Fun fact: Chic parents dress their children just as cool as they dress themselves. After all, it’s probably not shocking that a tastemaker with a keen eye for fashion would extend that sense of style to their offspring. As the shopping director here at Who What Wear, I probably spend even more time curating outfits for my toddler than I do for myself.
I developed an aesthetic for my daughter early on that appealed to me and I thought fit her vibe at this stage, fully recognizing that she’s a child and will certainly have her own opinions and direction as she gets older (which I’ll fully embrace). But for now, preppy pieces that are comfortable, easy, and look polished have been my jam with her. This includes cute cable-knit sweaters, adorable little leggings and jeans, Mary Janes (paired with ruffle socks), polo dresses, and more. I could go on, but you probably get the picture. There’s more about my specific fashion choices below, but I thought there could be interest in learning more about how other fashion people shop for their children and what’s important to them as they shop for their kids.
Below, you’ll uncover a fall 2025 shopping guide, anchored by wardrobe collections and shopping insights from stylish parents. Keep scrolling for inspiration, along with specific shopping recommendations if you’re looking to add a fresh piece or two to your children’s wardrobe.
Children: 3 (Louie, age 5; Lila, age 2; Lenu, age 8 months)
My Children’s Clothing Aesthetics: “It’s important to consider both comfort and fashion. The priority is their comfort and freedom of movement. We love neutral fabrics, such as cotton, linen, and wool. Next to that, it’s important that the brand fits our identity. I love an oversize fit for Louie. A combination of different materials. Lila usually wears a dress (slightly oversize fit) during winter with tights and ballerinas.”
Shopping Approach: “I look at the quality. It’s important that it’s machine washable. It’s important they feel comfortable in the clothes they wear. Durability is important. I love to shop for new clothes for both Louie and Lila, but I always keep the most beautiful pieces—especially the woolen, cashmere items.”
bobo choses
Compas Wallabee Shoes
ziggy zaza
Kaze Windbreaker
Bonpoint
Justio Gray Striped Set
Child: 1 (age 19 months)
My Child’s Clothing Aesthetic: “Effortlessly timeless with a mix of vintage charm and everyday practicality.”
Shopping Approach: “I try to buy secondhand and vintage pieces whenever I can. Babies grow out of things so quickly that it just makes sense. It’s more sustainable and often far more special.”
Vintage OshKosh B’gosh
Denim Jacket
organic zoo
Shoreline Gingham Lodge Shirt
claude & co.
Blythe Indigo Denim Patch Dungaree
Uniqlo
Newborn Quilted Cardigan
Child: 1 (Adam, age 4)
My Child’s Clothing Aesthetic: “I’d describe my child’s clothing aesthetic as casual-refined—effortless, comfortable, and practical, but always with a stylish, put-together feel.”
Shopping Approach: “When I shop for my son, I love finding durable, versatile pieces that can be mixed and matched, and I tend to gravitate toward natural fabrics and muted tones. I enjoy discovering unique, smaller brands for something different, while also mixing in bigger names like Marni, Margiela, and of course, our favorite Ralph Lauren. It’s very much a mix of high and low, classic and modern.”
“Now that Adam is 4 years and 9 months old, he’s developed his own taste and loves picking out what he feels like wearing. I let him have his own opinion and freedom of choice. I had my time playing with dressing him up when he was a teeny tiny babe, but now I love watching his style personality shine through.”
Children: 2 (son, age 7; daughter, age 4)
My Children’s Clothing Aesthetics: “Comfortable and fun.”
Shopping Approach: “I️ let them pick what they like. I️ believe if you want to raise adults with cool style, you have to let their outfits be ‘ugly’ as kids.”
Bobo Choses
Reversible Padded Jacket
Harry Lambert for Zara X Disney
Sweater
Pigeon Said Please.
Confusion Corner Top
Caroline Maguire, Senior Fashion Director, Shopbop
Children: 2 (Ella, age 12.5; Ryan, age 10.5)
My Children’s Clothing Aesthetics: “Sporty chic. My daughter is very much in her preteen/teen era. All she wants to wear is the coolest hoodies with wide-leg jeans and varsity-inspired T-shirts. My son is the same. He loves bright hoodies and checkered print anything.”
Shopping Approach: “Size up, because they will outgrow this size in one month.”
Lioness
Eivissa Baggy Jeans
Nike
Air Force 1 Sneakers
Polo Ralph Lauren
French Terry Hoodie
Darren Graham, Lifestyle Creator, Stylist, and Writer
Child: 1 (Ducky, age 3)
My Child’s Clothing Aesthetic: “‘Timeless with a twist’ refers to pieces that exude a classic, clean aesthetic yet possess subtle details that elevate their appeal. With Ducky, I always make sure that comfort is at the forefront while still being ready to jump into a random playdate.”
Shopping Approach: “I shop with intention. I want clothes that Ducky can grow into and still look like himself—not just what’s fashionable at the moment.”
Milk Teeth
Retro Rugby Longsleeve
ziggy zaza
Echo Long Sleeve Tee
Tessa O’Connell, Global Public Relations Director at Coach
Children: 2 (Poppy, age 5; Stevie, age 1)
My Children’s Clothing Aesthetic: “Comfy. Cute.”
Shopping Approach: “Anything for my kids has to be comfortable enough to do any activity and durable enough to withstand any meal. I try to stick to patterns that will make them happy, but also easy to throw in the wash. Any mom I know does the same. There’s nothing worse than that extra-special dress you bought only for your child to smear raspberries into.”
Milk Teeth
Polka Dot Pants
Boden
Janie Borg Mix Jacket
(Image credit: The Style Stalker, Stephanie Geddes)
Children: 1 (Madeline, age 22 months)
My Child’s Clothing Aesthetic: My daughter is under two, so I still dress her in clothes I like. Although she’s starting to have more of a say in what she likes. The vibe I lean into is like “cool princess,” with a focus on preppy-meets-pretty staples.
Shopping Approach: I have two separate areas in the closet: one side is for school and the other is for weekends and going out. I look for versatile, durable clothes for school that are always machine washable. When we go out, I dress her in comfortable yet stylish pieces that are sweet and pretty in my eyes.
The Blueberry Hill
Bow Cardigan
Guest In Residence
Louie Sweater
Janie and Jack
Sweater Dress
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