Under $500 Finds
Under $500 Finds
Newest First

Saint Laurent Leather Chelsea Boots
Men's Size: 11 | EU 44
62% Off Est. Retail $1,200
- Price: $455.00
15

Bottega Veneta Leather Chelsea Boots
Men's Size: 14 | EU 46
Est. Retail $1,390
- Price was: $285
- Price: $270.75
- Now 5% off is the current price
21

Saint Laurent Leather Chelsea Boots
Men's Size: 8 | EU 41
Est. Retail $1,200
- Price was: $385
- Price: $365.75
- Now 5% off is the current price
33

Saint Laurent Leather Chelsea Boots
Men's Size: 12 | EU 45
Est. Retail $1,200
- Price was: $485
- Price: $388.00
- Now 20% off is the current price
35

Allen Edmonds Leather Chelsea Boots
Men's Size: 8
- Price was: $145
- Price: $130.50
- Now 10% off is the current price
10

Salvatore Ferragamo Leather Chelsea Boots
Men's Size: 10 | US 10
Est. Retail $650
- Price was: $455
- Price: $432.25
- Now 5% off is the current price
9

Santoni Suede Chelsea Boots
Men's Size: 9 | UK 8
- Price was: $115
- Price: $103.50
- Now 10% off is the current price
3

Crockett & Jones Leather Chelsea Boots
Men's Size: 12.5 | UK 11.5
62% Off Est. Retail $585
- Price: $225.00
2

Common Projects Suede Chelsea Boots
Men's Size: 11 | EU 44
Est. Retail $530
- Price was: $345
- Price: $310.50
- Now 10% off is the current price
26

Frye Leather Chelsea Boots
Men's Size: 13 | US 13
Est. Retail $300
- Price was: $95
- Price: $90.25
- Now 5% off is the current price
14

Bottega Veneta Leather Chelsea Boots
Men's Size: 9 | EU 42
Est. Retail $1,390
- Price was: $345
- Price: $310.50
- Now 10% off is the current price
18

Bottega Veneta Leather Chelsea Boots
Men's Size: 9 | EU 42
Est. Retail $1,390
- Price was: $355
- Price: $319.50
- Now 10% off is the current price
18

Saint Laurent Suede Chelsea Boots
Men's Size: 10.5 | EU 43.5
63% Off Est. Retail $1,200
- Price: $445.00
14

Bottega Veneta Leather Chelsea Boots
Men's Size: 8 | EU 41
Est. Retail $1,700
- Price was: $395
- Price: $355.50
- Now 10% off is the current price
12

Bottega Veneta Leather Chelsea Boots
Men's Size: 8 | EU 41
Est. Retail $1,390
- Price was: $395
- Price: $335.75
- Now 15% off is the current price
11

Bottega Veneta Leather Boots
Men's Size: 8 | EU 41
Est. Retail $1,520
- Price was: $445
- Price: $356.00
- Now 20% off is the current price
9

Bottega Veneta Leather Chelsea Boots
Men's Size: 6 | EU 39
Est. Retail $1,390
- Price was: $435
- Price: $369.75
- Now 15% off is the current price
9

Alexander McQueen Leather Chelsea Boots
Men's Size: 10.5 | EU 43.5
- Price was: $395
- Price: $335.75
- Now 15% off is the current price
5

Sandro Leather Chelsea Boots
Men's Size: 11.5
Est. Retail $580
- Price was: $145
- Price: $116.00
- Now 20% off is the current price
5

Ralph Lauren Purple Label Leather Colorblock Pattern Chelsea Boots
Men's Size: 8
- Price was: $395
- Price: $335.75
- Now 15% off is the current price
5

To Boot New York Leather Chelsea Boots
Men's Size: 12
- Price was: $105
- Price: $99.75
- Now 5% off is the current price
2

Burberry Leather Chelsea Boots
Men's Size: 11 | EU 44
- Price was: $285
- Price: $242.25
- Now 15% off is the current price
16

Burberry Leather Chelsea Boots
Men's Size: 9.5 | EU 42.5
- Price was: $265
- Price: $238.50
- Now 10% off is the current price
14

Burberry Patent Leather Chelsea Boots
Men's Size: 10 | EU 43
- Price was: $445
- Price: $356.00
- Now 20% off is the current price
24

Common Projects Suede Chelsea Boots
Men's Size: 10 | EU 43
Est. Retail $530
- Price was: $245
- Price: $220.50
- Now 10% off is the current price
21

Bottega Veneta Leather Chelsea Boots
Men's Size: 8.5 | EU 41.5
Est. Retail $1,540
- Price was: $535
- Price: $428.00
- Now 20% off is the current price
20

Versace Medusa Insignia Leather Chelsea Boots
Men's Size: 11.5 | EU 44.5
Est. Retail $1,370
- Price was: $410
- Price: $348.50
- Now 15% off is the current price
18

Common Projects Leather Chelsea Boots
Men's Size: 10 | EU 43
Est. Retail $560
- Price was: $175
- Price: $140.00
- Now 20% off is the current price
14

Officine Creative Leather Chelsea Boots
Men's Size: 8.5 | EU 41.5
Est. Retail $640
- Price was: $165
- Price: $148.50
- Now 10% off is the current price
11

AMI Leather Chelsea Boots
Men's Size: 10.5
- Price was: $295
- Price: $236.00
- Now 20% off is the current price
23

Blundstone Suede Chelsea Boots
Men's Size: 9
Est. Retail $220
- Price was: $155
- Price: $131.75
- Now 15% off is the current price
12

R.M. Williams Leather Chelsea Boots
Men's Size: 10.5
- Price was: $275
- Price: $233.75
- Now 15% off is the current price
11

Crockett & Jones Leather Chelsea Boots
Men's Size: 12
- Price was: $245
- Price: $220.50
- Now 10% off is the current price
9

Saint Laurent Leather Chelsea Boots
Men's Size: 10 | EU 43
Est. Retail $1,200
- Price was: $510
- Price: $459.00
- Now 10% off is the current price
7

The Kooples Suede Chelsea Boots
Men's Size: 9 | FR 42
- Price was: $85
- Price: $76.50
- Now 10% off is the current price
6

Shoto Leather Chelsea Boots
Men's Size: 10
- Price was: $135
- Price: $121.50
- Now 10% off is the current price
3

AMI Leather Chelsea Boots
Men's Size: 11
- Price was: $175
- Price: $157.50
- Now 10% off is the current price
15

Prada Leather Chelsea Boots
Men's Size: 11 | UK 10
- Price was: $145
- Price: $123.25
- Now 15% off is the current price
21

Louis Vuitton Leather Chelsea Boots
Men's Size: 9.5
- Price was: $325
- Price: $292.50
- Now 10% off is the current price
20

Common Projects Leather Chelsea Boots
Men's Size: 9 | EU 42
Est. Retail $620
- Price was: $185
- Price: $148.00
- Now 20% off is the current price
21

Gucci Leather Chelsea Boots
Men's Size: 9.5 | UK 9
- Price was: $285
- Price: $256.50
- Now 10% off is the current price
14

Gucci Web Accent Leather Chelsea Boots
Men's Size: 8 | UK 7.5
- Price was: $475
- Price: $427.50
- Now 10% off is the current price
12

Bottega Veneta Suede Chelsea Boots
Men's Size: 12.5 | EU 45.5
Est. Retail $950
- Price was: $265
- Price: $212.00
- Now 20% off is the current price
5

To Boot New York Suede Chelsea Boots
Men's Size: 8
- Price was: $75
- Price: $60.00
- Now 20% off is the current price
2

Camper Leather Chelsea Boots
Men's Size: 9
- Price was: $80
- Price: $68.00
- Now 15% off is the current price
22

Diemme Suede Chelsea Boots
Men's Size: 10 | EU 43
Est. Retail $350
- Price was: $135
- Price: $114.75
- Now 15% off is the current price
25

Prada Leather Chelsea Boots
Men's Size: 10.5 | UK 9.5
- Price was: $295
- Price: $236.00
- Now 20% off is the current price
20

Saint Laurent Suede Chelsea Boots
Men's Size: 8 | EU 41
Est. Retail $1,220
- Price was: $255
- Price: $204.00
- Now 20% off is the current price
7

J.M. Weston Leather Chelsea Boots
Men's Size: 8.5
- Price was: $255
- Price: $204.00
- Now 20% off is the current price
13

Tod's Suede Chelsea Boots
Men's Size: 8.5 | UK 7.5
- Price was: $80
- Price: $64.00
- Now 20% off is the current price
8

Tod's Leather Chelsea Boots
Men's Size: 12 | UK 11
- Price was: $90
- Price: $76.50
- Now 15% off is the current price
7

Hunter Rubber Rain Boots
Men's Size: 10 | US 10
- Price was: $115
- Price: $92.00
- Now 20% off is the current price
38

Marcell Von Berlin Denim Distressed Accents Chelsea Boots
Men's Size: 10
- Price was: $325
- Price: $260.00
- Now 20% off is the current price
33

Dolce & Gabbana Leather Chelsea Boots
Men's Size: 14
Est. Retail $1,140
- Price was: $410
- Price: $369.00
- Now 10% off is the current price
26

Dr. Martens Leather Chelsea Boots
Men's Size: 12
Est. Retail $230
- Price was: $95
- Price: $76.00
- Now 20% off is the current price
4

Bottega Veneta Leather Chelsea Boots
Men's Size: 11 | EU 44
Est. Retail $1,520
- Price was: $475
- Price: $380.00
- Now 20% off is the current price
41

Brunello Cucinelli Suede Chelsea Boots
Men's Size: 12 | EU 45
Est. Retail $1,200
- Price was: $510
- Price: $408.00
- Now 20% off is the current price
29

Tom Ford Patent Leather Chelsea Boots
Men's Size: 8.5
Est. Retail $1,580
- Price was: $445
- Price: $356.00
- Now 20% off is the current price
9

Sagmeister Leather Chelsea Boots
Men's Size: 12
- Price was: $115
- Price: $92.00
- Now 20% off is the current price
6

Fendi Zucca FF Logo Leather Chelsea Boots
Men's Size: 16
Est. Retail $1,420
- Price was: $385
- Price: $308.00
- Now 20% off is the current price
4

Neil Barrett Leather Chelsea Boots
Men's Size: 7 | EU 40
- Price was: $115
- Price: $92.00
- Now 20% off is the current price
2

Gucci Interlocking G Logo Leather Chelsea Boots
Men's Size: 9.5 | UK 9
- Price was: $595
- Price: $476.00
- Now 20% off is the current price
9

Bottega Veneta Suede Chelsea Boots
Men's Size: 11 | EU 44
Est. Retail $850
- Price was: $485
- Price: $388.00
- Now 20% off is the current price
19

Salvatore Ferragamo Leather Chelsea Boots
Men's Size: 8 | US 8
- Price was: $255
- Price: $204.00
- Now 20% off is the current price
10

Tod's Leather Chelsea Boots
Men's Size: 10.5 | UK 9.5
- Price was: $105
- Price: $84.00
- Now 20% off is the current price
7

Tom Ford Suede Chelsea Boots
Men's Size: 9
Est. Retail $1,580
- Price was: $595
- Price: $476.00
- Now 20% off is the current price
40

Marsèll Leather Chelsea Boots
Men's Size: 13
Est. Retail $900
- Price was: $310
- Price: $294.50
- Now 5% off is the current price
32

Prada Leather Distressed Accents Chelsea Boots
Men's Size: 9.5 | UK 8.5
- Price was: $275
- Price: $220.00
- Now 20% off is the current price
22

Bottega Veneta Rubber Rain Boots
Men's Size: 9 | EU 42
- Price was: $245
- Price: $196.00
- Now 20% off is the current price
17

Bottega Veneta Suede Chelsea Boots
Men's Size: 12 | EU 45
Est. Retail $970
- Price was: $245
- Price: $196.00
- Now 20% off is the current price
8

Saint Laurent Suede Chelsea Boots
Men's Size: 10 | EU 43
Est. Retail $1,110
- Price was: $310
- Price: $248.00
- Now 20% off is the current price
47

Ted Baker Leather Chelsea Boots
Men's Size: 12.5
Est. Retail $260
- Price was: $85
- Price: $68.00
- Now 20% off is the current price
4

Saint Laurent Suede Chelsea Boots
Men's Size: 10 | EU 43
Est. Retail $1,220
- Price was: $535
- Price: $428.00
- Now 20% off is the current price
32

Crockett & Jones Leather Chelsea Boots
Men's Size: 12
- Price was: $310
- Price: $248.00
- Now 20% off is the current price
12

Giorgio Armani Leather Chelsea Boots
Men's Size: 10
- Price was: $105
- Price: $84.00
- Now 20% off is the current price
10

Saint Laurent Leather Chelsea Boots
Men's Size: 12 | EU 45
Est. Retail $1,180
- Price was: $385
- Price: $308.00
- Now 20% off is the current price
27

Saint Laurent Suede Chelsea Boots
Men's Size: 12 | EU 45
Est. Retail $1,140
- Price was: $335
- Price: $268.00
- Now 20% off is the current price
18

Rag & Bone Suede Chelsea Boots
Men's Size: 10
- Price was: $65
- Price: $52.00
- Now 20% off is the current price
10

Saint Laurent Suede Chelsea Boots
Men's Size: 8 | EU 41
Est. Retail $1,110
- Price was: $345
- Price: $276.00
- Now 20% off is the current price
50

Saint Laurent Leather Chelsea Boots
Men's Size: 8 | EU 41
Est. Retail $1,200
- Price was: $510
- Price: $408.00
- Now 20% off is the current price
34

Tod's Leather Chelsea Boots
Men's Size: 10.5 | UK 9.5
- Price was: $95
- Price: $76.00
- Now 20% off is the current price
34

Salvatore Ferragamo Leather Chelsea Boots
Men's Size: 8.5 | US 8.5
- Price was: $95
- Price: $76.00
- Now 20% off is the current price
8

Loro Piana Leather Chelsea Boots
Men's Size: 12
Est. Retail $1,680
- Price was: $455
- Price: $364.00
- Now 20% off is the current price
26

Prada Leather Chelsea Boots
Men's Size: 10 | UK 9
- Price was: $285
- Price: $228.00
- Now 20% off is the current price
20

Aubercy Leather Chelsea Boots
Men's Size: 13
- Price was: $255
- Price: $204.00
- Now 20% off is the current price
5

Burberry House Check Pattern Leather Chelsea Boots
Men's Size: 9 | EU 42
- Price was: $365
- Price: $292.00
- Now 20% off is the current price
27

Alexander McQueen Leather Chelsea Boots
Men's Size: 14 | EU 47
Est. Retail $1,000
- Price was: $365
- Price: $328.50
- Now 10% off is the current price
24

Givenchy Leather Chelsea Boots
Men's Size: 10 | EU 43
Est. Retail $1,060
- Price was: $255
- Price: $204.00
- Now 20% off is the current price
45

Mezlan Leather Chelsea Boots
Men's Size: 11.5
Est. Retail $1,600
- Price was: $485
- Price: $388.00
- Now 20% off is the current price
10

Thom Browne Patent Leather Chelsea Boots
Men's Size: 7.5
- Price was: $375
- Price: $300.00
- Now 20% off is the current price
21

Hunter Rubber Rain Boots
Men's Size: 10 | US 10
- Price was: $115
- Price: $92.00
- Now 20% off is the current price
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