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Picture it, you’re getting ready for work or an evening out. You look in your closet (full of clothes, by the way) and you don’t know what to wear. Too little or too many choices, your indecision and frustration grow as you stand there staring at the clothes waiting for that ideal outfit to jump out at you.

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There are so many components to think about when choosing what to wear. And I’m not just referring to mixing and matching fabrics and pieces, or accessorizing with jewelry. There is also the importance of the activities involved, environment or vibe, and perhaps even the dress code. It’s a lot to process and might seem overwhelming. But I have a trick that I use as my starting point when I’m not sure what to wear and it works every time.

Is it pants, a dress, or a top? It’s not, although they are all important pieces. Are you ready to find out what it is? It might surprise you…

It’s shoes!

No matter what I am doing or where I am going, shoes make a huge difference in my ability to function when I get there and they are my first step to getting dressed.

Exhibit A – The Concert Girls Night Out

Let’s walk through an example. I was helping a client put together some looks for a concert and girls night out. After I asked her a bit about the venue and where she would be going, I needed to know how much walking or standing she would be doing between the train station, dinner, drinks, and the concert itself. I also need to mention it’s winter and snow and ice are on the ground. She wanted to be comfortable, stylish, and feel pulled together without wearing heavy snow boots. After some discussion, we opted for a wedged boot and then backed into the rest of the outfit from there. The wedge would provide the height and look she wanted as well as the necessary tread for the snow and ice. Heels or a heeled boot would have been uncomfortable for her with all of the walking and standing as well as slippery winter conditions.

As soon as we settled on the shoes we could move forward. We absolutely could have chosen a top or other piece first but most people have a few shoes to choose from and I find it easier to start with a smaller category. It also helps narrow down the rest of categories. Not all of the pants fit well with the wedge boot, so we needed to decide which pants would work. Then you can decide on the top based on the pants decision. Once you have it narrowed down to a few options, it is much less overwhelming to decide what to wear than staring at a closet or drawer full of clothing.

Consider your Environment and Activities

Sitting at a desk most of the day or at a dinner the whole evening? Go for it with those heels or shoes that aren’t as friendly on the feet. If you love what you are wearing, you’ll feel more confident. But on the other hand, if you are in pain or feel frumpy because of a shoe choice, your confidence will feel that too. My advice is to think about how much standing or walking you’ll be doing and then match that with your own level of comfort.

One of my mentors in my prior career was always in heels. In fact, she said that flats bothered her feet and she found heels to be much more comfortable. That’s a great example of knowing what makes you feel great and staying true to it! Do what makes you feel most like you!

You can be comfortable and stylish, they are not mutually exclusive contrary to popular belief.

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Are you running to multiple events throughout the day? For example, the office to kids events or date night? You can always bring a change of shoes with you, but you know that you already have your hands full and you’re carrying a million items. Next time, give some thought to your venues and what would make you feel comfortable. Consider if you can make those shoes work for the whole day and then back into an outfit from there.

What do you decide to wear first when getting ready? How do you feel about starting with the shoes?

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