Home / Men's Dress Shoes
Show Sidebar

Style

Men's Dress Shoes

Many under estimate the power of a good dress shoe. Heel Boy understands that not every men's dress shoe is built alike and so we fill our collection with the widest of variety. Check out styles like sleek and simple or wing tipped and brogue'd from brands like Cole Haan, Rockport, Dockers and others.
Grid view List view
products/WILLIAMCIIA0067_SID.jpg
products/WILLIAMCIIA0067.jpg
Quick View
Cole Haan Men
Cole Haan Men's Williams Cpt Ii British Tan-C12337 M

$270.00

products/WARREN_20CAPA0090_SID.jpg
products/WARREN_20CAPA0090.jpg
Quick View
Cole Haan Men
Cole Haan Men's Warren Cap Ox Black-C20155 M

$270.00

products/WATSONA1233_SID.jpg
products/WATSONA1233.jpg
Quick View
Cole Haan Men
Cole Haan Men's Watson Cap Toe C26146/British Tan/Lea M

$350.00

products/GRAMERCYA1808_SID.jpg
products/GRAMERCYA1808.jpg
Quick View
Cole Haan Men
Cole Haan Men's Gramercy Wholecut Dress Ox Brown M

$350.00

products/WASHINGTONA0595_SID_fc192451-35ab-4198-b225-d96c83f8caeb.jpg
products/WASHINGTONA0595_02c5ecb3-c5fc-491f-8265-aff6ed736a2b.jpg
Quick View
Cole Haan Men
Cole Haan Men's Washington Grand Laser Wing Ox Lzr Wg Ox/Brit Tan Lava-C24523 M

$395.00

products/WASHINGTONA0594_SID_8496afd5-2798-4136-8d4c-9cce06762cdc.jpg
products/WASHINGTONA0594_f8faa1d4-d543-4b35-96e2-35e78002c98b.jpg
Quick View
Cole Haan Men
Cole Haan Men's Washington Grand Laser Wing Ox Lzr Wg Ox/Black/Blue-C23999 M

$395.00

products/HARRISONA0397_SID.jpg
products/HARRISONA0397.jpg
Quick View
Cole Haan Men
Cole Haan Men's Harrison Grand Short Wing Ox British Tan/Dk Natural-C24168 M

$295.00

products/HARRISONA0397_SID_fecf83db-d8f7-4bd6-849e-d045f95ce535.jpg
products/HARRISONA0397_f92eacf8-b72f-49b3-affc-236da5b9ddba.jpg
Quick View
Cole Haan Men
Cole Haan Men's Harrison Grand Short Wing Ox British Tan/Dk Natural-C24168 W

$295.00

products/WILLIAMSA0343_SID.jpg
products/WILLIAMSA0343.jpg
Quick View
Cole Haan Men
Cole Haan Men's Williams Wing Ii Black-C12209 M

$320.00

products/WASHINGTONA1239_SID_d6298f9f-8002-4f56-8c67-c1375f9587a2.jpg
products/WASHINGTONA1239_6d519597-46f9-4f3b-9b3d-c22495188ecd.jpg
Quick View
Cole Haan Men
Cole Haan Men's Washington Grd Whole Cut C26589/British Tan M

$395.00

products/WASHINGTONA1238_SID_07049e40-d3ee-478f-9f52-72fea7380698.jpg
products/WASHINGTONA1238_FID_a28cfd82-1484-4e8c-88dd-55cdbc91f231.jpg
Quick View
Cole Haan Men
Cole Haan Men's Washington Grd Whole Cut C26588/Black M

$395.00

products/WILLIAMS_20PA0073_SID_7a66ed31-c7c5-459a-b5c5-5d3fb6402a13.jpg
products/WILLIAMS_20PA0073_295480f2-ed5a-4ad8-a4fb-ecd201d42b17.jpg
Quick View
Cole Haan Men
Cole Haan Men's Williams Plain Ox Waxy Casual Leather-C12203 M

$300.00

products/LEWISA2108_SID.jpg
products/LEWISA2108.jpg
Quick View
Cole Haan Men
Cole Haan Men's Lewis Grand Plain Toe Ox Black M

$250.00

products/dm-orso-black-2.jpg
products/dm-orso-black.jpg
Quick View
Dockers
Dockers Men's Orso Dress Shoe in Black

$130.00

products/dockers-garfield-black-4.jpg
products/dockers-garfield-black.jpg
Quick View
Dockers
Dockers Men's Garfield Shoe in Black

$99.99

products/dockers-hawley-black-04.jpg
products/dockers--hawley-black-01.jpg
Quick View
Dockers
Dockers Men's Hawley Dress Shoe in Black

$140.00

products/dockers-hawley-brown-04.jpg
products/dockers--hawley-brown-1.jpg
Quick View
Dockers
Dockers Men's Hawley Dress Shoe in Dark Tan

$140.00

products/rs11980_shane_drkbrn_sdr-lpr.jpg
products/rs12223_shane_drkbrn_pri-lpr.jpg
Quick View
Vionic
Vionic Men's Shane Lace Up in Dark Brown

$194.95

products/WARREN_20CAPA0099_SID.jpg
products/WARREN_20CAPA0099.jpg
Quick View
Cole Haan Men
Cole Haan Men's Warren Cap Ox British Tan-C20153 M

$270.00

products/WARREN_20CAPA0090_SID_482c2dfb-2111-45d5-a230-9fe87e1067b9.jpg
products/WARREN_20CAPA0090_f1fc448d-076a-4071-be06-129659e07c6d.jpg
Quick View
Cole Haan Men
Cole Haan Men's Warren Cap Ox Black-C20155 W

$270.00

products/HENRYA0626_SID.jpg
products/HENRYA0626.jpg
Quick View
Cole Haan Men
Cole Haan Men's Henry Grand Cap Toe British Tan/Dark Natura-C24519 M

$250.00

products/HENRYA0627_SID.jpg
products/HENRYA0627.jpg
Quick View
Cole Haan Men
Cole Haan Men's Henry Grand Cap Toe Black/Black-C24518 M

$250.00

products/rs11984_sullivan_brn_sdr-lpr.jpg
products/rs12235_sullivan_brn_pri-lpr.jpg
Quick View
Vionic
Vionic Men's Sullivan Slip On in Brown

$194.95

products/rs11985_sullivan_tpe_sdr-lpr_186149d5-a3c8-43e4-b67f-adf4349630d3.jpg
products/rs12236_sullivan_tpe_pri-lpr_2674683a-ef9e-4f23-89e4-a17f3845b759.jpg
Quick View
Vionic
Vionic Men's Sullivan Slip On in Taupe

$194.95

products/rs11983_sullivan_blk_sdr-lpr.jpg
products/rs12234_sullivan_blk_pri-lpr.jpg
Quick View
Vionic
Vionic Men's Sullivan Slip On in Black

$194.95

products/dm-geary-black-3_b5ea5982-a495-4a3e-a41d-2ef6b70d3847.jpg
products/dm-geary-black-0_a16b0214-3e2f-475a-a884-80291b8d92ba.jpg
Quick View
Dockers
Dockers Men's Geary Loafer in Black

$120.00

products/BX2410A0051_SID.jpg
products/BX2410A0051.jpg
Quick View
Rockport Men
Rockport Men's Plain Toe Black M

$150.00

products/BX2410A0051_SID_66c3bc03-8572-4d3d-a501-d355a635e432.jpg
products/BX2410A0051_24056b57-06fe-4b74-8714-dfe393b9744b.jpg
Quick View
Rockport Men
Rockport Men's Plain Toe Black W

$150.00

products/BX2410A0051_SID_4988b379-e044-4882-8e92-4d5d39d3aefb.jpg
products/BX2410A0051_479ca2b8-373a-4ab1-ac0e-3bdf0872ba84.jpg
Quick View
Rockport Men
Rockport Men's Plain Toe Black W

$150.00

products/rs8779_555bruno_blk_sdr-lpr_e0d9170a-747b-4df1-8c78-58be21629b1e.jpg
products/rs9587_555bruno_blk_pri-lpr_3ebdb15b-61cb-4b4c-a685-98f87dfe09bc.jpg
Quick View
Vionic
Vionic Men's Bruno Oxford in Black

$194.95

Kenneth Cole Men's Klay Lace Up Oxfords in Cognac
Quick View
Kenneth Cole
Kenneth Cole Men's Klay Lace Up Oxfords in Cognac

$135.00

Kenneth Cole Men's Klay Lace Up Oxfords in Black
Quick View
Kenneth Cole
Kenneth Cole Men's Klay Lace Up Oxfords in Black

$135.00

products/FEATHERA1846_SID.jpg
products/FEATHERA1846.jpg
Quick View
Cole Haan Men
Cole Haan Men's Feathercraft Grd Venetian Brown M

$250.00

products/FEATHERA1845_SID_be7b7c52-b908-448a-ac6f-5aeb8a0a872e.jpg
products/FEATHERA1845_97d49488-c944-4899-84fa-11e770ae9c9b.jpg
Quick View
Cole Haan Men
Cole Haan Men's Feathercraft Grd Venetian Black M

$250.00

products/M77066A0020_SID.jpg
products/M77066A0020_f993cc6c-d27c-46f8-85f1-fbff5fbc1db6.jpg
Quick View
Rockport Men
Rockport Men's Cap Toe Brown W

$150.00

products/V73839A0008_SID_8da4d220-656c-47bb-8b55-6c0a3450e469.jpg
products/V73839A0008_83a3e678-9142-4c24-b7e5-6c027887f276.jpg
Quick View
Rockport Men
Rockport Men's Wp Cptoe Black M

$155.00

products/V73839A0008_SID_6de38096-9e3a-4840-9c9e-269422bc788b.jpg
products/V73839A0008_715e603e-bf3d-47f9-bed4-0e3cefc98899.jpg
Quick View
Rockport Men
Rockport Men's Wp Cptoe Black W

$155.00

products/V73839A0008_SID.jpg
products/V73839A0008.jpg
Quick View
Rockport Men
Rockport Men's Wp Cptoe Black Xw

$155.00

products/W_20ORIGINALA1024_SID_417f3ed2-9afc-421e-9653-3578b1eb51f9.jpg
products/W_20ORIGINALA1024_6863094e-4600-453f-b8b6-a7a0dca67036.jpg
Quick View
Cole Haan Men
Cole Haan Men's W. Original Grd Wgtp Ox C26471/Woodbury/Lea/Ivory M

$200.00

products/W_20ORIGINALA0994_SID.jpg
products/W_20ORIGINALA0994.jpg
Quick View
Cole Haan Men
Cole Haan Men's W. Original Grd Wgtp Ox C26472/Woodbury/Java M

$200.00

products/W_20ORIGINALA1021_SID_92297b03-7797-4f71-bd5d-8df5ea68b21c.jpg
products/W_20ORIGINALA1021_3fa48ef1-c531-4b2c-9be8-a601c77264a6.jpg
Quick View
Cole Haan Men
Cole Haan Men's W. Original Grd Wgtp Ox C26470/Black/Lea/Ironstone M

$200.00

products/dm-reliant-brown-1.jpg
products/dm-reliant-brown.jpg
Quick View
Dockers
Dockers Men's Reliant Dress Shoe in Brown

$110.00

products/dm-reliant-black-1.jpg
products/dm-reliant-black.jpg
Quick View
Dockers
Dockers Men's Reliant Dress Shoe in Black

$110.00

products/dm-prosperity-black-1_d0d5988b-3e34-4dd0-b6de-0feff5a06259.jpg
products/dm-prosperity-black_bde54243-0c3e-4ae3-86c3-b30b541be09a.jpg
Quick View
Dockers
Dockers Men's Prosperity Dress Shoe in Black

$130.00

products/worden_01_320112_01.jpg
products/worden_01_320112_00.jpg
Quick View
Dockers
Dockers Men's Worden Dress Shoe in Black

$99.99

products/kennethcole_20design_20213081_204_0f2e2c73-7f37-43ec-a23b-c4ee47a24e48.jpg
products/kennethcole_20design_20213081_203_38d50b9f-ab38-4820-96fd-396f449edf41.jpg
Quick View
Kenneth Cole
Kenneth Cole Men's DESIGN 213081 Oxfords in Cognac

$110.00

products/stevemadden_m_driscoll_tan.jpg
products/stevemadden_m_driscoll_tan2.jpg
Quick View
STEVE MADDEN
Steve Madden Men's Driscoll in Tan

$150.00

Also Available In-Store

products/tb_m_fontann_black.jpg
products/tb_m_fontann_black2.jpg
Quick View
TED BAKER
Ted Baker Men's Fonntan in Black

$320.00

Also Available In-Store

products/stevemadden_m_junno_black_27628457-d40a-4c5d-92d3-a7c4efd645cc.jpg
products/stevemadden_m_junno_black2_7e84d4c7-0d44-4124-af0d-d5ddb8516d76.jpg
Quick View
STEVE MADDEN
Steve Madden Men's Junno in Black

$160.00

Also Available In-Store

products/logan_blk_01_zpszo0h9d0y.jpg
products/logan_blk_2_zpsvmviayv6.jpg
Quick View
G.H Bass & Co.
G.H Bass & Co. Men's Logan in Black

$185.00

Also Available In-Store

products/larson_blk_1_zpsnong937t.jpg
products/larson_2_blk_zpsuslu2ae9.jpg
Quick View
G.H Bass & Co.
G.H Bass & Co. Men's Larson in Black

$185.00

Also Available In-Store

products/dm-corinth-brown-2.jpg
products/dm-corinth-brown-1.jpg
Quick View
Dockers
Dockers Men's Corinth Oxford in Cognac

$140.00

products/dockers--benfield-black-04.jpg
products/dockers--benfield-black-01.jpg
Quick View
Dockers
Dockers Men's Benfield Oxford in Black

$149.99

products/dm-robertson-brn04.jpg
products/dm-robertson-brn01.jpg
Quick View
Dockers
Dockers Men's Robertson Dress Shoe in Chilie

$119.99

products/dm-robertson-blk04_d9d96315-0c06-42f9-b8b0-7a12f4988931.jpg
products/dm-robertson-blk01_b087f93f-11ab-4762-8f3e-71e9df9c0f24.jpg
Quick View
Dockers
Dockers Men's Robertson Dress Shoe in Black

$119.99

products/V76115A0008_SID_d35b4e2a-cd50-4d8f-94cf-ea3076cc29aa.jpg
products/V76115A0008_56cc4ca8-7a78-40be-a1fc-7df72561bc1d.jpg
Quick View
Rockport Men
Rockport Men's Wp Plain Black M

$145.00

products/V76115A0008_SID.jpg
products/V76115A0008.jpg
Quick View
Rockport Men
Rockport Men's Wp Plain Black W

$145.00

products/CH1235A0008_SID.jpg
products/CH1235A0008.jpg
Quick View
Rockport Men
Rockport Men's Plain Toe Black M

$150.00

products/CH1235A0008_SID_d2675959-7105-4633-a7d8-47fe8b4adeaf.jpg
products/CH1235A0008_04e94caf-da86-41ba-addf-ac9895824925.jpg
Quick View
Rockport Men
Rockport Men's Plain Toe Black W

$150.00

products/V81485A0105_SID_97a71d47-b8e0-4c66-9b47-ec68b843be28.jpg
products/V81485A0105_00b200cd-5fcc-4e44-99e7-9a68f9851377.jpg
Quick View
Rockport Men
Rockport Men's Apron Brown M

$145.00

products/V81485A0105_SID_8582494e-fe66-4fdd-8a65-3caba29b2650.jpg
products/V81485A0105_9fe9e274-2903-4f19-b819-afb66816a991.jpg
Quick View
Rockport Men
Rockport Men's Apron Brown W

$145.00

products/H79736A0008_SID_827a0525-6b95-4a82-8d10-8caa781024f5.jpg
products/H79736A0008_17f13b75-649c-4655-b282-0bdf98c85164.jpg
Quick View
Rockport Men
Rockport Men's Apron Toe Black M

$165.00

products/H79736A0008_SID_8a06d0e4-cd56-47a9-aa2d-5270bf0fdfd7.jpg
products/H79736A0008_09c9a149-e8b3-4b7b-b9c8-88f697d87d4e.jpg
Quick View
Rockport Men
Rockport Men's Apron Toe Black W

$165.00

products/FRANKLANDA2035_SID.jpg
products/FRANKLANDA2035.jpg
Quick View
Cole Haan Men
Cole Haan Men's Frankland Grand Plain Toe Ox Brown M

$250.00

products/LEWISA2106_SID_772a42e3-57b7-4eb5-9a7d-ede43c80c9db.jpg
products/LEWISA2106_f3bccfc0-cfc7-44af-82b6-e016e4af2d0c.jpg
Quick View
Cole Haan Men
Cole Haan Men's Lewis Grand Plain Toe Ox Brown M

$250.00

products/WARNERA1962_SID_3e2b0838-4dc0-4e72-b059-acd97f4563c8.jpg
products/WARNERA1962_ea16271c-287e-4aa5-83c0-43a2e6a5e6ca.jpg
Quick View
Cole Haan Men
Cole Haan Men's Warner Grnd Monk Brown M

$350.00

products/WILLIAMCIIA0068_SID.jpg
products/WILLIAMCIIA0068.jpg
Quick View
Cole Haan Men
Cole Haan Men's Williams Cpt Ii Black/Leather-C12202 M

$300.00

products/V73841A0008_SID_81b7ebd3-5216-4f6b-8ef4-fc1250535562.jpg
products/V73841A0008_ffe3191e-3520-4780-bcdb-047460eb5234.jpg
Quick View
Rockport Men
Rockport Men's Wp Aprn Black M

$145.00

products/V73841A0008_SID_b9f2a5c2-bc4d-4f31-8f63-4031cb2803ad.jpg
products/V73841A0008_fc27031e-ae25-4549-9fd0-ba87ead6ebed.jpg
Quick View
Rockport Men
Rockport Men's Wp Aprn Black W

$145.00

products/V80544A0008_SID_836ed351-b168-42e4-adeb-f95795c3a9cb.jpg
products/V80544A0008_e178bbe3-1c61-4aa7-a640-4d6db81aaaf1.jpg
Quick View
Rockport Men
Rockport Men's Bike Ox Black M

$140.00

products/V80544A0008_SID_2044f207-757d-46a2-a1de-4284686d630c.jpg
products/V80544A0008.jpg
Quick View
Rockport Men
Rockport Men's Bike Ox Black W

$140.00

products/dm-exchange-black-2.jpg
products/dm-exchange-black-1.jpg
Quick View
Dockers
Dockers Men's Exchange Dress Shoe in Black

$110.00

products/dm-gordon-black-1_f6885214-6593-4094-8fb8-a164d44b17a9.jpg
products/dm-gordon-black_3f4309d8-e408-417e-9a17-40513c9c104c.jpg
Quick View
Dockers
Dockers Men's Gordon Dress Shoe in Black

$110.00

products/dm-endow-black-1.jpg
products/dm-endow-black.jpg
Quick View
Dockers
Dockers Men's Endow Oxford in Black

$130.00

products/dm-endow-black-1_96e3384d-6a58-46b4-82a9-11381e340b0d.jpg
products/dm-endow-black_0ed4cb90-94f9-4785-96c2-6457f4568ab6.jpg
Quick View
Dockers
Dockers Men's Endow Oxford in Black (Wide)

$130.00

products/dm-franchise-black_0e903569-50c5-4f51-a563-04aaaf2d8cdc.jpg
products/dm-franchise-black-4_4221a73a-b4b3-4eab-a004-ae19ec92ca73.jpg
Quick View
Dockers
Dockers Men's Franchise Loafer in Black

$130.00

Showing: 1 - 76 of 143

Recently Viewed Products