How to Dress Like a Style Icon

Everyone has style. The ones who draw us in are those who know how to access style in a way that is unique to them but resonates with us. Of course, having good style is more than just wearing fashion. There’s an intangible quality about it that is hard to articulate but you know it when you see it.  Some have offered a definition of style. Amanda Brooks (in I ♥ Your Style) defines style as “a way of putting yourself together according to your mood and what you want to project”; Kate Betts (in Everyday Icon) says style is “bound up in who you are and what you believe”; and Jennifer Scott (in Madame Chic) says style is “what makes [you] feel good.” None of these definitions offer a wear-this-with-that approach to finding your style because there really isn’t one. And honestly if you had one, you aren’t guaranteed to project the authentic sense of style you’re looking for. Sure, you might look good in an outfit, but anyone with a stylist can do that. Having a sense of style is more than looking good in an outfit. It’s also about carrying yourself in a way that consistently brings out your best qualities.

I know I’m in the presence of good style when the following happens: my heart jumps a little in my chest, I end up staring for a little longer than I should, and I feel inspired to try something new. I’m drawn to people who have edited their outfit down to one stand-out thing— a must-have shoe, a really nice pant, or a cool piece of jewelry, especially if any of these intentionally throws the outfit in an unexpected direction. I’m also enthralled with people who aren’t necessarily wearing anything exciting but wear it in an interesting way; or who undeniably follow the trends and know how to rock it. While I can’t offer you a paint-by-numbers approach to how this is done, I can off you a few tips I’ve learned on how to develop your unique style. I've also included some virtual outfits to show you a glimpse of the way I put outfits together.

1.    Do Some Self-Introspection

Know Thyself

Any style icon knows who they are and what they’re on about on. If you haven’t quite figured that out yet, consider your goals and what image you want to project. What are you educational, vocational, and personal aspirations; and what image do you think best reflects those goals? I’m both a psychologist and a fashion/design consultant, and I love juxtaposition and blending different styles together. I tend to lean towards classic pieces mixed in with something unexpected.

Expose Yourself (and not in the way you think)

While you may have the potential to be a style icon, potential doesn’t necessarily translate into reality without knowledge and awareness. This involves actively searching out inspiration anywhere you can find it—museums, fashion shows, theatre, movies, magazines, and travel. Identify who you see as a style icon and why. Personally, I enjoy Solange, Choe Sevigny, and Miroslava Duma. I like their eclecticism and the way they’re able to transform their look to whatever is inspiring them at the moment while still staying true to their essence.

2.    Identify the Essence of Your Style

Cultivate “Your Way"

Whenever I have a difficult time articulating why I’m drawn to someone’s style, I say they have “a way.” It’s usually because I cannot pinpoint their sense of style to anything specific. It seems to be a complex mix of their outfit and accessories, their idiosyncrasies, and how they carry it all. While it may be easier for others to be aware of our "way” than it is for us, there are some things we can do to cultivate this elusive sensibility. One way to do it is to consider what aesthetic or look your drawn to, as it can give you a pretty good indication of what you already possess. Then use it as a guideline for how you shop and put together outfits. I’m drawn to the eclectic style of others because my style is eclectic. I like to call it “classic eclecticism” because it speaks to my love of adding an unexpected twist to classic outfits.

Identify What Pieces Suite Your Body

Even the most fabulous outfits will do nothing for you if you if it doesn’t complement your shape. As much as I love short shorts and rompers, I know it doesn’t flatter my legs and I look best in outfits that don't draw attention to it. If you’re not sure what clothing complements your shape, consider what you feel most comfortable in and why. When you’re trying on clothes in the store, walk around the dressing room in it to see if you can imagine yourself wearing it out. If you aren’t comfortable or are having problems with the fit in the store, chances are you won’t be comfortable in it when you get home.

3.    Know How to Adopt Trends

Know A Little About Where the Trends Come From

Often we adopt trends from sheer exposure without considering why we are drawn to them, how long they’ve been in the fashion cycle, and how it became trendy in the first place. There are a number of sociocultural, political, and historical factors that go into making a trend catch on, and it’s good to have at least some awareness of it so we can make an informed decision about whether or not we want to try it. In my experience, styles become trendy when differing styles have run its course; and there is usually some socio-political movement that supports the change. For instance, back in the 90’s, knee length skirts were all the rage, and it's becoming, minimalist shape seemed to be a reaction to all the decadence and “girls just want to have fun” vibe channeled by the 80’s min-skirt. As the economy has been on an upswing, the decadent 80’s have came around again, and we are embracing the unique, asymmetrical proportions we once enjoyed in the 80’s. Knowing this information about a trend can may help you decide if it is look you want to embrace.

Make Sure the Trend Feels Like You

I have no problem experimenting with clothing, but if it doesn’t feel like me, then I won’t wear it. What makes it feels like me? Well, I go by my reaction to it and the way I carry myself in the clothes. If I love it and can carry it with confidence then I know there is enough about it that is personal to me. For instance, fur/feather shoes were all the rage this season, and I was drawn to the edgy luxury of it after seeing a girl in Jersey City with a pair. She kind of had an attitude, and wore it so effortlessly that it looked like she just rolled out of bed with her fur slides. It made me want to by a pair, but I was very particular about which pair because I’ve also seen this trend go really wrong. So I made sure I bought ones that did not feel too over-the-top and complimented my foot.  If I try a trend, and I’m constantly thinking about whether or not it's right, it’s a sign that it is not right for me. This is what is involved in taking fashion risks, and are integral to developing your sense of style. 

4.    Be Your Own Stylist


Creatively styling outfits may not come natural if you’re not used to doing it. But with practice, you should be able to know what pieces work together, what don’t, and how to add your personal touch. If you've put together an outfit you’re not sure about, and you feel uncomfortable the whole time you’re in it, figure out what's not working, why it isn't working, and what pieces would go better together. If this is difficult to do, go back to tip one and "expose yourself." Whenever I feel like I'm not sure if "this goes with that," I'll look through magazines or fashion sites to get inspo. 

Know the Rules and How to Break Them

It’s important to know traditional rules of styling. What colors typically go with what; what styles are expected to go together, like a flowy bohemian dress with clogs; and what jewelry or make-up is status quo for your outfit such as ethnic chandelier earrings with a bohemian dress and clogs. Once you’ve figure that out, then you can "break rules." For instance, instead of wearing clogs with a bohemian dress, wear a kitten-heeled mule that is both classic and lady like. Or instead of wearing you’re go-to studs with a simple mid-length shift dress, wear really big but lightweight round hoops to give it an edge. One rule of thumb for mixing it up is to do so in a way that adds an unexpected twist but still feels harmonious with the overall look. In other words, make sure every part of the outfit "speaks back" to some part of the other. This is just to ensure that your unexpected twist has context that makes sense.  For instance, if you choose to wear sneakers with a pretty skirt, some other part of the outfit should relate to the sneakers like another sporty item such as a backpack or fanny pack. 

Slight of Hand

As my fashion-conscious friend always says, when it comes to styling it’s all about slight of hand. JCrew was a master at it. Take a classic plaid shirt and make it sexy by tucking it into a pair of high-waisted navy slim silk pants and voila—you have “a look.” It’s still the same classic plaid shirt JCrew has always had but now it has extra interest outside of its preppy element. Think of ways you can add a big impact to clothes you already have with slight changes.

5.    Have Confidence

If you’ve been able to follow through with all the previous points, you should have a certain level of confidence with your look. Confidence is knowing your clothes reflect what you want it to; not worrying about you’re outfit because it feels right to you; and wearing the outfit instead of it wearing you. Some people with even questionable outfits have been able to pull this off simply because they’ve owned it. This has more to do with their individuality and how they carry the clothes than the clothes itself. I’ve always been fascinated by Bridgette Bardot’s effortless style-- the gingham pencil skirt, the ballet-style body suit, the headband, and the messy hair. I was recently intrigued to learn that she never claimed to be stylish. She just had her own ideas and views, and was confident enough to allow her fashion choices to evolve from it. It is this natural evolution of style that captivated our culture so intensely and we still reference her today. What personal ideas and views can you project through your clothing choices?  Remember, fashion is really just a language we use to convey a message to others; and it is in this unique message that are our style takes it's shape.

What do you think about these tips? Are they familiar to you? Are there other tips that have helped you hone your personal style? I’d really like to hear them.