For some, a personal style isn’t something they’ve had to think about, or take much time or energy to craft. Some people just get it, and they got it at an early age. If you aren’t one of these people, you likely had at least one or two friends who were like this. You know who I’m talking about: the girl who showed up at school looking amazing and avant-garde in an outfit you never in a million years would have thought would look good.
Maybe you had a uniform in high school; if you didn’t, it was easy enough to follow the trends and squeak by feeling relatively with it. In college, if you weren’t into clothes, or simply didn’t know where to start, you could blend in perfectly well with jeans, a school sweatshirt, and a ponytail. And, just think of all the professions that allow you to avoid choosing a style: working from home (jammies), police, medical, or emergency professions (uniforms), generic office work (unofficial “uniform” of dress pants, blazers, button-downs). Many offices also have a restrictive dress code that many find restricting but others may find to be somewhat of a relief.
The ability to externally express oneself doesn’t come naturally to everyone, and the advice out there for finding your personal style is frustrating in its assumption that this is an easy task. As you can see, those of us (yes, I am picking a side) who aren’t born self-stylists are able to coast pretty well without really having to develop this skill. That’s what makes it so challenging to start working on it later in life. (Say, in your late twenties.) Just as it’s harder to learn how to ski or pick up a new language the older you get, trying to cultivate a personal style can feel awkward, foreign, or just plain forced.
While I don’t have any earth-shattering advice, it was simple and easy enough for me. And it worked. My friends pretty much threw a little party the first time I showed up in a pair of moderately stylish boots last year. I got two offers to go shopping with friends who were thrilled to see that I was taking an interest in fashion. All over a pair of boots that I bought for $20 at Payless.
As incredibly stupid, obvious, and dorky-sounding it is, what worked for me when I took my first baby step was making a short list of celebrities off the top of my head that I
thought dressed well. I tried to avoid the over-styled celebs that you know don’t pick out any of their own clothes. When I looked at my list, I realized they were relatively minor celebrities, and more than half of them were British. A few clicks through Google images and Getty showed me that I seem to favor a kind of tweedy look that is exactly as nerdy as it sounds. But it was a start! This short little exercise led me to buy those boots, which gave me the confidence I needed to keep trying new things.
Rule number two is to forget designers. This may be a horrifying thought to stylish folk, but for those of us just starting out it is a waste of money and energy to get wrapped up in the intimidating world of designers. You could go to a store like Forever 21 that makes trendy clothes for cheap. You could shop online at discount sites to get the brands you want for a lower price. You could go to nice but mid-level stores like JCrew, Banana Republic, and the like. They’re just expensive enough to make you feel like you’re treating yourself, but they’ll never charge you thousands of dollars for a purse that their PR people forced upon the world. As long as the clothes are made well enough for your needs, and they make you feel pretty, then buy them.
Next, take a look at your closet (and, if you live in a tiny place like I do, your under-bed storage bins as well). What worn out sweaters, ill-fitting pants, or outdated shoes and accessories have you been holding on to? And more importantly, why? Everyone needs to keep those comfy, Sunday-afternoon who-gives-a-crap outfits, but if that’s your rationale for keeping every frumpy clothing item you’re going to still have a closet full of unstylish clothes. I did this for years, but was finally able to whittle down my chunky sweaters and corduroy pants to a much smaller, more manageable number. And, while I hope it goes without saying, you should donate all clothing that isn’t stained or damaged to the Salvation Army or similar thrift store.
My only other word of wisdom is to just dive in. I was intimidated by clothes and accessories, and I remain somewhat so, but I was able to at least take a bit of the fear out of the whole process by just taking a deep breath and trying out a few things. You’ll make mistakes; I bought a pair of patterned tights last year that not only look horrible, but don’t match anything I own. Thankfully they were on sale so I didn’t sink too much money into them. But you’ll also make some great discoveries. Mine? I love boots, and there are lots of cute blazers out there that won’t make me look like the principal from Ferris Bueller. Not that there’s anything wrong with that.