It’s a season with a long list, but shopping with your children, whether it’s for clothing or school supplies, doesn’t need to be a struggle. These tools will help.

Back-to-school season is here—which means new shoes, clothing, and school supplies. It also means crowded stores, long lines, tired kids, and endless, “Ma, can I have…?”

Shopping with children can sometimes feel like coordinating a small expedition, with different needs, moods, and opinions all competing at once.

Moms—you’ve got this! 

Here are some practical strategies to help make back-to-school shopping a little less stressful—and a lot more enjoyable.

Say “No” Without Feeling Like the Meanest Parent Ever

Do you feel guilty every time you tell your child “no”?

Reality check: “No” isn’t mean. It’s a boundary. And boundaries are an act of love.

Your child isn’t looking for a parent who says yes to everything (even if they think they are). They’re looking for someone who can lovingly guide them and help them make good choices.

One of my favorite parenting tools is to add a “yes” to your “no.”

Instead of simply saying no, acknowledge part of their request first.

“Ma, can I have these shoes?”
“Yes, you can when you’re older and they’re a better fit. This year they’re not the right choice.”

“Can I pleeease get them?”
“I know you really like them. They’re super cute, but they’re just not the right choice today.”

A few more examples:

“Can I have a sleepover?”
“Yes! This week doesn’t work, but let’s plan one for next week.”

“Can I get these 50 glitter pens?”
“Yes! They’d be so much fun for a long Sunday. Today we’re shopping for what your teacher asked for. Let’s remember them for another time.”

“Can I get this skirt? Everyone has it!”
“Let’s try it on and see how it looks. If it works well and it’s something we’re shopping for, we can definitely consider it.”

Starting with a positive response softens the conversation without changing your boundary. It helps your child feel heard, and people—kids included—naturally respond well to positivity.

Set Loving Boundaries

• Be kind, but stick to your plan. If something isn’t in the budget or on the list, it’s okay to say no.
• At the same time, don’t let one outfit become a major battlefield. Choose your battles wisely.
• Remember that every child is different. Some genuinely care much more about clothing than others. Just as we teach our children that fair and equal are not always the same, the same principle applies to parenting. What one child needs may not be what another child needs—and that’s okay.
• Encourage your children to develop their own style. Building a sense of self is an important part of growing up.
• Compliment their taste—even if you’re not buying the item.
• Offer choices whenever possible. If you’re choosing the clothing, let them choose the accessories.
• If trying on clothes is a struggle, create a simple reward system. Every few outfits earns a small privilege or treat.

Stay in the Moment

• Take a deep breath when you start to feel overwhelmed. It will help you respond instead of react.
• Leave younger siblings at home if possible.
• Give older children one-on-one shopping time when you can.
• Ask for help if you need it.
• Keep your budget in mind, but also remember that what looks like a “want” to you may feel very important to your child.

Clothing Shopping: Tips for Survival, Sanity, and Style

Prepare Before You Go

• Check closets before shopping so you know what your children actually need.
• Decide on your shopping goals and budget before leaving the house, and share them with your child.

For example:

“Today we’re shopping for two weekday outfits, one Shabbos outfit, school shoes, and Shabbos shoes. We’re not shopping for boots or sneakers today.”

Knowing the plan ahead of time helps prevent disappointment—and avoids buying a fifth sweatshirt no one really needs.

• Prepare your child for crowded stores and long waits. Bring along something to keep them occupied while they wait.
• If they fall in love with something that’s not on today’s list, snap a picture and save it for a birthday, Chanukah, or a future wish list.

School Supply Shopping: Let’s Make It Fun, Not Homework

School supply shopping doesn’t have to end in tears at Target or wailing in Walmart. With a little preparation, it can actually be enjoyable.

Prepare Together

Sit down with your child and go through the school supply list together.

• Make sure you both understand what’s actually needed.
• Take inventory before buying anything. Check drawers, closets, backpacks, and last year’s supplies.
• Reuse items that are still in good condition.
• If your child needs a dictionary, thesaurus, or Hebrew dictionary that’s only used occasionally, consider borrowing one instead of buying it.

Make It Fun

Let your child choose a color scheme or theme. It’s a simple way to give them ownership while allowing them to express their personality.

As they choose supplies, encourage them to ask:

• Does it match my theme?
• Is it on my school list?
• Will I still love it in a few weeks?

These questions help children make thoughtful decisions while still enjoying the experience.

Remember the Bigger Picture

Practice saying “no” with kindness and confidence. Not every glittery item is a necessity—even if your child insists it is.

At the same time, know your child. Something that seems insignificant to you may feel very important to them because of confidence, friendships, or social concerns.

Set clear boundaries, stay curious, and listen.

Being the parent means balancing firm limits with understanding.

End on a Happy Note

Whenever possible, finish the trip with something enjoyable—a slice of pizza, an ice cream, or another small treat. It doesn’t have to be expensive.

Years from now, your children probably won’t remember which notebook they picked out, but they’ll remember laughing with you, spending time together, and feeling that back-to-school shopping was something you enjoyed as a family.

Back-to-school shopping isn’t just about checking items off a list.

It’s an opportunity to connect with your children, build their confidence, teach thoughtful decision-making, and create positive memories together.

With preparation, loving boundaries, and a little creativity, you’re setting the tone for a confident and successful school year.

You’ve got this, parents. Wishing everyone stress-free shopping and a wonderful year ahead!