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The Everyday Guide: How to Discover (and Support) Your Personal Style

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I’ve muttered to myself on numerous occasions that I possessed absolutely no sense of style. In my role as a consultant, I eventually stumbled upon a satisfactory formula; but my clothing expertise out of work quickly become a long-standing challenge.

Getting dressed (especially for an event) would often feel befuddling. I would be left with a complete mess of cast off clothing as I walked out the door — after trying on literally everything in the recesses of my closet. I did not feel well-heeled and would secretly berate my propensity to gravitate toward the same items.

Nothing seemed to work as it should.

I was purchasing clothing, but still had nothing to wear.

I was certainly on the fast track to style oblivion & knew it.

But lately, I’ve discovered that I had just about everything dead wrong concerning this situation. There was always style gold right in front of me — I simply wasn’t listening.

The truth of the entire style matter is this: the longer we fight our own fashion instincts, the longer we delay the birth of our own signature style.

That needed to change. Why own a wardrobe that didn’t support me and my own identity?

So — here are few things I’ve learned about discovering & supporting that style:

  • Examine your style history. Remember the advice that when college is over, you need to move on. This advice goes wrong on a couple of levels. First, this is a period in our lives when we start to realize what actually works. Secondly, we are motivated and willing to put in the effort to support that style. With the reincarnation of so many trends (think of the slew of available jean options now), it is likely that an outfit you perfected then — could be the solid foundation of your style now. Style Hint: If you have saved much-loved items from that period of time, notice any trends (item, colors, texture.)
  • Feedback (even negative feedback) holds clues. From the time I hit my teenage years, there was constant commentary about my love for shades of brown. (My mother would have preferred to dress me in red pleather — and she tried.) Yet now, I would consider my consistent penchant for earth tones, to be my greatest style strength.
  • Lean into your clothing obsessions, especially if they fuel confidence. At 16, I felt emboldened by my first blazer. Whatever your confidence item or silhouette is — go with it. Take Allison Bornstein’s advice about your signature style: REPEAT what works. Style Hint: Best blazers for the price: H & M’s double breasted classics. At a luxury price point: Veronica Beard’s tailoring is beyond wonderful.
  • Once you find a “Style Blueprint” be persistent. In fact, you might truly have found your style — yet you haven’t found (or cannot find) the right pieces to fulfill that destiny. Style Story: I have always been a huge fan of wide leg paints. However, finding them was a challenge for years. Keep looking. Try vintage & resellers. If you are lucky enough to discover a hard to find piece currently being made, make that purchase before it floats “out of style” (possibly in multiples).
  • Prepare, prepare, prepare. Try on clothing combinations well before you might actually need them. (Donate/swap what doesn’t work, what does not fit or doesn’t help you feel confident.) One sobering style rule: it is nearly impossible to find the right piece of clothing or outfit in the moment of need.

Style isn’t always effortless. However, it is worth the time spent — when the outcome offers more joy with fewer moments of wardrobe panic.

What are the staple items of your personal style and where do you find them? Share your knowledge with other readers.

Live.Work.Think.Play shares observations concerning a wide array of topics from founding a company — to the perfect gift. It is designed to share lessons learned from a variety of perspectives.

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