3 Key Questions to Ask Before You Get Dressed

We’ve all done it. Stared into the closet wondering what to wear, with our clothes staring back in an incoherent way. It’s almost like they’re mocking us. But are they?

Of course not. Clothes can’t mock. It’s us. Making mental notes about the weather. About who we might see today. About what won’t itch, cling or squish.

Most of my clients get stuck trying to make sense of what’s in their closets and how to put outfits together fast – even when they love (or like) most of what they have (if they hate what they have we have other work to do).

The best answers to helping you avoid closet consternation lie in asking the right questions.

How do I feel today?


Of course there’s a range of ways you could feel today. Let’s look at a couple of examples I see often.

Excited and motivated to start the day:

Choose your most dynamic piece(s) that will amplify that feeling and energize your creativity!

Facing the day seems daunting (and you feel like you haven’t yet woken up):

Select a “go-to” outfit that requires no brainpower to pull together. Yours could be one piece that you can complete with accessories. For example, you could grab a dress and a great pair of earrings and you have an outfit. Or, choose an outfit people compliment you on (even if you’re not sure why).

Feeling great mentally, but not physically:

Start with a pant or skirt or dress that does not bind around the body. I like shift dresses and clothes that skim but do not cling if I am bloated, tired or like last week, sunburned!

What shoes do I wear?


It’s easy to start from the bottom up. For example, I adjust the height of my heels depending on how much walking I do. On client shopping days, when I am all over the store, I select a low heel.

If I am attending a networking or sales event, but not presenting, I reach for a slightly higher heel for 2 reasons: A higher heel makes me feel more confident, and if there are any men at the meeting, I prefer to stand taller to see eye to eye with them.

Once you have the shoe, think about what skirt pant or dress goes with that shoe. Right there you will eliminate more than a few pieces, and be forced (hopefully in a good way) to choose a top to go with the pants that go with the shoe, and voila – an outfit.

What message do I need to give today?

If you are in the fields of law, business or finance (or giving a presentation to professionals in these fields), consider a suit – matching top and bottom, or at least a jacket with a collar and a lapel. To claim authority, especially as a woman in a man’s field, it’s wise to put yourself on a level playing field dress wise, at least until you can assess the culture and feel of an organization.

To project and maintain approachability and receptivity, go for a less dramatic use of line and shape (unless you are about to become a fashion designer), and wear outfits that represent you at a very deep level. Wearing clothes that unequivocally say “this is me” lets you feel authentic in a way that allows you to be more confident, and gives your listener more reason to hear you.

Practice asking yourself these questions every time you get dressed. And consider that it’s time to start using your wardrobe as a resource that works for you – like you use your house, your car and your money. Using your clothes to change and/or increase your attitude is smart time and money management.

And being conscious of both the outside message of the design elements in your clothing, and how those elements affect you is the secret to a well-loved wardrobe that is effortless to put together.

If that is not the kind of experience you are having with your closet, please feel free to email me with your wardrobe challenge, and let’s get you on your way to getting dressed with ease and joy every day.

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