shopping trip to build a wardrobe

Shopping Trip & Helping My Sister Upgrade Her Mom Style!

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When my sister, Natalie, reached out to see if I could help her with a style re-do I was all in faster than you can say, “There’s a 50% off sale at H&M!” She’s my older sister by one and a half years. She used to never let me forget this. So much so that I would go to bed, chanting in my sleep, “I am the younger sister. I am the younger sister.”

shopping trip to build a wardrobe

I don’t know if you can relate, but growing up, we did NOT get along haha. And I don’t know if it’s just a family story, but apparently, she even hit me over the head with a hammer when I was little. Even if I wanted to remember it I couldn’t, because, you know, brain damage.

But now, she’s so near and dear to my heart and I truly don’t know what I’d do without her!

So this shopping trip was extra fun and it was exciting to see her get excited about fashion and things to wear. Growing up, she was the athletic girl, and 99% of the time, you would find her in a sporty t-shirt and gym shorts. Trading softballs for swaddles and volleyballs for video cameras, she felt ready to redo her look and I’m sure you can relate to something in her story.

Natalie’s fashion story, struggles, & journey

In her later 20’s and two kids later, Natalie was ready to get rid of some clothes that she’s been holding onto since high school. Clothes that didn’t really reflect who she was or who she wanted to be anymore.

Natalie is also a fellow mom and fellow creative. She not only has her own Youtube channel, but she also runs social media for a popular children’s book series. She works from home so clothes need to be comfy, kid-friendly, and stylish enough for filming and zoom meetings.

She also needs a streamlined wardrobe to make the mornings go quicker and smoother. As a busy mom, she doesn’t really have the luxury of taking 25 minutes to stare at her closet to pick out an outfit. I mean, who does? But this doesn’t mean she just wanted to grab a ratty t-shirt and old worn shorts either. She desired to look good too. Is this too much to ask? Nope. This is the exact thing you should aim to have with your wardrobe. And guess what, you can achieve it!

I know some of you have felt a little hopeless in this area but I’m here to say, it’s 100% possible to have a wardrobe that you love and that fits with your lifestyle. Whether you’re a stay-at-home mom, a teacher, a nurse, a creative, a work-at-home mom, or even retired, whatever your stage in life, a streamlined and comfortable wardrobe can be your reality. Whether you have $400 to spend on clothes or $4,000.

Using my eBook as a reference, Natalie handled the style discovering, wardrobe tossing, and color finding part herself. But when it comes to the shopping part, here’s how we made that streamlined wardrobe for Natalie a reality! And though our styles aren’t exactly the same, she leans more towards preppy hipster while I lean more towards Frenchy chic, there’s a lot that is similar and fashionable clothes aren’t limited to just one style.

Our shopping trip

We did the majority of shopping at H&M, Natalie’s favorite store. If you can, shopping in person is extremely helpful so you can see, touch, and try on the clothes! We were looking for clothing items that fit her desired elevated mom style with a hint of preppy hipster in muted, Scandinavian-inspired tones. She had a pretty good idea about what she liked and felt comfortable in, so it was a matter of finding those pieces, plus, I threw in some things that she normally wouldn’t try. 😉

Natalie got the “happy dance” when she tried on comfy yet polished pants. You know the dance, right? The moving and grooving of wow, I look good in this and wow, I feel good too!

Tip: For an elevated casual style, pull-on pants, classy leggings, and tie waist pants will be your best friends! Natalie is just a mere 4 months postpartum, recovering from a C-section. If you find yourself in a similar postpartum stage too, finding high-waisted pants is key. These can hold you all in and make you feel more supported and confident. Personally, I’m a big fan of the Spanx leggings. They’ve got suction!

Natalie shined in v-necks. Growing up sporty, she naturally has well-built shoulders. A v-neck can be very flattering for this body type! Plus, you can see how gorgeous she looks in a shirt dress in that beautiful green autumn color. Personally, I don’t think what “season” you are is the end all be all, but it helps to have a few colors that you look really good in!

lounge shirt | lounge pants

Tip: Flowy dresses with a tie belt are amazing for many reasons. First, the silhouette is freeing and the material is comfortable. The tie belt adds definition to your waist and all in all, it’s a feminine and classy piece. This is the perfect item for someone that finds their weight fluctuates a bit. It can grow or shrink with you and the flowy fabric is very forgiving, concealing any worry spots.

Tip: If you’re looking to elevate your home style, look for matching sets. A matching set instantly looks more put together and intentional. And thankfully, matching lounge sets are all over the place now. Look for more sophisticated styles, such as the blue one my sister is modeling above or anything in a classy material such as cashmere (inspired). Avoid anything too casual, such as waffle knit.

There are several other things that work great for elevated mom style. First, oversized button-downs. These look very classy and when you find one in a relaxed fabric, they’re comfortable too. They look great with leggings, shorts, or pants. Wear it buttons opened or buttons closed. However you wear it, it can make a very chic ensemble!

Secondly, don’t overlook leggings: a mom’s best friend. These days, there are leggings with details that look more elevated than your basic cotton.

On the topic of bottoms, joggers are a great option too. They’re very stylish and typically a tad more comfortable than structured jeans. Joggers pair perfectly with her favorite shoe choice, Birkenstocks.

Tip: Whatever your style, it’s important to make sure everything flows well with each other. For example, my favorite mom shoe choice is a mule slide, and these pair perfectly with all the denim and slip skirts I tend to wear.

Q&A With Natalie

Q: What made you want to rebuild your wardrobe?
Natalie: I was spending too much time (I didn’t have) in the mornings picking out outfits. I had too many and couldn’t find my favorites. I wanted to streamline the process and have fewer pieces.

Q: Did you feel any sort of hesitation?
Natalie: Yes, I didn’t know where to start and it’s hard for me to get rid of my clothes.

Q: What was your favorite part of this process?
Natalie: I loved shopping for clothes. And, I’ve actually started looking forward to getting dressed!

Q: Did anything surprise you when you went shopping?
Natalie: I listened to your advice to try things I wouldn’t normally gravitate to and I liked them!

Q: Any advice you’d give to other women to redo their wardrobe?
Natalie: Just start. Once you get rid of clothes you don’t wear it feels like the weight is lifted out of your closet. Buy clothes you feel comfortable wearing but try to push yourself a little. And don’t be afraid to wear your new clothes!

Q: How did the eBook help you with this process?
Natalie: I loved filling out the color palette and watching my color scheme come together. It was helpful to keep in mind while I was shopping! It helped to limit the millions of options.The “Outfit Ideas” chapter was so helpful since they’re all basic pieces, it’s easy to replicate!

I put together these outfit collages inspired by my sister’s style. If you’re a visual person, this can help you see what pieces you should have in your wardrobe to achieve this style as well as outfit ideas on how you can pair the pieces together.

elevated preppy hipster mom style
elevated mom style preppy hipster
elevated mom style preppy hipster
elevated mom style preppy hipster
elevated mom style preppy hipster

Shop the look:

It was a productive shopping trip but most importantly, Natalie walked away with the mental freedom of getting rid of old clothes and a renewed joy of getting dressed again.

For more adventures of shopping and finding new clothes for my family, check out the post below!

Up Next: Taking My Mom Shopping & Finding Clothes That Flatter


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.