Connecticut's tax-free week starts this Sunday.

Public Act No. 26-68 increased the sales tax holiday price threshold from $100 to $300 per item and expanded eligibility to include all backpacks and cleated shoes — the most significant expansion of the holiday in years.

Connecticut's annual sales tax-free week runs August 16 through August 22, 2026 — from the third Sunday in August through the following Saturday.

Six days away. And this year, it's worth planning around more than ever.

A $90 pair of sneakers has always qualified during tax-free week. A $250 pair of boots never did — until now. That change alone makes Connecticut's 2026 holiday meaningfully more valuable for back-to-school shoppers and clothing retailers alike.

What Changed for 2026 — And Why It Matters

Connecticut's tax-free week has been running since 1997 — making 2026 its 27th year. The core structure has stayed consistent: one week every August, clothing and footwear exempt up to a price threshold.

But the threshold hadn't moved with the times. A $100 cap that felt reasonable in the late 1990s covers a narrower range of clothing today as prices have risen. The legislature's decision to raise the cap to $300 is the most significant expansion of the holiday since it began.

Normally, only clothing and footwear priced under $75 per item are exempt from Connecticut sales tax year-round. During tax-free week, the threshold historically rose to $100. For 2026, that threshold jumps to $300 — meaning items that would normally be taxed at the full 6.35% rate can be purchased tax-free during the August 16-22 window.

The practical impact: a wide range of mid-range clothing and footwear that has never qualified before — dress shoes, boots, quality outerwear, athletic gear worn as everyday clothing — now falls within the exemption.

The legislation also adds backpacks and cleated shoes as newly qualifying categories for the first time in 2026.

Cleated shoes are particularly notable — they've historically been excluded as special footwear primarily designed for athletic activity. Their addition signals a broader interpretation of what counts as qualifying footwear during the holiday window.

What's Tax-Free August 16-22

The exemption covers clothing and footwear priced under $300 per item. Here's what qualifies:

Shirts, jeans, dresses, shoes, boots, sleepwear, undergarments, outerwear, hats, gloves, and similar items worn on or about the body — all qualify during tax-free week if individually priced under $300.

Backpacks of any type priced under $300 qualify for the 2026 tax-free week — a new addition under Public Act No. 26-68.

Cleated shoes — soccer cleats, football cleats, baseball cleats — qualify for the first time in 2026.

The $300 threshold applies per item, not per transaction. A shopper buying five $250 pairs of shoes pays no sales tax on any of them — each item individually qualifies.

Connecticut has no local sales tax — the full 6.35% state rate disappears entirely on qualifying items during the holiday. This is different from states like Illinois where local taxes continue to apply during the holiday window.

What's NOT Tax-Free

The expansion is significant — but it doesn't cover everything.

The following items are specifically excluded from Connecticut's tax-free week exemption: special clothing or footwear primarily designed for athletic activity or protective use that is not normally worn except for that activity, and accessories including jewelry, handbags, luggage, umbrellas, wallets, watches, and similar items carried on but not worn on the body in the manner characteristic of clothing.

That means:

• Handbags and purses — taxable during the holiday
• Jewelry and watches — taxable during the holiday
• Luggage — taxable during the holiday
• Protective equipment — helmets, pads, specialty athletic gear — taxable during the holiday
• Items over $300 — fully taxable at 6.35% or 7.75% if classified as luxury
• Electronics — not covered by Connecticut's holiday unlike Massachusetts

The cleated shoe addition creates an interesting edge: cleats are now explicitly qualifying, but other athletic footwear not normally worn except for athletic activity is still excluded. The distinction is footwear that has a plausible everyday use versus footwear that only makes sense on a field or court.

The School Supplies Exemption That Already Kicked In

Before the holiday even starts, Connecticut already made another change businesses need to know about.

Since July 1, 2026, nonelectronic school supplies are permanently exempt from Connecticut sales tax year-round — regardless of whether they're purchased during tax-free week or any other time. Eligible items include backpacks, crayons, lunch boxes, and notebooks.

This is a separate, permanent exemption — not part of the annual holiday. If you sell school supplies in Connecticut and haven't updated your system for the July 1 change yet, that's the first thing to fix before the holiday begins.

The overlap between the two creates a specific compliance question: backpacks are permanently exempt as nonelectronic school supplies since July 1, and they also qualify during tax-free week. For compliance purposes, the permanent exemption applies year-round — during the holiday, both the permanent school supply exemption and the holiday exemption cover backpacks simultaneously. Either way, backpacks are exempt. The practical effect is the same — just make sure your system is treating them as exempt at all times, not just during the August 16-22 window.

How Connecticut's Holiday Compares to Its Neighbors

Connecticut sits in a region where back-to-school tax holidays overlap — and shoppers near state borders often cross to take advantage of the most favorable rules.

Massachusetts held its sales tax holiday August 8-9 — a full week before Connecticut's August 16-22 window — covering most retail items under $2,500 for personal use, including electronics and appliances.

Connecticut's holiday is narrower in category — clothing and footwear only — but now covers a higher per-item threshold than most states and runs seven full days. Massachusetts gave more category breadth. Connecticut gives a longer window.

For families near the Massachusetts-Connecticut border, the strategy this year was clear: electronics and big-ticket appliances during Massachusetts's August 8-9 weekend, clothing and footwear during Connecticut's August 16-22 week.

Connecticut's Sales Tax Structure — Context That Matters

For businesses new to Connecticut sales tax, the holiday doesn't exist in isolation.

Connecticut's standard sales tax rate is 6.35% for most purchases. Luxury items — including clothing and footwear priced above $1,000 — are taxed at 7.75%. B2B SaaS is taxed at a reduced 1% rate. B2C SaaS and digital goods are taxable at the full 6.35%.

Connecticut uniquely requires remote sellers to exceed both $100,000 in gross receipts AND 200 transactions with Connecticut customers to trigger economic nexus — not just one threshold. The "AND" structure means a seller with $500,000 in Connecticut revenue but only 150 transactions hasn't triggered nexus. And a seller with 300 transactions but only $80,000 in revenue hasn't either.

Both thresholds must be crossed for the nexus obligation to apply. For businesses approaching the Connecticut threshold, the distinction matters significantly.

What Retailers Need to Do Before Sunday

The holiday starts in six days. If your systems aren't updated yet, here's what to prioritize in the next 48 hours.

1. Update your price threshold from $100 to $300. This is the most critical change. Your POS and ecommerce tax engine needs to apply the exemption to qualifying clothing and footwear priced up to $299.99 — not just up to $99.99 as in prior years. This single misconfiguration is the most common source of over-collection errors during Connecticut's holiday.

2. Add backpacks and cleated shoes to your qualifying items list. Both categories are new for 2026. If your system had backpacks flagged as non-qualifying because of prior year rules, change that now. If cleated shoes were categorized as non-qualifying athletic footwear, they need to be recategorized.

3. Confirm school supplies are permanently exempt in your system. Nonelectronic school supplies have been exempt since July 1. If you haven't updated this yet, fix it immediately — you may have been over-collecting on school supplies for six weeks.

4. Handle online orders correctly. The sale is considered to have taken place during the tax-free week if the customer pays in full during that window — even if delivery occurs afterward. An order placed at 11:58 p.m. Saturday August 22 qualifies. An order placed at 12:01 a.m. Sunday August 23 does not.

5. Don't split items to qualify. Items normally sold as a unit — like a pair of shoes — cannot be separated and sold as individual items to qualify for the exemption. A pair of shoes priced at $320 is taxable. Splitting them into two $160 charges doesn't make them exempt.

6. Handle "buy one, get one free" correctly. The $300 threshold applies to the item for which there is a charge. A BOGO promotion doesn't allow the retailer to allocate charges to the free item to bring both under the threshold.

7. Confirm Connecticut has no local tax to waive. Unlike Illinois, where local taxes continue during the holiday, Connecticut has no local sales tax. The full 6.35% disappears on qualifying items. Your system should be zeroing out the entire tax — not just a state portion.

The Savings — Under the New $300 Threshold

The expanded threshold changes the math significantly for Connecticut shoppers.

Item	Price	Tax Saved at 6.35%
Sneakers	$180	$11.43
Winter coat	$275	$17.46
Dress shoes	$220	$13.97
Back-to-school outfit	$150	$9.53
Backpack	$85	$5.40
Cleats	$120	$7.62
Full family back-to-school haul	$1,800 across qualifying items	$114.30

A family outfitting multiple kids for school — with clothing, footwear, and backpacks all qualifying under the new $300 threshold — could realistically save $100 or more in a single shopping trip. That's a meaningful incentive, and Connecticut retailers who market the expanded holiday effectively have a real traffic opportunity this week.

For a complete overview of every 2026 state sales tax holiday — including Mississippi's Second Amendment weekend August 28-30, Maryland's tax-free week running through August 22, and Florida's ongoing back-to-school holiday through August 20 — visit our complete 2026 sales tax holiday guide.

Selling clothing, footwear, or school supplies into Connecticut and want to make sure your systems are configured correctly before Sunday? Book a free consultation with our team at sales.tax. We'll make sure your Connecticut compliance is updated before the first transaction of the holiday.