Men's Flat Caps & Ivy Caps

Clean lines and tailored panels characterize the styles found in this selection, offering flat caps crafted for comfort and understated sophistication. Depending on availability, designs may feature classic wool blends, lightweight fabrics, textured patterns, or modern interpretations shaped with attention to fit. Within this collectoin you’ll find pieces suited for everyday wear, seasonal transitions, and refined casual dressing across the Hats.com collection. Other throwback styles include Men's Pork Pie Hats and Men's Fedoras. 
  • Image of Clave Cap product
    25% off
    Bailey 1922

    Clave Cap

    $85.00 $63.75
    2 colors
  • Image of Hawley Cap product
    25% off
    Bailey 1922

    Hawley Cap

    $90.00 $67.50
    2 colors
  • Image of Newry Cap product
    Bailey 1922

    Newry Cap

    $80.00
    2 colors
  • Image of Roan Cap product
    25% off
    Bailey 1922

    Roan Cap

    $85.00 $63.75
    3 colors
  • Image of Rankin Dockman Cap product
    25% off
    Bailey 1922

    Rankin Dockman Cap

    $85.00 $63.75
    2 colors
  • Image of Penner Contour Cap product
    Bailey 1922

    Penner Contour Cap

    $85.00
    2 colors
  • Image of Cassell Newsboy Cap product
    Bailey 1922

    Cassell Newsboy Cap

    $70.00
    2 colors
  • Image of Wickes Flat Cap product
    Bailey 1922

    Wickes Flat Cap

    $75.00
    2 colors
  • Image of Chadwick Dockman Cap product
    Bailey 1922

    Chadwick Dockman Cap

    $70.00
    2 colors
  • Image of Heathered Tie Dye 504 product
    🇺🇸
    Kangol

    Heathered Tie Dye 504

    $65.00
    3 colors
  • Image of Rainbow Ventair 504 Flat Cap product
    Kangol

    Rainbow Ventair 504 Flat Cap

    $70.00
    1 color
  • Image of Bermuda Hawker product
    Kangol

    Bermuda Hawker

    $80.00
    2 colors

Frequently Asked Questions about Men's Flat Caps & Ivy Caps

What types of men's flat caps are available?

Ivy caps (sleek, single-panel), newsboy caps (fuller, multi-panel), Greek fisherman caps (structured with a hard brim), and various panel configurations. Each has a different personality and fits different style preferences.

What flat cap material is best for men?

Wool and tweed for fall/winter classic and warm. Cotton and linen for spring/summer light and breathable. Leather for year-round edge. Polyester blends for durability and easy care.

How should a men's flat cap fit?

Level on your head with the brim just above your eyebrows. The crown should conform to your head shape without bulging. Flat caps come in specific sizes measure your head and check the sizing chart.

Can men wear flat caps to the office?

In creative and business-casual environments, absolutely. A quality wool or tweed flat cap with a sport coat is a polished, intentional look. In conservative corporate settings, remove it indoors.

What age range suits flat caps for men?

All ages that's the beauty of flat caps. They suit men in their 20s through their 80s. Younger men tend to wear them with casual outfits; older men often pair them with more tailored looks. It's a genuinely ageless hat.