- All Products
- Fashion
- ShopSimon
- Shoes
- Ankle Boots
-
Heeled Ankle Boots
ShopSimon (formerly Shop Premium Outlets) Heeled Ankle Boots
ShopSimon (formerly Shop Premium Outlets) Heeled Ankle Boots
ShopSimon (formerly Shop Premium Outlets) Heeled Ankle Boots
-47%
Bearpaw
Womens Shorty Ankle Boot In Hickory Brown
$40.00
$75.00
ShopSimon
-11%
Vince Camuto
Kortimy Boots Womens Brown Suede Block Heel Ankle Bootie ZAP2198
$40.00
$45.00
ShopSimon
-31%
Corkys Footwear
Womens Goodness Gracious Heeled Boot In Camel Brown
$50.00
$72.00
ShopSimon
-68%
NYDJ
Womens NYDJ Tonesu Boots US 8.5 Saddle Suede Block Heel Ankle Bootie ZPO3475 Brown
$67.93
$210.00
ShopSimon
-35%
Jones New York
Womens Durvin Block Heel Dress Bootie In Brown
$49.00
$75.00
ShopSimon
-20%
Style & Co.
Style & Co Zaharaa Boots Womens Cognac Block Heel Ankle Bootie LION188 Brown
$67.58
$85.00
ShopSimon
-57%
Myraswim
Womens Katherine Genuine Leather Boot In Brown
$65.00
$150.00
ShopSimon
-22%
Style & Co.
Style & Co Saraa Slouch Boot Women Brown Block Heel Mid-Calf Booties LION212
$50.99
$65.00
ShopSimon
-37%
Xti
Womens Ankle Booties In Camel Brown
$81.00
$128.00
ShopSimon
-66%
FAIRFAX & FAVOR
Womens Oakham Heeled Ankle Boot In Elderberry
$159.00
$465.00
ShopSimon
-40%
Lemon Jelly
Womens Comfy Glossy Ankle Boots In Puce Brown
$59.00
$98.00
ShopSimon
-57%
Salvia
Womens Nico Ankle Boot In Cuoio Brown
$64.00
$150.00
ShopSimon
-71%
Ziera
Womens Corban Ankle Boots In Cocoa Brown
$67.00
$232.00
ShopSimon
-52%
La Canadienne
Womens Julieta Stacked Block Heel Boots In Toffee Suede
$269.00
$559.00
ShopSimon
-21%
Style & Co.
Boots Womens Brown Faux Suede Block Heel Ankle Bootie LION388
$47.31
$60.00
ShopSimon
-24%
Rocket Dog
Womens Rocket Dog Mila Bootie Brown Leather Round Toe Ankle Boot JOBB1512
$75.95
$100.00
ShopSimon
-1%
Xti
Womens Comfort Ankle Suede Booties By XTI Brown
$92.95
$94.00
ShopSimon
-83%
L.k. Bennett
L. K.Bennett Leida Leather Ankle Boot Brown
$79.98
$475.00
ShopSimon
-6%
Minnetonka
Womens Torrey Laceup Booties In Brown Multi
$90.00
$96.00
ShopSimon
-27%
Karen Scott
Womens Karen Scott Carleenn Boots Chocolate Suede Wedge Booties ZPO3812 Brown
$69.50
$95.00
ShopSimon
-34%
VALDINI
Womens Jenny Heeled Boots In Grey Suede
$152.00
$230.00
ShopSimon
-22%
Style & Co.
Style & Co Saraa Boot Womens Brown Block Heel Slouch Mid-Calf Booties LION605
$50.99
$65.00
ShopSimon
-78%
L.k. Bennett
L. K.Bennett Margaux Leather Ankle Boot White
$143.98
$650.00
ShopSimon
-54%
Cordani
Womens Piper Western Ankle Boot In Tortora Suede
$211.00
$455.00
ShopSimon
-43%
Matisse Footwear
Womens Caty Ankle Boot In Ivory Snake White
$117.00
$205.00
ShopSimon
-8%
Pierre Dumas
Womens Western Ankle Bootie In Whiskey Brown
$54.00
$59.00
ShopSimon
-21%
Easy Street
Womens Easy Street Dawnta Boots Brown Matte Block Heel Bootie HAWK810
$54.99
$70.00
ShopSimon
-45%
Matisse Footwear
Womens Winona Boot In Cinnamon Brown
$60.00
$110.00
ShopSimon
-66%
Bueno
Womens Keyah Booties In Brown
$69.00
$200.00
ShopSimon
-41%
Xti
WomenS 144442 Ankle Booties In Camel Brown
$58.00
$98.00
ShopSimon
-25%
Mia
Womens Mia Harlow Boots Beige Faux Suede Block Heel Ankle Bootie ZOGG962
$90.00
$120.00
ShopSimon
-25%
-22%
Naturalizer
Claire Boots Womens Cinnamon Pointed Toe Ankle Bootie LION123 Brown
$101.15
$130.00
ShopSimon
-53%
Cordani
Womens Brennen Suede Block Heel Boots In Brown Suede
$200.00
$428.00
ShopSimon
-75%
Stuart Weitzman
5050 Soho Ankle Boots in Black Nappa Leather
$151.00
$595.00
ShopSimon
-79%
Kaanas
Womens Antares Distressed Ankle Bootie In Toffee Brown
$48.00
$229.00
ShopSimon
Chinese Laundry
Womens Davinna Ankle Boot In Brown
$85.00
ShopSimon
-7%
Xti
Womens Winter Booties By XTI Brown
$79.99
$85.95
ShopSimon
-21%
Sun + Stone
Adelinee Boot Womens Chocolate Double Zip Ankle Bootie LION254 Brown
$59.08
$75.00
ShopSimon
-53%
Kork-ease
Womens Helene Lace Up Heel In Grey Brown
$64.00
$137.00
ShopSimon
-20%
Calvin Klein
Broma Womens Black Leather Square Toe Ankle Bootie LION773
$143.65
$180.00
ShopSimon
-20%
Calvin Klein
Broma Boots Womens Black Leather Block Heel Ankle Bootie LION662
$143.65
$180.00
ShopSimon
-36%
Birkenstock
Womens Ebba Narrow Ankle Boots In Black Suede
$121.00
$190.00
ShopSimon
-20%
Calvin Klein
Broma Boots Womens Black Leather Block Heel Ankle Bootie LION307
$143.65
$180.00
ShopSimon
-44%
Steve Madden
Womens Steve Madden Hint Boots Sand Suede Lace Up Block Heel Ankle JOBB205 Beige
$89.95
$160.00
ShopSimon
-15%
Cole Haan
Womens Cole Haan Holis Boots Black Leather Almond Toe Ankle Bootie ZOGG2169
$170.00
$200.00
ShopSimon
-57%
Diba
Womens Rave Lion Boot In Tan Brown
$76.00
$176.00
ShopSimon
-20%
Calvin Klein
Broma Boots Womens Black Leather Block Heel Ankle Bootie LION135
$143.65
$180.00
ShopSimon
-24%
Xti
Womens Block Heel Booties In Black
$88.00
$116.00
ShopSimon
-34%
Xti
Womens 144670 Round Booties In Black
$93.00
$140.00
ShopSimon
-45%
Vionic
Womens Truckee Heeled Ankle Boot In Black
$105.00
$190.00
ShopSimon
-62%
Jimmy Choo London
Womens Cruz 95 Lace-Up Felt Ankle Boots In Grey Gray
$265.00
$695.00
ShopSimon
-5%
Xti
Womens Wedge Sport Booties By XTI Black
$109.95
$115.99
ShopSimon
-50%
Earth
Womens Collette Callista Boots In Carob Brown
$52.00
$104.00
ShopSimon
-5%
Xti
Womens Booties By XTI A Black
$109.95
$115.99
ShopSimon
-24%
Xti
Womens Cowboy Booties In Black
$89.00
$117.00
ShopSimon
-5%
Xti
Womens Wedge Sport Booties By XTI Black
$109.95
$115.99
ShopSimon
-5%
Xti
Womens Booties By XTI Black
$112.95
$119.00
ShopSimon
-83%
Giuseppe Zanotti
Celeste Ankle Booties in Black Glitter Velvet
$175.00
$1,000.00
ShopSimon
-33%
Xti
Womens 144290 Heeled Booties In Black
$84.00
$126.00
ShopSimon
-5%
Xti
Womens Block Heel Booties By XTI A Black
$122.95
$129.00
ShopSimon
-5%
Xti
Womens Suede Heeled Ankle Booties By XTI Black
$119.95
$126.00
ShopSimon
-39%
Free People
Womens Easy Does It Boot In Black
$90.00
$148.00
ShopSimon
-20%
Xti
Carmela CollectionWomens Leather Booties By XTI Black
$131.95
$165.00
ShopSimon
-5%
Xti
Womens Italian Western Suede Booties Refresh Collection By XTI Black
$121.95
$128.19
ShopSimon
-44%
Free People
Womens Cecille Ankle Boots In Black
$136.00
$242.00
ShopSimon
-4%
Xti
Womens Casual Booties By XTI Black
$123.95
$129.00
ShopSimon
-5%
Xti
Womens Ankle Booties Refresh Collection By XTI Black
$121.95
$128.19
ShopSimon
-40%
Free People
Womens New Frontier Western Boot In Black Suede
$95.00
$158.00
ShopSimon
-46%
Marc Fisher
Women Kiona Ankle Boot In Black
$108.00
$199.00
ShopSimon
-56%
Exé
Womens High Block Heeled Platform Bootie In Beige
$70.00
$160.00
ShopSimon
-74%
Alexander Wang
Kori Cutout Ankle Boots In Black Leather
$202.00
$789.00
ShopSimon
-39%
Schutz
Womens Kaile Mid Glam Booties In Black
$140.00
$228.00
ShopSimon
-15%
FitFlop
FitFlop F-Mode Womens Black Leather Round Toe Platform Ankle Boots RHS8274
$170.00
$200.00
ShopSimon
-26%
Trotters
Womens Trotters Kippy T2060-001 Boots Black Leather Ankle Bootie JOBB216
$139.95
$190.00
ShopSimon
-80%
Nicole Saldanã
BROWN EXCLUSIVE PLAID CHRIS ANKLE BOOTS
$91.00
$455.00
ShopSimon
-3%
Forward
Ankle Boots With Adjustable Coulisse Closure Gray
$399.84
$411.62
ShopSimon
-45%
Pikolinos
Womens Palencia Boot In Black
$138.00
$250.00
ShopSimon
-58%
FLY London
Womens Endo006Fly Boot In Black
$124.00
$295.00
ShopSimon
-16%
FLY London
Fly London Womens Black HELY268 Chelsea Leather Ankle Pull-On Platform Comfort Boots
$201.99
$240.00
ShopSimon
-24%
Vionic
Womens Vionic Truckee J0721L1001 Black Leather Ankle Boots ZOGG1349
$189.99
$250.00
ShopSimon
-31%
Regarde le ciel
Womens Jolene-27 Ankle Boot In Black
$152.00
$219.00
ShopSimon
-78%
L.k. Bennett
L. K.Bennett Chloe Ankle Boot Black
$116.99
$540.00
ShopSimon
-2%
Pikolinos
Pikolinos Womens Black Leather Ankle Bootie Zip Heel Boots - Daroca
$195.99
$200.00
ShopSimon
-17%
Naturalizer
Womens Naturalizer Erica Boots Black Leather Block Heel Ankle Bootie ZAP1671
$190.00
$230.00
ShopSimon
-55%
Chocolat Blu
Womens Lian Boots In Black
$104.00
$229.00
ShopSimon
This season’s trends
- Dolce & Gabbana sandals
- Ecco sandals
- Gray Nike shorts
- Straw hats for men
- Prada sandals for women
- Swim trunks for women
- Moschino sandals
- Gucci shorts for men
- Gucci sandals
- Linen shirts for men
- Dr. Martens sandals
- Nike summer shoes for women
- Skechers summer shoes for women
- Clarks summer shoes for women
- HUGO BOSS sandals
- Cargo shorts for women
- Nike summer shoes for men
- Off-white sandals
- Skechers sandals
- Skechers sandals for women
- Lee shorts for women
- Amiri shorts
- Clarks sandals for women
about products and deals