing and I wouldn’t change a darn thing about this!” when you put it on, it doesn’t get purchased. If you do nothing else, incorporate THIS rule.

Rule Number 2: shop alone. People are too nice and they don’t want to hurt your feelings.  If you shop with a friend you’ll end up with shitty purchases. Who is going to have the tact, skill and convergence of vision to guide you? Nobody, unless you hire a superstar a-hole stylist who will give it to you straight, which if you can afford, do.

Rule Number 3: If it doesn’t fit perfectly – and by that, I mean PERFECTLY and supremely comfortably – it doesn’t get purchased. I can hear you argue: “but, but, I can tailor it…” Of course you could. Why spend the time and the money though? Plus, there is no guarantee that after tailoring the piece it would look the way it should. Plus, do you really want to stare at this thing to and from the tailor, on your passenger seat or your To Do list for a month? Too many clothes in this world, too little time. If it doesn’t fit PERFECTLY of the shelf, walk away. Walk away!

Rule Number 4: stay both inside and outside of your comfort zone. What do I mean by that?

a). You already know this or that about yourself and your body; don’t reinvent the wheel because it’s not going to be any rounder the second time. For example, belted dresses will always end unworn for me no matter what delusions I might entertain at any given moment. And no matter how many silky, smooth, luxurious ties I might buy as gifts for my husband, he still hates ties with passion. Not buying that stuff means knowing where the comfort zone is.

b). Do try on different kind of outfits and more unusual combinations – your next “totally you” look will always be at the edge of what you are doing right bow.

Rule Number 5: know that who we are changes with time. We go through phases, the body changes, our life changes and the clothes we own are suddenly not right anymore. If we are lucky, we notice and do something about it. Pay attention. Don’t buy what you used to buy just because you used to buy it.

Rule Number 6: remember that you vote with your money. Slave labor is still rampant and clothes manufacturing is a top offender in this area and in pollution. Cheap fashion is made by oppressed people in unhealthy environments. Nowadays I buy very few things from brands I know something about… Less is absolutely more and yes, it means paying more and buying less often. I am OK with that. Be educated and be informed, and let’s use things to the end of their natural life – let’s go back to mending, and polishing leather, and taking care of high quality items, let’s only own beautiful things, great things I wouldn’t mind passing onto my daughter.

Clothes are also a harmonic duet with the rest of us: hair, skin, level of activity. I decided about 7 years ago that I won’t dye the white hair that has been sprouting with ferocious rapidity. Because the work that I do often involves conversations about millions of dollars, I feel that the white hair is a). A manifestation of the wisdom and expertise I possess on the inside, and b). A badge of honor speaking volumes about rites of passage from the tribulations of life. I earned every single one of those darn white hairs! Of course, the emergence of white hair means my clothes have to match that. And no, plastic earrings and cheaply made stuff is no longer an option. It’s cute when you are 16. When you have a few white hairs, you have to know that what worked a while back will never work again.

For years I have been embarking on twice yearly purges of my closet. If it doesn’t fit or if I haven’t worn it in a year, off it goes! I don’t care if I paid a little for it or a lot. Either I have a clothes-swapping party with my friends or I send it to Goodwill and feel good about it, knowing each piece has a second chance.

Everything in my closet is hanging on white hangers, by category and by color. Bags and hats are on hooks so they keep their shape, shoes are out of boxes because if they are in a box I forget about them, and for the rest I use baskets and drawers (one for socks, one for PJs, one for workout stuff, one for travel and specialty clothes, etc.) I have a bit of a scarf addiction, and possibly a coat problem, so keeping an eye on this insures that it doesn’t get out of control. Jewelry is in compartmentalized containers and 2-3 times a year I rotate batches because otherwise I will wear the same earrings every day for a year.

This is simply my system and it is rooted in a deep understanding of who I am, who I am not, and what works for me. I am NOT Heidi Klum; I am a petite woman, built like a tank and with a life that resembles a military operation. My days as an entrepreneur start at 6:00 am and often end at 2:00 am with merciless transitions from facilitating board meetings to school pickup, and possibly naps and/or evening events. Whatever I wear has to have a cross-functional slant.

This system is also based on a vow of renunciation: I gave up on fantasy life, I gave up on the belief that one day I will have more time, be a teenager again or be 50 lbs lighter. I am sharing those things to inspire YOU to think in detail about who you are.

For the longest time I had a policy of “1 item in, 1 item out” which keeps crazy impulse shopping to a minimum because you know you’ll have to get rid of 3 favorite items if you just bought 3. So it’s been pretty fierce.

Is this for everyone? Perhaps not, but give it a go.

This year I took this to a whole new level because I wanted not just to look good. That wasn’t enough anymore. I wanted my clothes to speak truth to power and say the story of who I have become.

That wasn’t easy because first, I needed to articulate all that in my head, and then translate it into a visual representation.

Who I am? Entrepreneur, field revolutionary, wise woman with an edge, lover of classic lines, and unfussy frequent traveler, mother and wife, a person that has seen the world (and a thing or two). Now, how do you translate that into fashion?

One afternoon, after a lunch conversation about fashion, decision-making and lifestyle with the amazing designer Jenisa Washington, it became crystal clear. I knew exactly what the right wardrobe for me should look like: in-your-face, highly stylized; a bit geometric, clean lines without embellishments. High end fabrics without being precious. Timeless with an edge. Precise. Structural. Lots of black leather accents, which I decided is my signature touch.

I went straight from the restaurant to my favorite store and bought a handful of pieces I was missing. The pure alignment of object and vision was reflected in the price tag: I spent on those few pieces twice the Blue Book value of my first car; no regrets. Then I went home and emptied the closet completely, tried everything on, and then I put back in the closet only the very few pieces that fit the vision.

After 10 hours of intense work, I trimmed my wardrobe to close to 30 items, and that includes winter coats and a few statement pieces. I eliminated a whole section and I pared down shoes and purses too. All in all I kept less than 20% of what I owned; the other 80% went to Goodwill.

Next day, I spent another 8 hrs or so creating outfits, cleaning my accessories and making sure my lipsticks and everything else complements and completes it all.

Exhausting? You bet. Exhilarating? Absolutely.

When I was done, my closet revealed space previously lost in a sea of unusefulness.

I had one rack of black clothes, white clothes, and a small number of grey/beige items. Pops of color come mostly from accessories, lipstick, nails, etc. Everything goes with everything. Everything has the same esthetic. When I purchase new items (which I plan to do extremely sparingly) it will be clear at a glance if the new item fits in with the rest, which in itself is HUGE.

I don’t have a plan to do this again anytime soon, and I know that because I took the time and put the effort in, I won’t have to.

Now, I don’t need to think too much before getting out the door. Packing for a trip is a breeze too. My closet is a joy to walk into, and my wardrobe looks not just good, but it looks like ME; who I am, who I have become and what I am about in the world.

So I am asking you: what’s your purpose and more importantly, what’s your purposeful style?

Try this approach. It’s worth it, and I guarantee you will love yourself and your own life, and if you do this full on, you will become better positioned in the marketplace, make more money, and become more confident (which is why you’ll make more money).

I challenge you!


Cristina Gallegos


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