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Back to School Fashion: How to Look Like the Cool Mom

The ads of kids roaming classrooms are everywhere and the evenings are getting a bit cooler…the summer is coming to an end. Another school year is in our near future. Although it is the child going to school, the moms will be just as busy…band practices, PTA meetings and carpools, oh my! But, while it is time to buy the backpacks and pencil sets, moms should remember they, too, need to get themselves ready as well.  But, with all that’s going on, who has the time to make sure they look their best, too? Just throw on the yoga pants and the handiest top in the closet, right? But while your body may be comforted, how is your confidence?

In my work with countless women over the past 27 years, I have seen even the most comfortable outfit result in less comfort for the wearer because it undermined her confidence and inner sense of well-being.

So how do you feel comfortable and confident this fall during those days of running around with the kids?  Here are three commandments that will assure a great start to the school year for you and your student.

Commandment #1: Outer Comfort is Key, But So is Inner Well-being

Throughout my career, I have heard so many women say they don’t feel comfortable getting out of the car when they drive their kids to school because they are embarrassed or feel uncomfortable with what they are wearing…no matter how soft the fabric. They often just throw the easiest thing on to get out the door and not be late. Does this sound familiar? If it is, how confident do you feel (remember, inner comfort as well) when you throw on your yoga pants and a worn t-shirt and then hop in the car?

As a client once said to me after we’d worked together for a bit, “Who knew it would be just as easy to throw on something great as something dreadful. I now have comfy, easy clothes in my closet that I feel wonderful wearing.” This is the key many moms miss. Although the idea here is comfort, the feeling is not just found in the fabric but more and more in how wearing it makes you feel. In fact, not surprisingly, there are many items in your closet that do not exude confidence despite being the most comfortable on your body.

That being said, you want to make sure whatever you wear to catch the first pitch at your child’s game or get them to class on time makes you feel joyfully confident when you hop out of the car; whether you are dropping your child off at school, running into the dentist with her or chatting with other parents at a soccer game.

It is understandable and quite common to realize that if given the option, and if the comfort level were the same, you’d always choose the more flattering look. The reason you’re not is generally one of two things:

  • Either you don’t love the experience of shopping for yourself and always will find a distraction to keep you from doing it or go to the mall on the pretense of buying something for yourself but give up and shop for your kids instead!, or
  • You don’t know how to find things you love so you have (temporarily, at least) given up and resignedly settle for yoga pants and a T-shirt.

If this sounds like you, consider this: Purposefully set aside some shopping time just for you. I understand that if you don’t like to shop this can feel like torture. But, remember, it’s even more tortuous to shop when you’re hurried and frazzled.

When the time comes, you either make your way to the mall or stay home and peruse your favorite website. When you find something that intrigues you, see if you can picture yourself at a school event in it. If, in your mind’s eye, you have your head high and are confident, buy it! If not, while it may look comfortable, you won’t feel fully comfortable once you put it on. Please don’t buy it just to buy something.

Always hold off until you find something you love.

(And, if you don’t know how to find something you love, that’s a different story and there is help available.)

Need some guidance?  Before and after photos of Amanda will illustrate what I’m talking about:


Here’s another idea…I just got a pair of NYDJ jeans that are super skinny.  They feel like leggings, but look like jeans.  Mine are in a ‘natural’ color, but they come in a variety of colors. Or, check out these pull on JAG jeans.  So comfy and no worries about a front tab sticking out through your top:

The idea is to feel pulled together without compromising the comfort factor!

Commandment Two: Be Wary of the Evolving T-Shirt World in Which We Live

The mall is packed with them: “Cute” T-shirts splashed with designs, funny phrases and such or, just as bad, basic, shapeless, oversized T-shirts. As a result of their pervasiveness, it is easy to fall prey to the ease of buying and wearing them. But be careful of this…as I’ve said before, while comfort is key, true comfort comes not only from how something feels physically but also from the self-confidence and delight you feel on an emotional level.

Here are the three things to consider when choosing a top (t-shirt or otherwise):

Color: Make sure the color is flattering.  Don’t always settle for supposed ‘safe’ colors like black, gray or white. They rarely do anything to help you feel joyful and radiant.

Class: Is the wording or design classy? (i.e., per your age bracket as well as what you are trying to portray).  Are you really sure you want to wear the tired t-shirt from the road race you ran 6 years ago or the spaghetti strap top with your bra straps exposed?

Cut:  Does it fit your body well (not baggy or too tight) or does it have interesting design features like ruching, a beautiful print or details like this: (SAMPLE)?

If the answer to any of these questions is no, although comfortable, they will do nothing to make you feel good about how you look. As a result of this, they will not bring the confidence and joy of true comfort. Also, since they don’t have any ruching, prints or design details to add a little ease and camouflage, they can be very unforgiving and will quickly end up in the pile of “What was I thinking?” on the floor of your closet instead of being a new, savored ensemble for the school year.

Commandment Three: Remember, There’s a Reason They Call It ‘Running Around’ – Consider Your Shoes. 

Whether you are chasing a 5-year old at the park, lugging soccer equipment to the field or running to pick up a sick teenager at school, what you wear on your feet is important. Defaulting to clogs, flip-flops and sneakers is the norm, but those are not the only options. Make sure whatever makes it to your feet is both comfortable and good looking (they should make you smile when you walk and when you look down!). You don’t have to be walking a fashion runway to have your shoes add a special spring to your step.

While everyone’s idea of what is comfortable and good looking is different, here’s one idea by Fitzwell:

Or, if you want something more sneaker-like but a little less clunky, try these:

Bottom Line: Confidence Makes the Comfort, not the Cotton

Because of the busyness your children bring to your life (often in addition to a busy work or volunteer life), sometimes you don’t realize until it’s too late and you’ve pulled up to the school that you don’t feel like the “cool/fun/confident mom” you are when you’re wearing comfy top and crocs. While your body may be comfortable, the presentation to others as well as to yourself says something completely different than you want it to and weighs on your psyche. Even if that discomfort is tucked neatly away in the back of your mind—it still nags at you.

Whether the answer is getting a pair of nice stretchy jeans (as I mentioned above) instead of your typical yoga pants or exploring other shoe options to replace your worn clogs, it’s all good as long as it makes you feel good about you. When you take that top or pair of jeans out of the closet and ready it for the drive to school, ask yourself this one question: “Will this make me feel like the amazing woman I am?” Yes, ask yourself this question and listen to the answer.

If not, choose something else or keep a notepad on your dresser and leave a message for yourself to update your ‘back to school’ wardrobe soon so you feel the same sense of confidence you want your child to feel as he or she walks into the classroom on the first day of school.

It is scary how many months, years and even decades can go by while you keep putting off finding a style you love. You don’t want to look back with regrets. Make these changes now and you’ll love getting dressed every morning—even when you’re in a hurry!

(If you’d like a bit more information on how to create your best ‘back to school’ ensemble, contact me for a quick phone consultation. I would be happy to help make this your (as well as your child’s) best back to school experience ever.

Note: All garments pictured here are vegan-friendly (made from fabrics that did not harm any animals).


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Ginger Burr is a fashion stylist and personal shopper serving clients worldwide from metro Boston.