What the Women of Wear + Where + Well are Wearing

Happy Monday, my friends! I hope you had a great weekend. Today, we are thrilled to introduce a brand new feature : “What the Women of Wear + Where + Well are Wearing.” While the name may be a tongue-twister, the feature is sure to be super fun, practical, and inspiring.

Each month, we will select one versatile piece and show you four ways to style it. The best news? You’ll get to know the Wear + Where + Well team better. I’m honored and grateful to have a wonderfully talented and diverse team of ladies working with me on this website. We are all different ages, from different backgrounds, with different styles and body types, and at different stages of life.

So, no matter what your age, background, style, body type, or whatever, we hope you find inspiration in this new series!

1 White Midi Skirt, 4 Ways

This month, the four of us all agreed this J.Crew white midi skirt is perfect for everyone this summer! Besides looking good, it’s super practical. Elastic waist and pockets! What could be better?

Keep reading to see how each of us styled it, and for all the details of each of our outfits…

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How Carrie Wore It

Founder and Editor Carrie: 

Not surprisingly, I stuck with my usual colorful, bold, feminine style. My idea started with wanting to wear this gingham shirt again. You might remember me wearing it with a gingham dress while in Key West. The shirt is so soft and comfortable, plus it comes in five colors! This time, I styled it by rolling up the sleeves and tying it in the front.

Then, I simply had to add in this super fun pom pom clutch. My friend Amanda spotted this clutch recently, and she knew I needed it! Don’t you just love those enabler friends? Ha. The clutch has every color in the rainbow, so I look forward to wearing it over and over again. Finally, as for footwear, I added one more pop of color. As you can see here, I wore my favorite heels: Aquazzura wild thing sandals. However, as the day continued, I swapped out the heels for these sneakers. The skirt looked just as chic, either way!

A few notes on sizing… For J.Crew items, I’m usually a 2 or 4. I opted for the 4 here, and it was a relaxed, comfortable fit. While I probably could have worn the 2, I’m happy with my choice to go with the 4. And for the record, to give you an idea of the skirt length, I am 5’10”.

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How Ashley Wore It

Graphic Designer and Photographer Ashley:

I’ll be honest: this skirt was outside my comfort zone! With two little ones, I am always worried about keeping white clean. But, I fell in complete love with this skirt!

Having just had my second baby girl five months ago, I was worried this just wouldn’t fit or flatter my new shape. But, the thick waistband and stretch eased those worries immediately. I ordered a 10 to be safe (I just haven’t gone clothes shopping yet), and it fit me comfortably. I know that as I lose more of the baby weight, it will continue to work for me.

As a momma with two girls under 3, I just don’t get dressed these days. I’m in gym clothes and outfits that can be worn to the park or children’s museum most the time. This skirt was a nice change of wardrobe. So, for this look, I kept it within my comfort zone — mom bun and all! I styled it with my favorite neutrals: this olive green cargo jacket and a black tank.

For practical reasons, I wouldn’t necessarily wear this for an all day outfit with my baby girls. This would be a Sunday morning church or going out with girl friends kind of outfit for me. I look forward to adding this skirt to my capsule wardrobe. It will be on heavy rotation this summer!

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How Hannah Wore It

College Intern Hannah:

I absolutely adored this skirt – the flow, the detail, the color… You can never go wrong with white, especially in the summer!

Being 5’3″ tall, I was worried it would be too long and I’d have to add it to my never-ending “needs alterations” list. Surprisingly, though, the length was ideal and it didn’t need hemming. Hooray! I fluctuate between sizes 0-4 in all articles of clothing and for this skirt I ordered a size 2 and it fit perfectly.

As a college student, I am constantly running from classes to sorority meetings to drink dates with friends. Pulling together a comfortable, versatile, and chic outfit while being sleep deprived from an all-nighter of studying can be difficult! I try to resist the urge to just throw on an extra large t-shirt and Nike gym shorts. Instead, I try to wear outfits that exhibit my style: urban and simple with pops of color. And this outfit fits all those criteria!

For this look, I paired my favorite items of the season: a graphic tee, sneakers, cat-eye sunglasses, diamond studs, and a choker. This outfit will definitely be a go-to look for my busy days. It is classy enough for meetings and hip enough to wear to the bar! My tips: keep it classy, keep it comfy, keep it simple.

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How Maritere Wore It

Lead Photographer Maritere: 

A white skirt is a must in anyone’s closet, and this beauty by J.Crew was an instant winner! I loved the textured fabric, romantic length, and above all loved the elasticized waist which adds comfort without taking away from the stylish and modern look.

I am a mother of four and a busy photographer, but that does not mean I don’t like to dress up, especially if I am going out on a date night with my husband or a coffee or meal with friends. So I am always on the lookout for pieces that I can dress up or down and mix and match for my daily routine and then quickly change an item to dress up for going out.

I almost also always incorporate color into my wardrobe as it is representative of who I am as a person and as a photographer. I am definitely a color lover! So that’s exactly how I styled this outfit taking as a base the lovely white skirt! For my look I went for a graphic Yumi Kim v-neck silk blouse, a colorful pair of Franco Sarto stacked heel gladiator sandals, a fringed black and white Sam Edelman handbag, neutral gold and white statement earrings by Kendra Scott, and a colorful Isabel Marant bracelet. I know I will be wearing this outfit, and all these pieces over and over again!

On a side note, these sandals have a very comfortable heel which allow me to wear them all day long. On this particular day I wore them from 7 am until 9:30 pm while shooting and running around town. And as far as skirt, you might be able to go down a size from your regular size, depending on your waist size and how ample you like your skirt to be. As we mentioned, it does have an elastic waistband, plus the skirt style is ample on hips.

Did you enjoy this new feature? We would absolutely love to hear your thoughts!

Also, since it’s Monday, be sure to check out the latest “Carrie Curates” on the home page for my top picks of the week. Also, check out the continually updated Wear + Where + Well Boutique for all my favorite finds.

Thanks for being part of the community here. Have a great week!

Photos by Maritere Rice and Ashley Cardoza

Read more about the Wear + Where + Well team here

Shop the Story

Worn by all : J.Crew Bradbury cotton skirt – under $100! (similar option here)

Carrie’s look : J.Crew gingham crinkled cotton-blend poplin shirt (also here) – under $100! | Santi pom pom clutch | Aquazzura wild thing sandals (also here) | Fendi retro octagon sunglasses (on sale!) | Nars heat wave lipstick | OPI gelato on my mind nail polish

Ashley’s look : Madewell cargo jacket (similar here and here) | ribbed knit cotton tank | Veronique quarter strap sandals

Hannah’s look : Zara fruit t-shirt (similar graphic tees here, here, and here) | Nike Air Force 1 flyknit sneakers – on sale, under $100! (similar options here and here) | gold diamond earrings (similar inexpensive option here) | Zara sunglasses (similar here and here) | Aldo ‘Athlonea’ Choker (similar here) | Chris Chang for Mac lipstick | Chris Chang for Mac cream color base

Maritere’s look : Yumi Kim blouse – on sale, less than $50! (similar here) | Sam Edelman fringed purse | Franco Sarto red heels | Kendra Scott earrings (similar here) | Isabel Marant bracelet (similar here)


  1. Bryn Bradsher says:

    So I am obsessed with this shoot! Those BALLOONS!!

    Also, this is such a great series. It’s great to see one item on different body types and with a different sense of style. You all look amazing!!

    Love this!

    xo Bryn

    1. Carrie says:

      Ah, thanks, Bryn! I have a longstanding obsession with balloons. Haha.

      Thanks for saying that! I think it’ll be a really fun series…

  2. Jenn Lake says:

    Such a great post – I love everyone’s spin on such a classic piece! What a fun team of ladies!

    1. Carrie says:

      Thanks so much, Jenn! I appreciate your words of encouragement.

  3. Bella B says:

    This is such great post!!! I love all the different ways you can rock that skirt!! what a gorgeous post carrie

    1. Carrie says:

      Thanks a ton, Bella! So glad you liked it.

  4. Sheri says:

    Hi Carrie,
    This was one of my favourite posts yet that you have done. Loved seeing your team (cool that you have an intern) and the different shapes/sizes and how flattering the skirt can be.

    Please do more of these features.


    1. Carrie says:

      Sheri – that feedback is much appreciated! I’m so glad you enjoyed the feature. We sure are a diverse group of ladies, each with a unique style.

  5. Sydney says:

    You ladies are killing it!! I think I need that skirt now!!! I can’t wait to see what item you do next!! Have a wonderful day!


    1. Carrie says:

      Definitely, Sydney! It’s a great summer staple.

  6. Merritt Beck says:

    Love this post! I am definitely going to be looking forward to these posts every month! I love the idea of showing versatile pieces by using your whole team! So fun!
    xx, Merritt
    The Style Scribe

    1. Carrie says:

      Thanks a bunch, Merritt! I appreciate the feedback.

      I hope you are having a wonderful trip! Xo –

  7. Rena says:

    Love all the looks and each of you looks fabulous. I run a similar feature on my blog that I call Up Down All-Around except it’s just me styling the same item for work, play, and fun. A white midi skirt was my featured item two weeks ago.


    1. Carrie says:

      Thanks, Rena! I’ll have to check out your feature.

  8. Jennifer says:

    What a fun and inspiring post! Love how you all styled the adorable midi — and need that pom pom clutch in my life!

    xo, Jennifer

    1. Carrie says:

      Thanks so much, Jennifer! Isn’t that clutch amazing? 🙂

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