Every July, I see parents post about completing their back-to-school shopping in one marathon trip. They buy everything on the supply list, grab new clothes, order the backpack, and call it done. I understand the appeal — checking the whole thing off at once feels efficient.
But efficiency and savings are different things. Back-to-school merchandise follows a predictable pricing curve, and buying everything at once means catching some items at their peak price. The categories hit their lowest prices at different times between mid-July and early September. Following the curve instead of fighting it saves $200-400 for a family with two or three school-age kids.
Here's the week-by-week timeline I follow every year, refined over six back-to-school seasons with three kids.
Late July (Weeks 1-2): Basic School Supplies
This is when the supply price wars begin. Walmart, Target, Staples, and Office Depot drop prices on commodities — notebooks, folders, pencils, pens, crayons, and glue sticks — to loss-leader levels to get parents in the door.
You'll see notebooks for $0.25-0.50, Crayola crayons for $0.50, folders for $0.15, and pencils for $0.50 per dozen. These prices are the lowest they'll be all year and are typically 70-80% below regular prices.
Buy all basic supplies during this window. Check the list, buy exactly what's needed, and resist the urge to wait for "an even better deal" — these are already at rock bottom.
Dollar Tree is also excellent for basic supplies. Their $1.25 composition notebooks, pencil pouches, and erasers are functionally identical to the $3-4 versions at office supply stores.
Early August (Weeks 3-4): Clothing and Shoes
Clothing sales intensify in early August as retailers compete for back-to-school shoppers. Old Navy, Target, and Kohl's run their most aggressive promotions.
Old Navy's "back-to-school" event typically offers 40-50% off kids' clothing. Target's kids' clothing section features Circle offers and clearance on summer items that are appropriate for early-fall wear. Kohl's stacks their percentage-off coupons with Kohl's Cash earnings.
For shoes, this is the window. Kids' sneakers from Nike, Adidas, and New Balance see 20-30% discounts at Famous Footwear, DSW, and Kohl's during early August.
My approach: I take each child on a focused shopping trip with a specific list and a per-child budget ($100-120 for clothes and shoes). We hit one or two stores, stick to the list, and leave.
Mid-August (Week 5): Electronics and Backpacks
Laptop and tablet deals peak in mid-August. Retailers know that tech-savvy parents wait for the best prices, and the competitive window is short.
Best Buy, Amazon, and Walmart offer their strongest laptop deals during this week. Chromebooks for students can be found for $150-200 (versus $250-350 regular price). iPads and tablets see $50-100 discounts.
Backpacks also hit promotional pricing in mid-August. Retailers who over-ordered face the reality that school starts soon and unsold inventory is a loss. JanSport, North Face, and Herschel bags at 25-40% off are common.
Late August (Week 6): Tax-Free Weekends
Many states hold sales tax holidays in late August — typically one weekend where clothing, school supplies, and sometimes electronics are exempt from state sales tax. This represents 4-8% savings depending on your state's tax rate.
Texas, Florida, Ohio, New York, and approximately 15 other states offer these holidays. The dates vary by state and year — check your state's department of revenue website in July for current details.
The tax-free weekend is ideal for any remaining purchases you haven't made. It's also when stores run concurrent promotions, stacking their sales with the tax savings for maximum impact.
Early September (Week 7+): Clearance
After school starts, unsold back-to-school inventory goes on clearance. Supply prices drop to their absolute lowest — but selection is limited and unpredictable. This window works for stocking up on non-specific items (extra notebooks, pens, crayons) but not for completing a specific supply list.
Clothing clearance is also excellent in September. Summer clothing marked down 50-70% can serve as warm-weather school outfits through early fall.
The Category-by-Category Price Map
To summarize the optimal buying timeline:
Basic supplies (notebooks, pencils, crayons, folders): Late July. Loss-leader prices at major retailers.
Clothing: Early August. Back-to-school sales events.
Shoes: Early August. Promotional pricing from athletic and shoe retailers.
Electronics (laptops, tablets): Mid-August. Peak competitive discounts.
Backpacks: Mid-August. Inventory clearance pressure.
Remaining items: Late August during tax-free weekend.
Stock-up items and extras: September clearance.
Real Savings Example
Last year, for three kids (grades 3, 5, and 8):
Supplies bought in late July: $68 (versus estimated $120 at regular prices). Clothing bought during Old Navy event in early August: $245 (versus estimated $380 at regular prices). Shoes bought at Famous Footwear in early August: $115 (versus estimated $175). Backpacks bought mid-August at Target: $52 (versus estimated $80). Remaining supplies during tax-free weekend: $34 (saved approximately $2.50 in tax).
Total spent: $514. Estimated regular-price total: $758. Savings: $244.
For a family with more children or higher-grade students needing electronics, the savings from the timeline approach can exceed $400.
The timeline requires about four shopping trips spread over three weeks instead of one marathon session. Each trip is focused on one category, which makes it faster and less overwhelming. And the cumulative savings fund about two months of our grocery budget — which, for our family, is the best return on a shopping strategy I've ever found.
