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Wingtip Shoes

Whether you’re dressing up or down, kick your outfits into high gear with wing-tip shoes. From dress shoes to more casual styles, give your look a dapper touch with this classic design.

Just Wing It
Give your workweek wardrobe a tailored element. Check out dress shoes like oxfords and loafers featuring this unique perforated detail at the toe. Classic must-haves for your shoe collection? Black and brown leather styles from Steve Madden, Alfani and Florsheim. For a distinct shine, try a pair in patent leather. For a more worn and warm style, suede shoes in cognac, tan—or even green and blue hues. Going ultra modern with your office outfits? Two-toned lace-ups from Stacy Adams are the way to go.

Dapper Dude
Elevate your off-the-clock looks with wing-tip casual shoes. A laid-back outfit of jeans and a button-front gets the perfect finishing touch from lace-ups from Rockport, Sebago and Kenneth Cole. Or go for the stylish functional appeal of brogue meets rugged with oxfords featuring weatherproof exteriors and lug outsoles for extra traction.

Shopping for new shoes? Macy’s offers an extensive selection of men’s shoes including wing-tip designs and much more. Don’t forget to check out our extended sizes for wide-width and narrow-width footwear.

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  • 31 items in Wingtip Shoes

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    • 3 colors
      Cole Haan Men's Original Grand Wing Oxfords
      $150.00
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    • 2 colors
      Extended Widths
      Stacy Adams Men's Garrison Wing-Tip Oxford
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      $90.00
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    • 3 colors
      Extended Widths
      Stacy Adams Men's Dunbar Wingtip Oxfords
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      $95.00
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      (74)
    • 2 colors
      Extended Widths
      Rockport Men's Style Purpose Wingtip Oxfords
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      $125.00
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      (86)
    • Ecco Men's Jeremy Wingtip Hybrid Oxfords
      $150.00
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    • 2 colors
      Cole Haan Men's Henry Grand Short Wing-Tip Oxfords
      $170.00
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    • 4 colors
      Stacy Adams Men's Kemper Wingtip Oxfords
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      $95.00
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    • Extended Widths
      Florsheim Men's Lexington Kiltie Tasseled Wing-Tip Loafer
      $110.00
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      (119)
    • 2 colors
      Extended Widths
      Johnston & Murphy Men's Conard Wing Tip Oxford
      $159.00
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    • 2 colors
      Extended Widths
      Florsheim Men's Lexington Wing-Tip Oxford
      $110.00
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    • 2 colors
      Johnston & Murphy Men's Fletcher Wingtip Lace-Up Oxfords
      $149.00
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    • Stacy Adams Men's Ansley Wingtip Oxfords
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      $100.00
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      (4)
    • 2 colors
      Cole Haan Men's Washington Grand Casual Wingtip Oxfords
      $400.00
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    • Extended Widths
      Florsheim Men's Castellano Wing-Tip Oxfords
      $130.00
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      (183)
    • Stacy Adams Dayton Wing-Tip Lace-Up Shoes
      $100.00
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      (91)
    • Johnston & Murphy Men's Tabor Wing Tip Oxfords
      $135.00
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      (7)
    • Extended Widths
      Rockport Men's Style Purpose Wingtip Blucher Oxfords
      Limited-Time Special
      $130.00
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      (2)
    • Kenneth Cole Reaction Men's Klay Double-Monk Strap Oxfords
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      $125.00
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    • Johnston & Murphy Men's Hernden Perforated Wingtip Lace-Up Oxfords
      Everyday Value
      $129.98
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    • Extended Widths
      Rockport Men's Total Motion Sport Dress Wingtip Oxfords
      $130.00
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      (1)
    • Extended Widths
      Rockport Men's Essential Details II Wing Tip Waterproof Oxford
      $110.00
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      (54)
    • Extended Widths
      Rockport Men's Total Motion Sport Dress Perforated Wingtip Oxfords
      $140.00
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    • 2 colors
      Dockers Men's Monticello Perforated Oxfords
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      $90.00
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    • 2 colors
      Born Men's Bearse Knit Lace-Up Wingtip Oxfords
      $95.00
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    • Extended Widths
      Florsheim Brookside Wing-Tip Oxfords
      $100.00
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      (7)
    • Extended Widths
      Florsheim Men's Castellano Wing-Tip Oxfords
      $130.00
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      (112)
    • G.H. Bass & Co. Men's Clinton Wing-Tip Oxfords
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      $110.00
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    • 2 colors
      Donald Pliner Men's Sennet Dipped Calf Oxfords
      $175.00
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    • Massimo Emporio Men's Cap-Toe Brogue Oxfords, Created for Macy's
      $395.00
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    • Mezlan Men's Short Wing Patent Blucher Oxfords, Created for Macy's
      $275.00
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    • Donald Pliner Men's Sennet Calf Suede Oxfords
      $175.00
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    • Showing All 31 Items