Black FridayDealsBuying guidesBrandsStoresResearchTermsPrivacydeal.ai apps
Black Friday 2026:TVsLaptopsHeadphonesAppleGamingVacuumsKitchenToysSmartwatchesTabletsFurnitureMattresses

© Deal.ai Inc.

AllTravelTechClothesShoesJewelryHomeBeautyOutdoorsToys
This hour's deals
Lennon High Rise Crop Boot in Rosslyn
Lennon High Rise Crop Boot in Rosslyn
−51%
Clothes · ShopSimon

Cropped boots, high rise, ready for anything

Lennon High Rise Crop Boot in Rosslyn

High-rise crop boot jeans in a dark wash — a flattering everyday pair for anyone who likes a cropped ankle.

Deal score 5.7 · Good deal
$77.40$158.00 ShopSimon's regular price

You save $80.60 at ShopSimon

Deal.ai's agents found this deal on November 5. The store may have changed its price since.

Why it's a great deal

  • ShopSimon lists its regular price at $158.00: 51% off by its own figures
  • Rated 4.0 out of 5 by 259 buyers
Visit ShopSimon

Every store we checked

  • ShopSimonNew

    In stock

    $77.40Observed at 11:43 PM
    Visit store
  • Chappy BoutiqueNew

    In stock

    $158.00Observed at 11:43 PM
    Visit store
  • Favorite SisterNew

    Availability unknown

    $158.00Observed at 11:43 PM
    Visit store
Price history and every store's price →

Reading ShopSimon’s product page for the details…

Specs

Size
Size 30
Material
Spandex, Denim
Leg Style
Bootcut
Rise
High Rise
Cropped
Yes
With Pockets
Yes
Closure Type
Button

About the Lennon High Rise Crop Boot in Rosslyn

The Lennon High Rise Crop Boot is a cropped bootcut jean in the Rosslyn wash, cut high at the waist with a button closure and made from a spandex-blend denim for stretch. The cropped boot leg gives it a retro silhouette that works with ankle boots or flats. At $77.40 at ShopSimon as of November 6, 2026, it sits well below its typical full retail, making it a reasonable buy if the size and wash are right.

Best forShoppers who like a high-rise, retro bootcut silhouettePairing with ankle boots, clogs or flatsBuyers wanting stretch denim with a button flyPetite and average-height shoppers after a cropped length
Pros
  • High rise holds the waist and flatters the midsection
  • Cropped bootcut leg reads modern and works with ankle boots
  • Spandex blend adds stretch and comfort
  • Button closure and pockets add a classic denim look
  • Discounted to $77.40 at ShopSimon as of November 6, 2026
Cons

Ask our agent about this deal

It checks today's price at every store, compares the alternatives and answers in about a minute.

Enter to send, Shift+Enter for a new line

  • Cropped length can hit awkwardly on taller shoppers
  • Bootcut leg may run long or flare more than expected
  • Stretch denim can loosen with wear between washes
  • Only 3 stores carry it new, so size availability is limited

    • What reviewers say

    • 4 / 5259 ratings

    Rated 4 out of 5 across 259 ratings, the Lennon crop boot is generally well liked for its flattering high rise and comfortable stretch. Complaints tend to center on length and how the stretch denim holds its shape.

    What people mention
    • FitMixedMany like the high rise and stretch, but some find the cropped length short or the leg roomy.
    • StretchMixedThe spandex blend is comfortable, though some say it loosens after a few wears.
    • SilhouettePraisedOwners like the retro cropped bootcut shape and how it pairs with boots.
    • LengthCriticisedTaller shoppers report the crop hits above the ankle rather than at it.
    • BuildPraisedThe button closure and pockets are called sturdy and well placed.

    Questions and answers

    Is $77.40 a good price for the Lennon High Rise Crop Boot?
    It is a solid discount from full retail and the best of the 3 new prices tracked as of November 6, 2026. If your size is in stock at ShopSimon, it is a good time to buy.
    How does the Lennon crop boot fit compared with a standard bootcut?
    It sits higher at the waist and ends above the ankle, so it reads more cropped than a full-length bootcut. Shoppers between heights may want to size by inseam.
    Does the stretch denim lose its shape?
    Some owners say the spandex blend relaxes after a few wears. Washing and air drying helps it snap back.
    What is the rise and inseam?
    It is a high-rise cut with a cropped inseam; check the size chart for exact measurements, since the crop is the main fit variable.
    What is in the box?
    One pair of Lennon High Rise Crop Boot jeans in Rosslyn. No belt or other accessories are included.
    When is it cheapest?
    Markdowns tend to appear at end of season and around major sale events. The current $77.40 at ShopSimon as of November 6, 2026 is already below typical full price.