Here’s a quick look at Windsor's current and upcoming main sales in 2026. Dates and sales may change, so check the official site for the latest updates.
Windsor Sale Calendar 2026
Quick Sales Summary (Text Version)
For quick reference, here is the text version of the calendar below:
January
February
March
April
May
June
July
August
September
October
November
December
Reference Guide
Windsor Store Sales FAQ
When does Windsor have its biggest sales?
The heaviest discounts show up around Black Friday, Cyber Monday, Memorial Day, and the Fourth of July. Windsor also runs a well-known end-of-summer clearance where prices drop sharply on warm-weather styles before fall inventory arrives.
Does Windsor participate in Black Friday and Cyber Monday?
Yes to both. Windsor has a dedicated Black Friday Deals collection on its website, and the discounts extend to physical store locations too. Cyber Monday is online-exclusive and has historically delivered the steepest single-day discounts of the year — past events have advertised major sitewide reductions for that one day only.
What types of items go on sale at Windsor?
Pretty much the full range — dresses, tops, jackets, bottoms, shoes, and accessories all appear in Windsor's sale section. Occasion and formal dresses get heavy markdowns during end-of-season events, while everyday styles like tops and skirts rotate through the sale section year-round.
How deep do Windsor discounts actually go?
During regular sales, markdowns of 20–40% off are common. When clearance kicks in — especially end-of-summer or post-holiday — individual items can drop as low as $9.97 from original prices of $28–$170+. Extra percentage-off clearance events push reductions even further on already-reduced stock.
Is Windsor's online sale different from what's in stores?
Yes — the online Sale and Clearance section on windsorstore.com is a separate offer from in-store pricing. The website's clearance deals are online-only and not valid in stores. That said, Windsor's 350+ physical locations across the US and Canada run their own in-store sale racks.
Does Windsor offer free shipping on sale orders?
Windsor runs free-shipping promotions that activate automatically at checkout — no code needed. The threshold shifts over time, but commonly sits around $40+ or $75+ on qualifying orders. These shipping deals are limited to the 48 contiguous US states and do not apply to international addresses, Hawaii, Alaska, US territories, or PO Boxes.
Does Windsor give any special discounts to military shoppers?
Yes. Windsor offers a 10% military discount for active duty personnel and veterans. This is an in-store only benefit — you'll need to bring valid military ID to a physical Windsor location to redeem it. The discount is not available on windsorstore.com.
Are Windsor sale prices the same quality as full-price items?
Absolutely. Sale items at Windsor are the exact same products as full-price ones — no cheaper materials or cut corners. The lower price reflects past-season styles, overstock, or items being phased out to make room for new arrivals. You're getting the same dress at a fraction of what it cost two months earlier.
Can shoppers outside the US catch Windsor deals?
Windsor ships internationally from windsorstore.com, meaning shoppers outside the US can browse and buy sale items directly. The catch is that free shipping promos are US-only (48 contiguous states), so international orders will incur shipping fees. Windsor also has store locations in Canada, giving Canadian shoppers in-store access to the same sales and clearance events.
Does Windsor have any ways to save that aren't tied to seasonal events?
Yes. Windsor's Sale and Clearance section is live year-round with rotating stock — you don't have to wait for a holiday to find a deal. First-time app users also get 15% off their first purchase on the Windsor app (valid on regular-priced items). The $10 and Under section is another always-on spot that refreshes with discounted tops, skirts, and accessories on a rolling basis.
