How to Hone and Develop Your Personal Style

how to develop personal style

I’ve pored over dozens of style books, many of which outline what they consider to be the fundamental style categories – bombshell, American classic, Bohemian, rock & roll – and suggest essential pieces to procure if you’d like to try these looks out for yourself. Although I often disagree with their requisite item suggestions (Are bright yellow zippered sandals essential to nailing the “mod” look? I think not.), I’m fascinated by how tidily they appear to distill each style into a handful of staples. Making these iconic styles work suddenly seems so simple, laid out there in neatly organized rows of clothing, shoes, and accessories.

But in reality, defining your personal style is no mean feat. You can wear what the monthly magazines tell you to wear, but very little of your true self is likely to shine through all those of-the-moment pieces. You can chose a single, classic style like the ones described in a style guide, but you may feel trapped by the constraints of an aesthetic that is so rigidly defined. You can do what most of us do and wear a hodgepodge of pieces that you’ve accumulated over several years’ shopping time … but, like most of us, you might end up feeling unrefined, undefined, and uncertain.

So what’s a girl to do?

Well, a girl can start with one of the exercises suggested below. These are merely jumping-off points, since personal style refinement is a complex, slow-moving, and deeply personal process. No two women will take the same route to signature-look-creation, and their routes may encompass years of false starts, experiments, and total about-faces. But if you’re drowning in a sea of bland, undefined clothes and accessories, desperate for a lighthouse that will guide you toward a more stylish realm, consider giving one of these babies a whirl:

Identify a celebrity style icon

Celebrities, obviously, are going to err on the side of trendy. But many of them have well-paid stylists whose sole responsibility is to make them look tee-totally gorgeous before they leave the compound for their morning latte. So, you know, celebs generally look pretty damn good and can teach us a thing or two about impeccable style. Are you drawn to Kerry Washington’s classic chic?  Zoe Deschanel’s playful gamine? Rhianna’s arty experimentation? Tear out some magazine images and make an inspiration collage, or create a Pinterest board. Look in your closet and identify pieces you already own that you believe your celebrity soulmate would wear. Examine the pieces that don’t fit in. If your newly elected style icon was FORCED to wear these items, how would she accessorize and style them to make them work? What key items are missing from your wardrobe that will make you more aligned with your celeb of choice?

Identify a non-celebrity style icon

Now be careful with this one, friends, as it must stay firmly in the realm of imitation-as-flattery and never veer off into Single White Female territory. Most of us know at least one woman who looks perfectly put together every day. No matter if she’s running out to buy tampons and ice cream, headed to a business meeting, or jetting off to a posh cocktail party, she always looks chic, natural, and perfectly herself. Never a good idea to become a straight-up mimic, but – as you would with a celeb icon – poke your head into your closet and pick pieces you could imagine this woman wearing.

How would she accessorize and style the items that don’t fit her established look? What about her style would you change to make it your own? If you’re not comfortable emulating a woman in your own social circle, cruise around the wardrobe_remix group on Flickr, Chictopia, or Pinterest. There are tens of thousands of regular people posting full-body outfit photos every day, so you’re bound to find someone in there whose style speaks to you. Once you’ve identified a woman (or man! or anyone, regardless of gender identity!) with style that resonates with you, follow that person and pluck a few key photos to work with. Then follow the closet-refining steps outlined above.

Make a list for today, and one for tomorrow

Not interested in drawing inspiration from anyone other than yourself? Not a problem. Grab a cup of coffee, a notepad, and a pen (or your laptop). Start by listing words that describe your current style. Are you classic, messy, conservative, eclectic, punk, or casual? List the main colors in your closet. Are you all black, white, and gray? Obsessed with autumnal tones like olive, orange, brown, and oatmeal? Does your pastel-packed closet look like a celebration of spring? Describe the cut of your clothes: Boxy, fitted, loose, long, cropped. NOW! Quickly – without thinking too hard – jot down anything about your current style that you find dissatisfying.

Finally, make a list of adjectives and phrases that you WANT to describe your personal style. Do you want to be more colorful, textural, structured, ladylike, edgy, or bold? Do you want to wear skirts all the time, or do more hosiery and jewelry, or be more androgynous? What items do you have now that fit into your ideal style? If you could only buy three new items to help get you moving toward this style, what would they be?

Pick your five faves

Go to your closet and select your five absolute favorite, pedestal-worthy, save-them-from-a-house-fire items. Now, I’m not talking about the pieces that you wear the most often, because those are likely to be basics. I’m talking about the items that called to you – nay, SCREAMED at you – from the shop window, the items that you gratefully paid full price for, the items that draw tons of compliments but only get worn a few times a year. Why do you love them? Take the first item of the five, and build three outfits around it using only clothes and accessories you already own. Do this with numbers two, three, four, and five. Think about the look you’re defining by putting these items at the center of your stylistic universe. How would you describe it? Can you maintain it? Can you style some of your more staid pieces – with accessories, shoes, or embellishments – so that they align with this new direction?

Often, defining your personal style is more about elimination than procurement: You are very likely to require a purge, but less likely to require a shopping trip. Start with what you’ve already got that fits into your desired aesthetic, and work on HOW to wear it. Keep items that show even a glimmer of potential, but jettison items you’re 100% sure won’t work with your chosen stylistic direction. Create a wish list of clothing, shoes, and accessories that will enrich your new look … but try not to shop until you’ve lived inside it for at least a month. You might change your mind, or tweak your ideas. No need to rush the process, as it will become a lifelong one.

I mean it. Since you are not done evolving, your style is not done evolving. There’s no reason to pick a direction today and force yourself to move in that direction ad infinitum. But exploring your personal style is a fantastic way to explore your inner landscape. The choices we make about physical presentation define first impressions, broadcast information about our tastes, and give observers a tiny glimpse into who we really are. Dedicating some time and energy to identifying the boundaries of your look is an investment in self-knowledge and self-confidence that is guaranteed to pay off.

Interested in my own style evolution? Here are some posts that may give you some insight!

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15 Responses to “How to Hone and Develop Your Personal Style”

  1. poodletail

    I’ve nothing to add to this good advice, Sal, except that I surely have enjoyed watching your own personal style develop over the years.

  2. Sewing Faille

    I have a possibly-related question, Sally– what do you do if you’re comfortable with your personal style, but it’s so out-of-whack with the norms of the area you live in that it makes you uncomfortable? I wear a lot of colorful and wacky sundresses, and when I lived in Austin or Los Angeles, this was fine and normal. In Boston, however, it’s…odd. So now I feel as though I can either dress in a way that makes me comfortable in my own skin and stand out in a way I don’t want to, or wear clothes that really don’t feel like me and blend in. Any suggestions?

    • Sally McGraw

      SUCH a great question! Some related ideas are touched on in the body and comments of these two posts:

      But I’ll cook up a separate post as soon as I can.

      Off the top of my head, though, I’d say ponder the individual PIECES that the people around you are wearing that resonate with you. (Blazers, cardigans, heels, button-fronts, etc.) Are there ways you can mix those into the looks that are more “you,” creating a hybrid? Or consider palette: If you favor brights but the Boston palette is neutral-heavy, can you do more bright/neutral mixes? Since it sounds like doing either 100% you or 100% regionally-aligned looks will leave you feeling exposed, finding your way to a hybrid is likely the best solution.

      Does that help? More soon!

    • goreycat

      Thiiiiiiiis. I am very comfortable and happy in my style of dresses and skirts all the time (I own one pair of jeans and one pair of pj pants) but the area I live in? Everyone wears nothing but jeans and yoga pants. At least once a week I hear ‘aren’t you all dressed up’ even I’m wearing a super casual jersey dress and flats. It gets really, really old, and I always feel like I stand out in the crowd – which I don’t really *want* to do all the time!

      • Sewing Faille

        Oh yeah. I heard the exact same thing from one of my friends, originally from the East Coast, who was now living in LA. One of the things I really like about my hometown (Austin, TX) is that you could walk around downtown wearing either a tuxedo or a clown suit and nobody would notice or care.

    • Linda

      Wait, what? I’m in Boston and totally missed the memo about not wearing wacky colorful sundresses. I’m wearing one now! Just wear them, and I will give you the Wacky Sundress Salute when I pass you on the street.

  3. Nebraskim

    This is such great advice. Thanks for distilling into brief piece. The ideas of style icons and also words that describe your still are so useful. If you live, as we do, in a climate with harsh, dominant seasons, you also need to factor that in, I think. I need to think more about my fall/winter dominant seasons far more than my summer season, because it’s shorter and fall/winter is less forgiving in terms of comfort and functionality.

  4. crtfly


    What is Single White Female style? I never saw the movie so I don’t know what type of clothes you are referring to.


    • Birgitte

      Hi! I think the reference is less about the clothes worn by the women, and more about the fact that Jennifer Jason Leigh’s character in the movie utterly crosses the line, and more or less becomes a clone of Bridget Fonda’s character – essentially taking over her life. Imitating someone’s style is ok, stalking them and “becoming” them – not so much. 🙂

      • crtfly

        Thank you for that summary. Now I have a clear idea of what Sally was referring to. I think I will have to track down the movie and watch it. Sounds both intriguing and scary.


  5. Heidi/FranticButFab

    Great ideas, Sally! I’m a big fan of the celebrity icon method myself. I’ve also found that a good approximation of the Fab Five is to look at the things I pull out every time I pack for a vacation. They tend to be the same favorites over and over.