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There comes a time in every guy’s life (aka, a new season) when it’s time to swap those beloved sneakers for something a bit more stylized. Fret not. These boots, oxfords, chukkas and more are just as comfortable as your dependable kicks yet they give the jeans and button-down formula a much-needed injection of sophistication. Pair any of these styles with cuffed chinos and a button-down for a foolproof look this fall and winter. The Details: Brands include ksubi, Sebago, Tretorn and more.
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JD Fisk Men’s Drew Boot (Brown)$229$75.00 -
JD Fisk Men’s Pete Boot (Brown)$179$75.00 -
True Religion Men’s Dan Boot (Black)$150$121.00 -
True Religion Men’s Dan Boot (Dark Brown)$150$121.00 -
J Artola Men’s Alan Boot (Bark)$395$121.00 -
J Artola Men’s Alan Boot (Black)$395$121.00 -
J Artola Men’s Atlas Boot (Black)$395$75.00 -
J Artola Men’s Atlas Boot (Dark Brown)$395$70.00 -
Timberland Abington Men’s 5$240$70.00 -
Timberland Abington Men’s 7-Eye Ankle Boot (Black)$180$55.00 -
Timberland Abington Men’s 7-Eye Ankle Boot (Light Brown)$180$75.00 -
Timberland Abington Men’s Desert Boot (Light Brown)$165$70.00 -
Timberland Abington Men’s Farmer Boot (Light Brown)$200$70.00 -
Timberland Abington Men’s Hiker GTX (Black)$200$70.00 -
Timberland Abington Men’s Hiker GTX (Light Brown)$200$75.00 -
Timberland Abington Men’s Hiker GTX (Grey Suede)$200$70.00 -
Timberland Abington Men’s Logger Boot (Dark Brown)$240$95.00 -
Timberland Boot Company Men’s Counterpane Venetian Loafer (Dark Brown)$250$85.00 -
Timberland Men’s Takhead Patch Boot (Medium Brown)$395$80.00 -
Timberland Boot Company Men’s Counterpane Spectator Oxford (Granite Greige/Tan)$250$80.00 -
Timberland Boot Company Men’s Counterpane Spectator Oxford (Tobacco/Brown Suede)$250$85.00 -
Timberland Men’s Mudlark Safari Chukka Boot (Fox Brown)$295$95.00 -
Timberland Men’s Tackhead 6$350$91.00 -
Timberland Men’s Tackhead 6$350$82.00 -
Timberland Men’s Tackhead Chukka Boot (Medium Brown)$360$69.00 -
Timberland Men’s Takhead Pull-On Boot (Brown/Olive)$395$126.00 -
Rogue Men’s Guada Burnished Boot (Dark Taupe)$350$126.00 -
Rogue Men’s Randy Boat Shoe Chukka (Navy blue)$285$126.00 -
SeaVees Men’s Hiker Boot (Dark Earth)$155$144.00 -
ksubi Men’s Buckley 1 Cap Toe Oxford (Beige)$420$174.00 -
ksubi Men’s Buckley 1 Cap Toe Oxford (Black)$420$147.00 -
ksubi Men’s Buckley 1 Cap Toe (Brown)$420$147.00 -
ksubi Men’s Buckley 5 Boot (Brown Vachetta)$483$150.00 -
ksubi Men’s Buckley 6 Boot (Tan)$580$156.00 -
ksubi Men’s Cast Canvas Oxford (Khaki)$490$141.00 -
ksubi Men’s Cast Canvas Oxford (Navy)$490$141.00 -
ksubi Men’s Cast Oxford (Brown)$500$151.00 -
ksubi Men’s Jacob Lo Boot (Brown)$520$62.00 -
ksubi Men’s Lambert 1 Lo Boot (Beige)$470$58.00 -
ksubi Men’s Lambert 1 Lo Boot (Tan)$470$64.00 -
ksubi Men’s Lambert 2 Boot (Brown Rustico)$505$64.00 -
Swear Men’s Lou 4 Shoe (Oxblood)$198$35.00 -
Sebago Men’s Filson Beacon Chukka (Dark Brown)$165$35.00 -
Sebago Men’s Kettle Boot (Luggage Tan)$175$49.00 -
Sebago Men’s Kettle Boot (Rich Brown)$175$49.00 -
Tretorn Men’s Strala Boot (Brown/Gum)$65$49.00 -
Tretorn Men’s Strala Boot (Olive/Gum)$65$49.00 -
Tretorn Men’s Krona Mid Leather Chukka Sneaker (Balsam Green)$100$79.00 -
Tretorn Men’s Krona Mid Leather Chukka Sneaker (Sailing Grey)$100$79.00 -
Tretorn Men’s Krona Mid Leather Chukka Sneaker (Sundown Brown)$100$ -
Tretorn Men’s Sub Winter Rain Boot (Black/Grey)$80$ -
Tretorn Men’s Klipporone Combo Boot (Spice Brown/Capers)$140$ -
Tretorn Men’s Klipporone Lace-Up Boot (Black/Fiery Red)$140$
