As we move into the holiday shopping season, Ashley Stewart’s Cyber Monday event is one many people wait for each year. The sale usually follows right after their Black Friday event wraps up, giving you another chance to save. It’s a short window but often includes some of the biggest markdowns of the season. Based on past years, we have a good idea of when it’ll start, what kind of deals to expect, and which items are usually worth adding to your cart first.

---

Expected Cyber Monday 2025 Sale Dates

Ashley Stewart’s Cyber Monday 2025 sale is expected to begin on Sunday, November 30, 2025, and end on Monday, December 1, 2025. The brand tends to roll right from its Black Friday event into Cyber Monday with almost no gap in between. Unlike Black Friday, which sometimes includes in-store offers, Cyber Monday is typically online only at ashleystewart.com.

Free shipping is also expected to return, with no minimum purchase requirement. That’s been a consistent part of Ashley Stewart’s Cyber Monday offer for several years now, making it easier to grab even smaller items or accessories without extra cost.

Remember, just like most site-wide sales, it won’t apply to gift cards or previous purchases.

---

Expected Discount Levels

Ashley Stewart is known for making its Cyber Monday sale straightforward: 50% off sitewide. That discount usually applies to both full-priced and clearance items. The percentage is taken off the lowest listed price, meaning if an item is already on sale, the extra 50% discount is applied on top of that.

It’s one of the few times of year when almost everything is marked down at once. You can expect most apparel categories to fall under that deal, including dresses, jeans, activewear, coats, and accessories. In addition, free shipping with no minimum will likely remain part of the event, so every order qualifies.

In past years, Ashley Stewart has also layered in smaller category-specific promotions, like an extra 20% off sleepwear. It’s common for them to highlight a few select areas to draw attention to new seasonal collections or clear out stock before the end of the year. We’ll likely see something similar in 2025, possibly tied to cozy or holiday-themed apparel.

If 2024’s event is any guide, discounts on clearance could reach up to 75% off before the additional 50% is applied. That combination can drop some prices to their lowest point of the year. However, those pieces tend to sell out the quickest, especially in popular sizes.

---

Last Year’s Cyber Monday Ad

---

Cyber Monday Ad History

You’ll find some of Ashley Stewart’s older Cyber Monday ads listed below (our archive dates back to 2014!). Then follow the links below to view the last few years of ad history.

• 2024: Page 1, 2 and 3.
• 2023: Page 1.
• 2022: Page 1.
• 2021: Page 1.
• 2020: Page 1.
• 2019: Page 1.
• 2018: Page 1.
• 2017: Page 1.
• 2016: Page 1 and 2.
• 2015: Page 1 and 2.
• 2014: Page 1, 2 and 3.

---

Questions & Comments

What are you planning on getting at Ashley Stewart? Let us know in the comments section located at the bottom of this page.

Known for offering stylish plus-size clothing and accessories, Ashley Stewart typically goes big for Black Friday with steep discounts across their site and stores. Based on what we’ve seen in previous years, here’s everything you can expect: from the sale dates to discount levels, what to shop for, and a few key details to keep in mind.

Black Friday 2025 Sale Start Dates & Duration

Ashley Stewart’s Black Friday event in 2025 is expected to begin on Monday, November 24, 2025, a few days ahead of Thanksgiving. The sale is likely to run all the way through Saturday, November 29, 2025 or while in-stock inventories last.  The sale typically runs bots in-stores and at ashleystewart.com.

Once the Black Friday sale wraps up, Ashley Stewart typically rolls out a separate Cyber Monday event for one day only, falling this year on Monday, December 1, 2025. While the details for Cyber Monday are yet to be confirmed, it’s worth keeping an eye out for this additional opportunity to grab deals.

What Will the Discounts Look Like?

Here’s what you can likely expect in 2025:

1. 50% Off Nearly Everything: If past years are anything to go by, Ashley Stewart is expected to slash prices by 50% across almost their entire store and website. This is a site-wide and store-wide discount, making it a great time to stock up on wardrobe essentials like dresses, tops, pants, outerwear, and accessories.
2. Up to 80% Off Clearance: Beyond the storewide discount, the clearance section is where you can find even deeper savings. Last year, clearance items were marked down by as much as 80%, making it a great opportunity to score major deals on styles from previous seasons.
3. Extra 20% Off Sleepwear (Online-Exclusive): If Ashley Stewart follows their 2024 sale structure, you’ll want to head to their website for an extra 20% off sleepwear. This deal was an online exclusive last year, so it’s worth checking the sleepwear section for cozy pajamas and loungewear at an even better price.
4. Free Economy Shipping on Orders $99+: Ashley Stewart is likely to once again offer free economy shipping on all orders of $99 or more during the Black Friday event.

While these are the expected discount levels, it’s important to note that certain exclusions may apply. Historically, Ashley Stewart has excluded specific items or collections from the sale, so be sure to check their official site or ask in-store associates for full terms and conditions once the sale goes live.

What to Buy During Ashley Stewart’s Black Friday Sale

With 50% off nearly everything and steep markdowns on clearance items, Black Friday is the perfect time to shop for wardrobe essentials, seasonal staples, and even some gift-worthy items. Here are a few categories to focus on:

1. Winter Fashion Essentials

By the end of November, winter will be in full swing, so Black Friday is a great opportunity to snag seasonal must-haves at half the price. Look for coats, sweaters, and outerwear that keep you warm without breaking the bank. Ashley Stewart often carries stylish jackets, puffers, and cozy knits that can easily be dressed up or down.

2. Dresses and Occasion Wear

Whether you’re shopping for a holiday party outfit or something chic for New Year’s Eve, Ashley Stewart’s Black Friday sale is an excellent time to pick up statement dresses. Their collection typically includes bodycon styles, maxi dresses, and sequined pieces perfect for festive events. With 50% off, you’ll have plenty of room to find that show-stopping look.

3. Sleepwear and Loungewear

As mentioned earlier, Ashley Stewart has previously offered an extra 20% off sleepwear during their Black Friday event, but only if you shop online. Be sure to check this section on their website for cozy pajamas, robes, and loungewear sets. With winter approaching, these pieces are perfect for staying warm and comfortable at home.

4. Denim and Everyday Staples

If you’ve been holding off on investing in high-quality denim, Black Friday is the time to dive in. Ashley Stewart’s jeans are known for being both stylish and curve-friendly. Look for options like high-rise skinny jeans, distressed styles, and wide-leg fits—all for half the price.

5. Accessories

Don’t overlook the accessories section during Ashley Stewart’s Black Friday sale. You can expect deals on statement jewelry, handbags, and scarves that add the perfect finishing touch to any outfit. These items also make great gifts for friends and family during the holiday season.

Last Year’s Black Friday Ad

---

Ashley Stewart’s Black Friday Ad Archive

Want to compare Ashley Stewart’s Black Friday sale to the one they ran last year? We’ve got the last several years of their Black Friday ad history posted below so be sure to check it out.

• 2024: Page 1 and 2.
• 2023: Page 1.
• 2022: Page 1 and 2.
• 2021: Page 1.
• 2020: Page 1.
• 2019: Page 1 and 2.
• 2018: Page 1, 2 and 3.
• 2017: Page 1.
• 2016: Page 1.
• 2015: Page 1 and 2.
• 2014: Page 1 and 2.

---

Questions & Comments

How are you planning on updating your wardrobe at Ashley Stewart this Thanksgiving weekend? Let us know in the comments below.