3 Questions to Ask Yourself Every Time You Get Dressed

March 28, 2014

Every time you look in the mirror to get dressed you wonder who the woman is staring back. You shake your head in disbelief. When did you let your wardrobe dwindle to a handful of outfits that are easy and safe—none of which makes you feel fabulous? You sadly acknowledge that you have learned to settle for passable!

Sure, you can get out the door each morning in a jiffy, but it does absolutely nothing to help you feel good about yourself. It can even go so far as to undermine your self-confidence and take up space in your head as you push back the concerns about who might notice that your pants are a tad too short or that you’ve worn the same tired jacket three times this week. You feel aggravated as you tug at the waistband of your pants or keep checking to make sure your bra isn’t peeking out of the neckline. It’s exhausting, but you’ve gotten used to it.

Phew! Take a breath. It does not have to be that way forever and I’m going to show you how to get unstuck.

The truth is that when you feel good about how you look, your self-confidence soars and you waste no energy worrying about what others think. It’s a win-win on so many levels!

The problem is that if your wardrobe has slowly deteriorated and you are at a loss as to how to resuscitate it, the wardrobe gremlins take over and you either spend time convincing yourself that you don’t care or you worry that you do care!

Let me assure you that I am so much less concerned about what others think. As I mentioned, that takes care of itself when you feel good about how you look. So, instead of trying to please everyone else, we can put all our attention to helping you create a look and wardrobe you love. 

I am also not concerned with how much your clothes cost or whether you are dressed to the nines each time you leave the house. Creating a look you love has nothing to do with being fancy or spending a lot of money.

Creating a wardrobe you love has to do with listening to your heart and soul and regularly using a few guidelines to help you dress with intention instead of by default.

Before I share the 3 questions to ask yourself every time you get dressed, let me be perfectly clear. These 3 questions are the first step in creating a look you love. They will not solve every fashion dilemma you’ve ever had. But if you stay true to the heart of these questions you will make progress and every step forward gets you closer to how you want to feel in your clothes.

Start right now.

Take a look at what you are wearing and ask yourself these 3 questions:

1. Do You Love It?

Even if you don’t, on first glance, know why you do or don’t love the garment, it gets the conversation flowing! What do you love about the outfit you are wearing right now? There has to be something or you wouldn’t have put it on. Perhaps it’s simply that it’s comfortable. Great…hold that thought. Maybe it’s that it’s black so you feel like you are getting the best slimming potential from it. Okay…good. It could be that, after really focusing, you realize that you love the neckline because it shows off your neck and shoulders and allows you to wear pretty jewelry. Whatever it is, write it down.

When you practice this question often enough, it will become your fashion mantra.

2. If You Saw It In a Store Today, Would You Buy It Again?

Before you answer, I want to remind you of one thing. The answer has to come from your heart—from the place of, “Yes, I feel fabulous wearing this and I wish I had 3 more.” If it speaks more to that ‘safe’ place of, “well, it’s cozy and I can hide in it,” then that’s not the answer you want. The question is, ‘would you buy it again because you feel amazing wearing it?’

Now, let’s take this to another level. Whether you answer yes or no, make a list of all the reasons why you would or wouldn’t buy it again. This is very valuable information for your next shopping trip! If you wouldn’t buy it again because you feel frumpy in it (even though it is a good color and is comfortable), then that’s good to know. Or, maybe you are somewhere in between. You love the print, but the style makes you feel like you have to hold your stomach in all the time, in which case, note both of these responses.

After a while you will begin to see patterns. Who knew you loved blue so much or that you feel best in a v-neck but that you tend to wear turtlenecks to keep warm. Maybe you love the fabric of the sweater or the ruching on the sides of the dress or the buttons on your favorite jacket. Consider everything. The next step will help you put it all together.

3. What Could You Add/Change To Make This Outfit Feel More Special? 

Let’s go back to the fact that you love blue (or whatever color you discover for yourself) and you prefer v-necks over turtlenecks, but you worry about staying warm. Even if you are dressed head to toe in black or gray, you can add some blue by way of a beautiful scarf. While you might not think the outfit is perfect, you’ve taken a step forward. This is big! You now have the benefit of the beautiful blue color and you can stay warm, too, without resorting to a turtleneck sweater. Here’s a pretty example:

(For help knowing how to tie a scarf check out my scarf-tying video here:https://www.youtube.com/watch?v=tyerfgBfNro)

Another option is that you like the top, but it needs tailoring. Otherwise you will continually fuss with it by trying to keep the sleeves rolled up or folding the hem under so it isn’t too long and that’s just plain annoying. Bring it to the tailor right away. (Even if the top only cost $20 and you have to invest $15, you will have a $35 top that you love and will feel great wearing as opposed to a top that aggravates you every time you wear it.)

Maybe it’s less about adding something and more about combining pieces differently. Maybe the top is great, but it’s long and has some flow to it and instead of wearing it with old, sloppy jeans like you do now, it needs skinny jeans with knee high boots or a pair of wedge sandals.

Or, as we talked about in the first question, if you love the slimming quality of black, perhaps there’s another color that will offer the same advantage. Say, aubergine, merlot or midnight blue. Guess what? This aubergine top from Ann Taylor will be equally as slimming as black:

Chiffon Top Ann Taylor

If you do these three steps regularly you will transform your wardrobe. It has to happen.

When you break the pattern of throwing something on simply because it is safe and easy, you will feel happier when you look in the mirror.

It only takes seconds to stop and ask yourself:

  • Do you love it?
  • Would you buy it again if you saw it in the store?
  • What could you add/change about the outfit to make it feel better?

Start right now and see what happens. What have you got to lose? Nothing. And, each new awareness will bring you closer to feeling fabulous about the way you look, and you deserve to feel fabulous!

Share this post:

Learn how to stop wasting money on things you never wear.
Get Ginger's free e-book and bi-weekly newsletter with fashion secrets: