I don't like the stress of searching through hundreds of deals on Black Friday and Cyber Monday, frantically adding items to my cart to shop in real time. I do like to come prepared for the busiest shopping days of the year with a plan, which is why I've already put the time into deciphering what I'm buying from all of my favorite retailers during the sales.
First on my list is preppy-chic retailer J.Crew. The brand's Cyber Monday Event (insert excited emoji here) involves 500 stylish deals from just $14.50—in fact, if you scroll through its Cyber Monday offerings here, you'll see how many of them are upward of 60% off. Of course, I added a whole host of chic pieces to my cart that are worth buying in preparation for this event. Included in the mix are J.Crew's seriously soft cashmere sweaters, silky lace skirts, and staple black boots. Oh, and I'll be scooping up plenty of holiday gifts too—from handbags to cashmere socks and pretty jewelry.
Keep scrolling for the pieces I'm shopping from J.Crew's Cyber Monday sale and the deals worth snagging immediately.
My Top 5 J.Crew Items Worth Buying During the Cyber Monday Sale
- New Gwyneth Skirt in Chiffon
- Sculptural Orb Earrings
- High-Rise Slim-Wide Jean in 1996 Semi-Stretch
- Cashmere-Blend Trouser Socks
- Isabelle Lady Jacket in Tweed
Perfect to keep you cozy on your morning coffee runs.
Chic and cozy, and ready for the holidays.
Luxe-looking leather gloves you can gift or keep for yourself.
This chic peacoat is everything.
A stunning Lady Jacket for festive occasions.
A chic tennis necklace to style over your sweaters.
This chic puffer is such an elegant length (and more than $200 off).
I'm finally adding this silky slip skirt to my wardrobe—I just need to pick which color. (The black and white are so popular they're on pre-order for January, but honestly, would be worth the wait.)
I always say yes to this perfect basic as a layering piece.
Lean into this season's leopard trend.
I love the vintage look of this.
Elevate your look with these bold everyday earrings (that also come in a gold).
At the top of my J.Crew cart!
The chicest sweatshirt.
A preppy-chic cable-knit cardigan I can't resist.
The dark wash is perfect for dressing up or down.
Style this super-warm sweater with jeans and skirts alike. (Extra 60% off with code CYBER.)
So perfect belted exactly like this.
It's all about sumptuous suede right now. I just have to choose between brown or black—or at 50% off, do I grab both?
Never taking this off.
This will pull together your outfit in an instant.
An elegant turtleneck layer that comes in a slew of colors.
Strappy, sleek, and totally statement making.
Time for some seasonal accessories!
Your new favorite sweatpants.
This trending brushed wool scarf is the perfect gift for anyone on your list—yourself included.
The cozy hat you'll reach for on repeat this winter. (That comes in seven different colors, FYI.)
Classic.
Not a huge surprise that these are best sellers.
Upper East Side vibes.
This luxe sweater is so, so soft.
Essentials in your wardrobe.
The ideal layering top, and another J.Crew best-seller.
I love this fit.
A tailored peacoat you'll love.
This story was published at an earlier date and has since been updated.
-
I'm a FormerReplica Store Buyer, and This Is What I'm Buying From the Incredible Cyber Monday SaleMy expert list.
-
Fashion Insiders Are Carrying Handbags From These Brands In 2026—I Like These 15 Styles Starting At $69The only handbag guide you need for the new year.
-
Every Time Bella Hadid Wears This Sneaker Trend, It Looks So Rich—I Found 13 Pairs Starting At $37Brown sneakers for the win.
-
It’s Almost Ridiculous To Believe These 27 Anthropologie Black Friday 2025 Finds Won’t Sell OutScore 30% off French-girl trench coats, cashmere sweaters, and more.
-
Serious Fashion People Are Overlooking Designer Sneakers for This Rich Pair That's Only $36They're styling them with everything from jeans to wide-leg pants.
-
I'm a Shopping Editor and I'm Live Shopping theReplica Store Black Friday Sale—I Can't Get Over These Fashion and Beauty DealsShop in real time.
-
I Shopped Over 1598 Black Friday Deals—These Are the Best Winter Sweaters Hands Down If You Want to Look Chic and StylishOn-sale, rich-looking winter 2026 sweater trends inside.
-
Wow, the Saks Cyber Week Sale Is Crazy Good—35 Designer Finds You Don't Want to MissCoats, cashmere, handbags, and more.
