Dressing kids can sometimes feel — how shall I put this? — well, impossible. If they’re not growing out of their clothes, they’re picky about colors or styles or sensory stuff (true story: My son had to step into his shirts via the neck for a full year due to a sudden and unexplained fear of putting his head through the hole).
But for Tracy Caliendo, the struggle is even more real. The Manhattan-based mom, social media personality, and hedge fund manager had four children in the span of 13 months between 2017 and 2018, giving birth to daughter Harlow and son Dylan and welcoming twins Piper and Presley via surrogate in between. Add in her teenage son Hunter and that’s a lot of kids for anyone to clothe on a daily basis, much less a fashion-obsessed influencer with a full-time day job.
“We live in the heart of NYC and love to keep up with the upbeat trends and style of the city,” Tracy tells Scary Mommy. “But the clothes still have to be comfortable and good quality for my kids to actually wear them.” And because all parents could use a little style inspo for the warm weather months, we sat down with Tracy to chat about the staple OshKosh outfits that keep her on-the-go brood active and looking cool all summer long.
1. A Transitional Denim And Floral Combo
Tracy’s three daughters — the ‘almost triplets’ that inspired her IG handle — have all inherited their mom’s love of fashion, but 5-year-old Presley takes it to another level. “Presley has a segment called ‘Presley’s Picks’ on our social media,” Tracy shares. “She gives fashion advice and loves to show off her daily look.” This floral dress and denim jacket duo is perfect for those late spring/early summer chilly nights and versatile enough for everything from birthday parties to playground dates.
2. A Matching Set To (Tie) Die For
Even though she herself has a strong fashion sense, Tracy lets her kids dress and style themselves for the most part, both to give them independence and help hectic mornings run more smoothly. “The kids definitely pick out their own clothes, because they love to dress up as much as me.” This adorable dyed-to-match tank top and cartwheel-friendly skort pair perfectly with the eyelet-detailed cap and sneakers for all types of summer fun.
3. A Jumpsuit That Can Be Dressed Up Or Down
When it comes to coordinating looks, Tracy tells Scary Mommy that her crew “loves to dress up and match!” But she also knows that the clothes her kids wear need to be functional as well as fashion-forward. “We’re an active bunch,” she says, “so being able to move around easily is key.” This one-and-done jumpsuit is the perfect mix of dressy and play-friendly. Add gold espadrilles and chic geometric sunglasses for a look that’ll take them from the park, to the library, and even out to special events.
4. Perfect Prints For The Most Fashionable Dude
It’s not just Tracy’s daughters who love to self-style; the boys love a lewk just as much. “They constantly put up social posts of their OOTDs because they are just so excited to share their creativity and a bit of stylish flair,” she tells Scary Mommy. Her littlest guy Dylan loves this slightly retro pairing of a striped henley and palm tree-printed shorts, accessorized with wood shatterproof sunglasses and slip-on sandals.
5. A Look That’s Both Dapper And Durable
As the family’s mini fashion authority, Presley “often helps style her brothers and sisters and is always one to make sure everyone looks their very best,” Tracy shares. This signature Presley pick — a colorful tie-dye jersey tee and pull-on brown shorts with slip-on sneakers — is both adorable and sturdy enough that it’ll hold up no matter what adventures Dylan gets into.