Mistakes Entrepreneurs Make With Their Wardrobe (And How To Fix Them)

August 8, 2020

I was recently interviewed on The Savvy Business  Show Podcast and one of the questions the host and my friend, Hanneke, asked me was “what mistakes do entrepreneurs make with their wardrobes?” This question sparked a really great conversation that I want to continue here with you. Here are the top three ways I see entrepreneurs sabotaging their personal brand by neglecting their personal style. 

You’re Not Planning Your Day-To-Day Wardrobe

I often hear entrepreneurs say “but no one sees me” as an excuse for neglecting their personal style. Here’s how I feel about that: when you run a business how you see yourself will always matter more for your success than how anyone else sees you. How you see yourself determines the energy you show up with in your business. Dressing in a way that makes you feel confident and powerful helps you make confident and empowered decisions.

If this feels overwhelming to you, start by trying to create a uniform (yoga pants don’t count here!) that you wear a few days a week. Play with what you have in your closet and see if you’re just one or two pieces away from having a few outfits you can wear while you’re working that make you feel like a badass entrepreneur. Ask yourself: would you feel confident meeting the client of your dreams if you ran into them on the street? This is a good way to gauge how confident you feel about your outfit choices.

You’re Breaking Trust With Your Audience In Your Branding Photos

I get that photoshoots are nerve wracking. In fact, I’ve seen that people who are usually the MOST prepared person for every area of their life often leave finding outfits for their photoshoot until the day before their shoot because they’re so nervous about it. 

Trying to figure out what types of looks represent your personal “brand” can feel overwhelming. It’s easy to convince yourself that the style that will appeal to our ideal client and the style that feels good to us is different. This can lead to picking outfits that are in the opposite of our authentic personal style. It’s easy to feel like people are expecting up to show up like we’re ready for a fancy, black tie event but here’s the truth: if you’re someone who’s personal style day-to-day is pretty casual, wearing a dress and 4” heels in every one of your branding photos is going to break trust with your audience as soon as they meet you (online or in-person).

It’s absolutely ok to elevate your look for photos but wearing clothes you would never wear in real life is going to evoke an underlying feeling of uneasiness not just when other people get to know you but when you look at the images.  Regardless of how great you are at what you do, a client’s trust can be broken because they’ll feel like they connected with someone who doesn’t actually exist in your marketing.

Picking two to three outfits for your shoot with different levels of formality is a great way to ensure you have images that represent all aspects of your personal style authentically in your marketing.

You See Style As Reward For Your Success… Instead Of An Integral Part Of Success

If I had to pick the number one mistake entrepreneurs make, it’s this one. When you’re running a business there are so many things competing for your time and attention. If you’re someone with a business that’s predominantly virtual, there’s likely long stretches when you don’t see your clients (or anyone related to your business) face-to face. Putting off spending money or time on your wardrobe can seem totally logical. So, you wait until you have a reason to invest and put off having a wardrobe you love until…you feel like you’ve earned it or you’re starting to attract more attention to your business. Or, worse, you have an event to go to.

The most vital aspect of any business is the mindset of the person in charge. Getting familiar with what clothes and outfit combinations make us feel our best before we have to show up to promote our business is a way of giving ourselves the gift of confidence in advance. Trying to figure out your personal style the night before a big event or a photo shoot, while battling the inevitable nervousness that comes with these events makes everything harder than it needs to be. So, here’s a reminder that cultivating your personal style isn’t something you deserve after you achieve some arbitrary goal. Instead, your personal style can be a tool to help you achieve your goals and feel more confident while you’re building your business.

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