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How to Thoughtfully Enhance Your Personal Style

Five steps to help you tap into your style, be more mindful in your closet and feel great when getting dressed every day.

Photo by Meredith Marquardt with L Photographie.
Photo by Meredith Marquardt with L Photographie.

It’s never too early to start “spring cleaning” in your closet. I’m a strong proponent for regularly culling racks. I understand that’s not how everyone operates, however, incremental audits can go a long way. As you’re setting intentions for the new year, this is a great time to take small, actionable steps that will yield immediate and long term results in the manner of getting dressed each day, which will positively impact other areas of your life. 

Fostering a purposeful wardrobe that authentically reflects your personality and endorses your lifestyle can build your confidence and domino into many other areas of your life. As a personal stylist, I help women reshape how they approach their wardrobe, styling, care condition, and shopping habits. My philosophy is rooted in introducing slight behavioral nudges to help clients understand the implications of getting dressed and how it impacts mood, motivations, performance, engagement, and relationships. 

Clothing is an extension of who you are, which means that your wardrobe should reflect what you like, fits you properly, and is conducive to your day-to-day. It doesn’t mean you have to own a power suit or a killer pair of pumps – while this works for some, it’s not the answer for many. Everyone’s personal style is different and unique. It’s time we embrace individual dynamism entirely.

The following five steps will help you discover more about your personal style and reduce your morning stress (and time crunch) around selecting and outfit. At the same time, you’ll elevate and address your wardrobe with assurance while wearing pieces you love that best suit you individually.

1. Be open-minded and embrace self-discovery

Dressing for you, and expressing yourself authentically, is one of the greatest gifts you can give yourself permission to do. When you remove scrutiny, you begin to eliminate self-doubt. Once you do this and practice regularly, you open yourself up to new possibilities, where you can exist in a state of purposeful decision making, including what you put on your body. When I onboard a new client, I require them to complete a questionnaire that asks everything from their shoe size to what they want to achieve in the year ahead – this sets the stage for self-reflection. 

To explore how you want to feel and dress with confidence and ease, begin to ask yourself questions: Why do I own nine pairs of black pants, and do I wear all of them? Though I love the color lavender, I notice it washes me out in photos, should I be wearing this color? What am I saying to myself when I get dressed in the morning? Is my skirt too tight and distracting me from being fully present in my meeting? Why am I holding onto a stained white t-shirt? 

Take stock of what comes to mind and how you answer these questions. Be open and honest, and allow yourself to wander into unfamiliar possibilities while trying on new pieces. Pay attention to what catches your eye and how it makes you feel, particularly when you put it on your body. Record your response at the moment. I take stock frequently and track by sending myself an email or will dictate a voice note on my phone for future reference. Keep in mind, your style is ever-evolving. 

2. Create a new perspective

Embrace slight change to your physical environment, and by that, I mean your closet, drawers, cabinets, shelves, bins. By restoring order and honing physical organization, your brain will register these visual modifications in a new form. Even the simplest act of dusting your shoes or hanging your coats neatly in the same direction will begin to affect spatial processing. 

A simple way to incrementally refresh your wardrobe is by making mini-edits. When you tackle specific categories, in short, separate sessions, you’ll weed out aged and damaged items or pieces that don’t apply to your lifestyle anymore. The clean-out results in you having an updated inventory of what you own. The Home Edit experts endorse this strategy of starting small and removing clutter, “It’s easier for your mental bandwidth.”

The 4-minute sock purge is a manageable place to begin to create a significant impact. It provides immediate (stress-free) gratification while ushering a new perspective when opening this drawer each morning. Plus, it’s easy to tackle compared to more extensive parts of your closet (goodbye overwhelm). It’s cathartic and practical – no more mismatched socks floating around! All you have to do is pull everything out of your sock drawer and place it on the ground. Immediately remove socks that are missing their partners, then sort into categories (dressy, everyday, athletic, novelty, and so on). Remove tattered, stretched, or damaged. Scan the categories and ask yourself if you need eleven pairs of black knee-high’s, or if seven pairs of grippies are overkill.

3. Get dressed with intention

In the two and a half years I’ve worked directly with women on and in their wardrobes, the same question emerges at every single session: How do I maximize the wear of what’s hanging in my closet?

There’s a myriad of statistics and studies resulting in surveyors saying they wear anywhere between 18-50% of what they own. This needs to change. I’m not saying you have to wear every piece at a high frequency, but rather, make yourself aware of how much goes unworn. When you remove the items that no longer serve a purpose, you’re not only clearing out physical real estate; you’re opening up mental real estate, which in turn will pave the way for new styling possibilities. Sometimes this means less works with more. 

You may be drawn to a particular blouse and only know how to wear it with a skirt or skinny jeans, but unsure of what else to do. Knowing what flatters your body and how it works for your lifestyle, beyond what you like, is part of the toolkit to successful styling. Cultivating a wardrobe that supports multidimensional dressing is the answer to optimizing the pieces you own and reframing your buying strategy going forward. When you buy or wear a garment, pause to consider pairing it with something you’ve never styled it with previously. Try it on together and see how it makes you feel – you won’t know unless you give it a go. If the outcome feels different, but you’re not turned off to it, this is a sign you’re experiencing a new sensation of style-exploration. 

The other day I had a planning call with a client about her upcoming schedule of travel and events. We reviewed her dates, the attire, types of experiences and locales with the goal to shop intentionally and plan outfits accordingly – this way when she gets dressed and packs, she knows exactly what to do without uncertainty. Throughout this process, we collectively share shopping links of items she’s tagged and what I’m recommending that will complement what she already owns. One of the links she texted me was of a tropical isle printed mini dress (ablaze with toucans and palms). At first glance, it’s all the things she loves in a dress: colorful, printed, ruffled, and a flattering, fail-safe silhouette that we’ve identified as her winning cut. Sounds like a win, but I asked her to think about the wearability beyond her Carribean vacation – her response, not likely. 

The point is, as much as we see and fall in love with a dress or a pair of shoes, that doesn’t guarantee that it’s a win for you and that you’ll wear it enough to justify the purchase, no matter the price. Becoming clear on what flatters you, how you pull an outfit together, and what you buy needs to be aligned with your actual lifestyle and day-to-day schedule. 

4. Put something on that makes you smile

Studies show that what you wear can influence your behavior. On top of that, we know all too well that smiling is proven to enhance your mood. When you get dressed in an outfit you love or something new that excites you, relish the moment and then capture the look. Take a photo of yourself in an outfit that brings you joy (think KonMari method) and add it to a folder on your phone. It’s a good reminder of a look you love to wear, and it will spark happiness when you reference the image file in the future. 

In a recent closet session with a new client, we were building outfits from existing clothing and accessories. Her goal was to build out new looks and some guidance for wardrobe improvements. As I was becoming acquainted with her collection, she quickly directed me to her belt section, where she pulled out a yellow smiley-face mosaic belt buckle. Immediately, I smiled. She went on to tell me how much she loves this belt, and how it makes her smile looking at it and even more so wearing it. And while a smile-printed belt may not be for everyone, there’s bound to be multiple pieces in your closet that have you grinning instantaneously, feeling confident and comfortable in what you put on your body. 

5. Converse kindly with yourself  

study conducted by Marks & Spencer in the UK found that women, on average, spend 17-minutes contemplating what to wear every morning. Of the women surveyed, 62% shared that they experience wardrobe rage and frustration. Is this how you start your day? There are implications beyond your racks of clothing, that result from beginning your day in a negative headspace. 

The benefits of self-compassion have a tremendous impact on your brain, and gestures of kindness directed to yourself will lead to greater life satisfaction. Dr. Shad Helmstetter is an expert on self-talk who’s research and training emphasizes the rule of neuroplasticity – repetition is the key to affecting change. In moments of self-doubt and negative talk while putting on clothing, pause and ask yourself where this dialogue is coming from, and how can you reframe your words into honest, gentle, constructive, and loving language. What would you say? 

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