“I’ve reached the age when I think I should look more put together” is a meme I’ve seen across some of my favorite mom feeds on Instagram. While I’ve loved the athleisure gear for working from home, as a mom with school-age kids who is also in their final year as a 30-something, I think it’s time to step up my style a bit. I no longer have to worry about baby puke on my shirt or my kids using my hair to wipe their noses. No one is telling me I should look more put together (at least to my face), but now I’m actually motivated to try.
Enter Maddie, our team’s fashion editor who consistently writes and creates top-performing content and looks readers love for The Everygirl and The Everymom. You may remember she styled our cofounder Alaina Kaczmarski out of her new-mom-of-two $7 t-shirt rut.
So when Maddie agreed to help me step out of my comfort zone with a week’s worth of outfits, I was thrilled … and also a little nervous when I saw some of her picks. I can honestly say I would not have grabbed a single one of these items to try on at the store or clicked to buy. So, here goes my 39-year-old-mom-makeover by 24-year-old style guru, Maddie.
The Before:
Pretty standard work-from-home mom uniform: black leggings, T-shirt, fleece zip-up, blue-light glasses, and my favorite $5 slipper socks (they just got a hole in them—Target, please bring these back!)
My second “before” look: denim shorts and a sweatshirt. I often say my style is comfy and cute, but these are mostly just comfy and boring.
A Message from the Stylist, Madeline Galassi
I feel like I need to start this with a disclaimer: I definitely do not consider myself a stylist. I know that putting together outfits for myself and knowing what’s in style for a season is a different beast than actually styling someone, so this is a fun challenge for me.
It’s also worth noting that Kathy and I have two very different lives. She has two kids that she has to worry about every day, and my life consists of living alone with my little, old dog. We also have slightly different body types to account for—but all that aside, I couldn’t have been more excited to choose outfits for Kathy and (hopefully!) introduce her to some new favorite pieces.
Look #1
The Outfit Plan
Kathy’s Initial Thoughts: I would’ve never bought a jumpsuit, but the jeans and sneaks are in my comfort zone. Can’t wait to try this one out.
The Outfit Reality
Maddie: I personally loved this on Kathy. I know that for me, a black jumpsuit and jean jacket qualifies as one of those outfits that can make me feel like a million bucks (especially these days, when I’m used to only wearing sweats) with little to no effort. I actually really liked it with Kathy’s lighter-wash denim jacket too—overall, I’d give this a B+/ A-.
Kathy: I LOVED this outfit. It was still my comfy-casual style, just taken to the next level. Because I’m so pear-shaped, I really didn’t think a jumpsuit was something I could wear, but the wide leg of the pants made me feel really comfortable. In seeing these pics, I realize I could also invest in a darker wash jean jacket and maybe another pair of white sneakers (mine have ice cream stains and quite dirty soles from two years of wear).
Look #2
The Outfit Plan
Kathy’s Initial Thoughts: I’ve tried some puff sleeves this season and think they’re a little too girly for me. But I do love the high-waisted Universal Thread shorts I bought from Target this summer, so I’m interested to see if the pants version translates.
The Outfit Reality
Maddie: First off, I love this color on Kathy—with her dark hair, I think it’s so flattering and versatile. I actually love the shirt as a whole on her … I think it’s an upgraded T-shirt situation that could be worn endlessly through basically all seasons.
I do think that these pants are a liiiiiiittle big on her, which slightly affects the vibe as a whole. Wide-leg pants are one of those things that do need to fit just right, because sometimes even if they do fit just right, they still look … not right. But in one size down, I think this look would be a winner. For chillier days, the addition of a jacket and pair of booties could make this a fall-appropriate look.
Kathy: This outfit definitely checked the comfy and cute boxes. I’m not sure how flattering the wide-leg pants are on me, they seem slightly too long, but I do love the high-waist. The top was also a fun color and great quality—well done, Target. I could imagine the puff-sleeve top being a very versatile piece in the transition from summer to fall.
Look #3
The Outfit Plan
Kathy’s Initial Thoughts: A striped T-shirt dress tends to be as fancy as I go during the week, but I’d love to see if I could branch out a bit with this more sophisticated option.
The Outfit Reality
Maddie: A flowy, A-line dress like this one is one of the most versatile things you can invest in; you can wear it to the literal grocery store or dress it up for work, and either way it’s flattering and comfortable. I actually have this exact dress and wear it all the time, but know it runs slightly big, but I love the way this fits on Kathy. With the brown croc bag, I think it’s a perfect fall look to wear the hell out of before it gets too cold out.
Kathy: I felt so pretty and comfortable in this dress. The sleeves are flouncy and fun. I feel like it’s still fancy enough for a date-night option, but comfortable enough for everyday wear. I feel like this dress could transition seasons with booties instead of sandals. And the gold hoops are a classic accessory I think I’ll be wearing all the time.
Look #4: Date Night
The Outfit Plan
Kathy’s Initial Thoughts: Too sassy and sexy for me, my husband might love it, but I think silky things are too clingy for the lower half of my frame.
The Outfit Reality
Maddie: I’ll admit that dresses like this are a gamble 100 percent of the time. I was half expecting this to go straight to our fail section, but this came out like a dark horse and is actually my favorite look of them all. It is so flattering on Kathy and isn’t one of those slinky dresses that make any flesh on your body stand out through the fabric. I think the color makes it super versatile and appropriate for basically any season.
Kathy: This dress was not clingy at all. In fact, it also checked the comfy box. The material is lined with a thicker fabric, so you wouldn’t even need Spanx underneath. The top is a little big on me, but I think if I had a bigger chest it would have worked perfectly. The straps are adjustable, so that helped with sizing too. I was completely surprised by this one and am even starting to love the tiny purse, even though it could only hold my phone, keys, and a tiny hand sanitizer; all you need for date night (plus, a babysitter). Again, the gold hoops really pull together the outfit.
Look #5: The Fail
The Outfit Plan
Kathy’s Initial Thoughts: Woah, this is very trendy for me … and the dress looks a bit like an old-timey nightshirt.
The Outfit Reality
Maddie: I actually laughed out loud at this one. This is where online shopping will get you every time—this looked cute on the model online but is truly insane in real life, and I can’t imagine who it would actually look good on. It is so big and bulky that it draws the eye in the most negative of ways, and even a chic, chunky belt couldn’t make it bearable to look at. Kathy’s attempt to salvage it below was as good as it was going to get.
Kathy: This was a hilarious fail. I even forgot to take a picture with the purse or shoes because I was laughing too hard. The sleeves on the dress were so oversized, I felt like I was wearing a costume. Maybe if Maddie had been in person to style me, she could’ve helped me with the belt (which is a great belt) and choose the right shoes from my closet to pair with this, but I just couldn’t do it myself. I even tried to do an ’80s-style preppy look with an oversized sweater (which I bought from our 2020 fall capsule wardrobe) and popped collar, but I couldn’t pull it off.
Ahhh, this feels better. Hello old friend—a comfy sweater and my go-to jeans.
But did you notice the snakeskin mules? Those were a Maddie pick. Thanks for the help, Maddie, I’m feeling a little bit bolder and more put together already!
