Switching gears, briefly: Let's talk about fashion! Personal Stylist: Part I

This is the first in a series of posts that I'm going to do about Outsourcing for Women: Personal Stylist. There's a very successful entrepreneur/writer/blogger named Tim Ferris who wrote The Four Hour Work Week. I've heard a lot about it and people tend to love it for its imaginative and efficient way at dealing with standard work problems that make you work longer than you would actually need to.

I've been interested in the idea of optimizing and making your leisure activities faster. And so begins my investigations into Outsourcing for Women, or The 1 Hour Errand Week, or something else To Be Determined. Anyways, I've started thinking about where my time and energy goes and how to optimize and streamline that so I can do more of what I love and be happier in my day-to-day life. I realized stressing about what to wear/not liking my clothes takes a lot of my time and also brings me down not all the time, but enough to make me think that there's something I can do to stop bringing that on.

And so here begins my multiple part piece on the Personal Stylist.

Cost: $125/hour

Yup, it’s expensive. When I first saw that number I balked and thought, “I don’t have the money for that!” But, bear with me. I’m going to give myself away and let you know that I’m going to argue that it’s worth it and less expensive in the long haul. But, I have lots of words and data to back that up, so stay with me.

I am also going to argue that it makes your wardrobe much more enjoyable! I hated shopping for the longest time and had had many frustrating experiences.

Here is a recap of the frustrating experiences: I often would procrastinate work or distract myself from boredom through online shopping. (Anyone else been there?) It might start out as a browsing trip, but would quickly turn into a hunt. I’d identify something that I was sure I was needing, like soft tee shirts that didn’t look stretched out and baggy from years of wear. But, it was so hard to find something online for the price I wanted, so I’d end up going cheap on myself, or forcing myself to get something from a retailer that offered free shipping and free returns. Much of the time once the item got home, I wouldn’t like it or it wouldn’t fit well. I was constantly cheaping out on myself, but didn’t trust myself to make sound choices in my shopping. I was insecure and that insecurity motivated me to get the cheapest option, which I was ultimately disappointed by. And then my closet ended up being packed with cheap, “fast fashion” that was gratifying in the moment of the purchase, but a few weeks and washes later, was disappointing and ill-fitting. And this didn’t just happen in online shopping bouts – it happened when I went to the mall, too. I just didn’t have the confidence to pick out what I wanted and didn’t feel like I really knew what was worth spending money on, knowing I would wear it for years to come.

And these are the most recent experiences. That doesn’t even touch on the years of being dissatisfied with my body and picking unflattering items off the rack, then blaming myself for not fitting into it or wearing it well. I would see the piece of clothing as the standard, and myself as at fault for not wearing it well. Nevermind the idea that the clothing was at fault, or simply that it wasn’t the best look for me. I would take it all very personally and come home empty-handed or worse, carrying things I didn’t really love.

So, finally frustrated enough to give up doing it all on my own, I searched online and found a local stylist with a blog I really enjoyed. She didn’t promote an unrelatable, unapproachable style of fashion. She had examples of outfits on her website and they ranged in terms of occasion and preference. I thought she had enough flexibility and expertise to help me find a unified look.

Now, before you get all judgey on me, let’s talk about fashion. I’ve rolled my eyes at it for a long time, thought I was better than those people who spent time talking and fussing over clothes. First of all, I apologize to all whom I’ve silently judged before – and maybe not so silently. Your interests and your pastimes are none of my business. Second of all, I was wrong. Whether or not you’re trying to, what you put on your body speaks about you. If you are really anti-fashion and dress in the same clothes you bought from K-Mart in 1993, then you are communicating that you really don’t care about fashion. Or you’re communicating that you’re overworked or overwrought or something else. People judge each other based on appearances, so to say you are above that is simply incorrect. Your physical appearance is the first thing others see and categorize you by, and this is plain and simple cognitive science.

To quote a fashion designer interviewed in the book, Paris Street Style: A Guide to Effortless Chic, Christophe Lemaire, “Clothes are the surest vehicle of self-expression available to us. To dress oneself is not futile – it is an act of profound significance. I believe in a style that expresses the inner self, that is neither a shell nor a disguise for it. To wear clothes is to be oneself, to dream oneself, to be aware of who one is. Dressing allows us to sublimate ourselves and to have fun doing so.”

I think that’s a pretty positive perspective on dressing. There’s no need to spend a fortune on your wardrobe, and if you’re chasing labels and brands to inflate a low self-worth, no amount of shopping is going to make you feel confident. And it's not about being trendy or forcing yourself into someone else's idea of what's good or pretty or acceptable. It's about deciding how you want to exist and be in the world. It's about deciding on the beauty that you want to experience through your own body. And that's what I wanted to cultivate. I wanted to feel confident, beautiful, relatable and, yet, graceful – a delicate balance that I thought an expert might help me achieve.

My stylist offered a range of services: closet purge, online shopping, in-store shopping, “shop and drop” (she shops for you, you try on by yourself, give back what you don’t want), going to the tailor with you, outfit formation, and present shopping. Her website offered all sorts of referrals to local professionals she recommended such as a great tailor, hair stylist, and make-up artist.

I was ready to book. I was feeling overly extravagant and nervous about spending all this money on myself, but I’d had enough of feeling shlumpy when I looked in the mirror. Plus I had a history of being pretty frugal, which meant I had a good amount in my savings account... it was worth a shot.

To be continued...