How to Be Stylish: The Delicate Balance of Openness and Pickiness

After years of working on my own personal style, and seeing many clients of all backgrounds and personalities, I have come to believe that style can be distilled to a single principle:

Great personal style requires being particular about your tastes, while remaining open to surprises.


Every one of my clients falls into one of two camps:

  1. Too picky

  2. Too open

My clients who are too picky remind me of myself! They have formed rules for their closet early in life—and often have a great eye and discerning tastes—but they are unlikely to step outside of the lines. They write off silhouettes, colors, or inspirations because of bad memories that are often based in fear and anxiety. Their strength lies in their self-trust. Their main challenge is to relax some of those rules, without losing sight of their individual tastes. Often times these people miss out on things that make their souls sing, or flatter their figures beautifully, simply because they forget how to imagine and create with the eye of a child.

Precision without reinvention lacks joy and becomes stale

My clients who are too open were an enigma to me at first—I couldn’t understand how someone could love so many things. These clients often have Pinterest boards with thousands of images saved—and usually their inspiration takes many meandering paths, not appearing united or connected. When I worked with a few of these people more closely, their issues and gifts began to make sense: they are incredibly open to feedback and learning but they never formed the habit of discriminating or choosing one thing over another.Their strength lies in their childlike openness and lack of fear. Their main challenge is to come up with rules that are not too oppressive, but still guide their choices in a way that makes building a wardrobe practical and not-overwhelming.

Creativity without constraints devolves into chaos

Unsatisfied with your wardrobe?

When I leave the mall without buying anything it’s because I…

a) Knew exactly what I was looking for (but they didn’t have it!)

b) Saw a lot of things that I liked, but I got sensory overwhelm.

We all have skeletons in our closets. The items I hang onto that I don’t wear are…

A) Disappointing versions of items that I know I would love. I can picture the theoretical better version of them, but I can’t find them.

B) Items that I loved in store, but anytime I go to wear them, something isn’t right.

My body image woes can be summed up as:

A) My body is out of the norm, and I find that most silhouettes don’t flatter me.

B) I can’t tell when something looks good on me.

When someone describes or compliments my style, I feel…

A) Affirmed or excited that people notice my outfits and see what I’m about.

B) Uncomfortable or violated; it feels like none of their business.

When it comes to celebrity style or other people’s fashion, I am…

A) Critical, analytical, and thorough. I break down what works and what doesn’t.

B) Appreciative, impressed, and excited. I’m always discovering combinations I wouldn’t have thought of on my own.

Your responses were:

Mostly A:

You can be too picky! You possess natural gifts of fashionable flair and analytical ability—these are invaluable when it comes to personal style. However, you can be judgmental, stubborn, and critical especially when it comes to your own body and style options. Unfortunately, while your ability to trust your inner voice is an asset, you can become a tyrant to yourself and your choices. Analysis paralysis is real, and your powerful brain can trick you into freezing up and making zero creative choices in your wardrobe. You would benefit from taking a step back and noticing when you are being too judgmental, analytical, or self-limiting.

Mostly B:

You can be too open! You possess natural gifts of wonder, vulnerability, and humility—these make for fertile creative ground. However, you are too susceptible to other people’s voices. You often take in advice from a thousand sources and lose the ability to connect with your innate intuition. You are one of those people who loves to take in information, but you simultaneously are easily overwhelmed. While your openness to inspiration is commendable, you would benefit from setting up boundaries to drown out the noise and focus on what’s most important.

Next Steps

If this advice resonated with you, but you aren’t sure how to proceed, I can help. Book a free consultation with me to get started on solving your wardrobe issues and becoming your best, most fashionable self today!

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