Top Tips for Shopping for Kids’ Clothes in Chicago

If your kid has ever thrown on rain boots with a tutu and a superhero cape to Target, welcome to the club. Styling little ones isn’t always logical, but it is always entertaining.

Shopping for kids' clothes in Chicago comes with a few unique mom‑tested challenges. You know what we mean: the weather shifts faster than your toddler's mood. One day it’s freezing, the next you’re sweating in line at drop‑off, and finding something cute and functional feels like a full‑time mission.

At Lola and the Boys, we believe shopping for your kiddos should be as fun as they are. That’s why we’re sharing our favorite tips to make every shopping trip smoother, sassier, and way more successful. You might be on Michigan Ave, scrolling online in your PJs, or trying to keep up with a kid who only wants unicorns; we’ve got you.

1. Layers Are Life (Especially in Chicago)

When it comes to shopping for kids' clothes in Chicago, layering is essential and makes every outfit more versatile. One outfit has to work for three climates: morning chill, midday sun, and afternoon wind that can actually knock over a kindergartener.

Key layering pieces to keep in mind:

• Soft, breathable tees or tanks
• Cozy hoodies or zip-ups that go on/off easily
• Fun jackets they’ll want to wear (that’s half the battle)

Chicago weather is known for its mood swings. So if the shirt goes under a sweatshirt that fits under a jacket that still lets them buckle into the car seat, you’re winning. Bonus points if it includes sparkles or dinosaurs. Or both.

2. Know What You Have Before You Shop

The drawer full of leggings you thought were all size 7s? Turns out, two of them are now capris. Before heading out for shopping for kids' clothes in Chicago, do a quick closet inventory. It saves time, money, and those “why did I buy another pink hoodie?” moments.

Tips before you shop:

• Pull out what doesn’t fit anymore (and donate the rest)
• Note what’s missing (jeans, tees, layering pieces)
• Make a list, but leave wiggle room for a little sparkle

Being prepared helps avoid buying duplicates or those impulse items that never get worn. It also gives you a better sense of what your child really needs, and what they’ll love.

3. Let Your Kids Help Pick Their Style

Yes, sometimes that means pairing lightning bolt shorts with a dinosaur hoodie and glitter boots. But when kids have a say, they’re more likely to actually wear what you buy.

We’re big believers in giving kids the power to express themselves, within mom-approved limits. Here’s how to keep it fun but manageable:

• Offer 2–3 pre-approved choices (this or that style)
• Ask what colors or characters they’re into right now
• Let them pick one “just because” piece for fun

Building a closet full of pieces they helped choose means fewer style stand-offs at 7:15 a.m. Trust us, the joy in their face when they dress themselves and love the result? Worth it.

4. Comfort Is Queen (Even for Little Kings)

We’re raising tiny humans who run, jump, cartwheel, and somehow manage to get covered in paint, glitter, and pizza sauce, all in the same day. If a piece of clothing can’t keep up, it’s not worth your money.

When shopping for kids' clothes in Chicago, look for:

• Soft, breathable fabrics that won’t itch or pinch
• Stretchy waistbands and flexible fits
• Durable designs that survive more than one wash

At Lola and the Boys, we’ve learned that if it’s not comfy, it’s not happening. So yes, we’re partial to buttery soft joggers, sequins that don’t scratch, and tees that can be tugged, twisted, and tugged again.

5. Dress for the Season, But Always Expect the Unexpected

Chicago moms know: seasonal shopping is less about the calendar and more about what the sky is doing that day. When you're shopping for kids' clothes in Chicago, you're prepping for:

• Sweltering lakefront heat (in May)
• Surprise snowfall (in April)
• October afternoons that feel like July

That means shopping ahead, but stocking smart. Don't overload on one-season items that won’t mix well. Instead:

• Think lightweight layers you can add or peel off
• Pick hoodies and sets that can live through school and snow boots
• Always, always, have a backup outfit in the car

Fashion is fun, but flexibility is a mom’s real superpower in this city.

6. Make Shopping Local (and Kid-Friendly)

When you're shopping for kids' clothes in Chicago, you’re not just buying clothes, you’re choosing who you’re buying them from. And that matters.

Local Chicago shops (like us!) understand the hustle, the weather, and the sass. We design with real kids and real moms in mind. The pieces don’t just look cute, they hold up to recess, pizza Fridays, and spontaneous art class explosions.

Tips for shopping local with ease:

• Call ahead to check inventory or sizing
• Visit on quieter weekdays if you're bringing your mini stylist
• Choose spots with return flexibility (because growth spurts don’t RSVP)

At our Lola and the Boys boutique downtown, your little ones can spin in front of mirrors, test hoodie softness, and point out what they love. It’s shopping, but fun for both of you.

7. Look for Pieces That Pull Double Duty

As moms, we love anything that works harder so we don’t have to. When it comes to shopping for kids' clothes in Chicago, choose items that play multiple roles.

Think about pieces that:

• Work for both school and special outings
• Can be layered or dressed up/down
• Transition between seasons without looking out of place

Clothes that multitask give your budget breathing room and make it easier to pack for playdates, trips, or even weekends at grandma’s.

8. Avoid Pieces That Require Too Much Maintenance

Sure, dry-clean-only looks fancy, but it’s got no place in your laundry pile when your child’s idea of dinner is ketchup with a side of spaghetti.

The best fashion choices for your kid? Pieces that wash and wear like champs. That means:

• Machine washable (every time)
• Stain-friendly colors and patterns
• No zippers that get stuck or buttons that fall off after one spin

Your little one deserves pieces that don’t add extra work to your day. If it can’t go straight from the hamper to the washing machine without a worry, skip it.

9. Growth Spurts Are Real, Shop with a Little Wiggle Room

You blink, and suddenly the pants that fit last week are ankle grazers. Shopping for kids' clothes means shopping for right now and three months from now, because if you don’t plan ahead, your kid will be in P.E. class in pajama pants.

Here's how to shop smart:

• Size up in outerwear, sets, and shoes (room to grow is your friend)
• Stick to true-to-size for jeans, leggings, or anything fitted
• Choose styles with adjustable waistbands or stretchy seams

You don’t need to go full “they’ll grow into it” mode, just a little space to grow is enough. It’s all about balance. You want them to be comfy now, and also not outgrow it before your next coffee run.

10. Bold Patterns Are Mom’s Secret Weapon

There’s nothing wrong with a clean, minimal look, but let’s be honest, bold prints do us moms a major favor. Between stains, spills, and full-body art projects, busy patterns help keep outfits looking fresh longer.

Why bold patterns are genius:

• They distract from life’s little messes
• Kids actually love wearing them (because they’re fun!)
• They make matching pieces easier, hello, capsule closet magic

More fun = fewer fights about getting dressed, and less stress about what they sat in at lunch. Plus, bold prints photograph beautifully. Your family pics just leveled up.

11. Choose Versatile Shoes That Go the Distance

Shoes are the make-or-break for the whole outfit. When shopping for kids' clothes in Chicago, don’t forget that what’s on their feet needs to handle everything from jumping in puddles to running up playground slides (backwards, obviously).

Smart shoe picks:

• Sneakers that match multiple outfits
• Boots that are weather-friendly and easy to clean
• Slip-ons or Velcro for kids still learning to tie

A good pair of shoes means fewer morning meltdowns. And if you’ve ever tried to lace boots at 7:42 a.m. while holding toast in your mouth, you know how valuable that is.

12. Rotate, Reuse, Refresh

You don’t need a brand-new wardrobe every season. What you need is a smart refresh system that helps you:

• Recycle older pieces into new outfits
• Pass down gently used items to siblings or friends
• Bring in 3–5 fresh pieces per season to give new life to the whole closet

This method keeps your budget in check, keeps closets under control, and keeps your kid’s style fresh without overwhelm.

13. Make Shopping a Positive Memory

Shopping for kids' clothes shouldn’t be stressful; it can be fun. It can be a bonding moment. It can be the start of a giggle-filled fashion show in the living room or a surprise dance party in a dressing room mirror.

Try making shopping feel like a treat:

• Plan mini “fashion days” with your child to browse together
• Turn online shopping into a game: “Pick your favorite top and pants!”
• Celebrate when they make choices on their own

It’s more than a shopping trip; it’s a confidence builder, a memory maker, and a chance to teach them how to feel good in their own skin.

Make Life Easier by Shopping for Kids' Clothes in Chicago with Us

From glitter bombers to emoji-covered joggers, Lola and the Boys is the place where comfort meets cool for kids. If you’re shopping for kids' clothes in Chicago, our shop is made for moms who want their kids to shine without sacrificing practicality. Every piece is fun, functional, and designed to survive both playtime and photo ops.

Shop in-store or online at lolaandtheboys.com and find the pieces your child will actually want to wear, again and again.