Congrats, you made it through summer! Your kids are (mostly) still acting right, the house is (somewhat) intact, but now you're staring down a back-to-school shopping list that somehow covers different schools, different dress codes, and multiple opinions about what is and isn't cool right now.
Welcome to back-to-school season with more than one kid. It can be a lot, but it doesn't have to be chaotic! Here's how to get through it with your sanity (and your budget) intact.
Start With a List Before You Start With a Cart
This might sound obvious, but most parents skip it and pay for it later in the form of duplicate purchases, missing items, and a second trip they didn't budget for. Before you shop for anything, sit down and build a list for each kid. Include their current sizes, what they actually need versus what they'll ask for, and anything specific to their school & activity schedule.
A few questions worth answering before you go:
Does the school have a dress code that limits certain colors, styles, or graphics? Are there sports, clubs, or activities that require specific gear? What's actually worn out and needs replacing versus what still has life in it? What are the non-negotiables for each kid, the one or two things they’d be devastated not to have?
Getting this set before you walk into our store or open the browser saves you from shopping reactively (and keeps your budget from falling apart).
Shop by Age Group, Not by Kid
Once you have the list, resist the instinct to shop one kid at a time before moving to the next. Instead, group your shopping by category across all of them at once. Set the plan, so you grab all the basics together, then the outerwear, then the shoes, then the extras.
This approach is especially useful at Denny's x Lester's, where you can move across departments for boys, girls, and baby and infant without bouncing between stores. One stop, every age, all covered.
Let the Brands Do the Matching for You
One of the easiest ways to simplify back-to-school dressing is to shop brands with strong, cohesive collections. When everything within a brand already works together, you spend less time mixing and matching styles and more time checking items off the list.
For tween and junior girls who know exactly what they want to wear, Katie J NYC is the place to start. The line was designed specifically for that age group, with fashion-forward tops, sets, dresses, and lounge styles that feel current without trying too hard. Your daughter will reach for these on repeat.

For the baseball kid, Baseball Lifestyle 101 covers graphic tees, hoodies, shorts, and accessories that bring that love of the game into everything they wear, on and off the field. It's gear built for kids who want their wardrobe to reflect who they are.
For the kid who lives in athletic-inspired everything, GOAT USA is the answer. Bold graphics, relaxed fits, hoodies, sweatpants, tees, and accessories that hold up through the school day (and always look good doing it).
Rounding out the lineup: Nike and Adidas for mix-and-match basics across boys and girls, Under Armour for the athlete whose performance gear doubles as everyday wear, and Florence by Mills for junior girls who want soft, easy styles.
Build in a Few Opinions Per Kid
Younger kids can easily get overwhelmed by too many choices. After deciding on the essentials, give your kids a few opportunities to weigh in where it makes the most sense.
For younger kids, parents will likely need to take more control and give them fewer options. Older kids and teens will naturally want more say in what they wear, so involving them in decisions like clothing colors, styles, or sneakers can help them feel confident heading into the new school year while still keeping purchases within the budget and guidelines you've set.
By letting kids have a voice on a few key items, you can keep the shopping trip focused, avoid unnecessary stress, and make sure everyone leaves feeling good about the choices.

Backpacks are a great starting point for this strategy, since kids always have opinions on them and the category is easy to shop quickly.
Don't Forget the Basics
It always happens. You come home with three new outfits per kid…and then realize nobody has socks! Back-to-school basics are the uncool part of the list, but skipping them means another, unscheduled trip.
Before you check out, run through the essentials: socks, undergarments, a layer for the classroom that runs cold, and at least one outfit that can pull double-duty for school pictures. PSD covers the undergarments side with bold prints kids actually like, which makes that particular errand a little more fun than normal.
Use a Stylist and Let Someone Else Do the Thinking
Here's the move most parents don't know about: Denny's x Lester's offers in-store shopping with a stylist who can help you work through the list efficiently, pull items in the right sizes, and keep things moving when the group starts to lose steam. It takes the guesswork out of a trip that can otherwise drag.
Find your closest location at the Denny's x Lester's store locator and plan your visit ahead of the back-to-school rush. With stores in New York, New Jersey, and Florida, chances are there's one closer than you think.
Shop Back to School at Denny's x Lester's
One store, every kid, every age. Shop new arrivals at Denny's x Lester's and get everyone sorted before the first bell.