Skip to content
Free Shipping in Canada with purchases over $125
Free Shipping in Canada with purchases over $125

The Tailored Sportsman

THE TAILORED SPORTSMAN™ has been the benchmark of show ring quality and style for decades. Renowned for classic tailoring and premium fabrics, the apparel creates an impeccable presentation instantly recognizable by discerning equestrians everywhere. Stylish touches and updated colors keep the timeless looks fresh.

Filters

$
$
Tailored Sportsman Icefil Long Sleeve- DIRT ROAD - Vision Saddlery
Tailored Sportsman Icefil Long Sleeve- DIRT ROAD - Vision Saddlery Sale Sale

CLEARANCE-Tailored Sportsman Icefil Long Sleeve- DIRT ROAD

$109.95
$109.95 - $109.95
$109.95
$87.96
$87.96 - $87.96
$87.96

FINAL SALE The Tailored Sportsman Ice Fil Shirt is the stylish way to keep your cool this season! The fabric is moisture-wicking and fast dryi...

View full details
$109.95
$109.95 - $109.95
$109.95
$87.96
$87.96 - $87.96
$87.96
Sale Sale
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - Pinkberry/Tan - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - Pinkberry/Tan - Vision Saddlery Sale Sale

* CLEARANCE* Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - Pinkberry/Tan

$279.00
$279.00 - $279.00
$279.00
$269.00
$269.00 - $269.00
$269.00

The Mid Rise is 1″ higher in the rise than its Low Rise counterpart. The Tailored Sportsman name is synonymous with quality and classic style. The ...

View full details
$279.00
$279.00 - $279.00
$279.00
$269.00
$269.00 - $269.00
$269.00
Sale Sale
Tailored Sportsman Icefil Long Sleeve- Almost Pink - Vision Saddlery

Tailored Sportsman Icefil Long Sleeve- Almost Pink

$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

FINAL SALE The Tailored Sportsman Ice Fil Shirt is the stylish way to keep your cool this season! The fabric is moisture-wicking and fast dryi...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Tailored Sportsman Icefil Long Sleeve- Shadow - Vision Saddlery

Tailored Sportsman Icefil Long Sleeve- Shadow

$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

*These products are price controlled by the supplier/ distributor. The Tailored Sportsman Ice Fil Shirt is the stylish way to keep your cool t...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - BLUEST BLUE/TAN - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - BLUEST BLUE/TAN - Vision Saddlery

Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - BLUEST BLUE/TAN

$279.00 - $279.00
$279.00
$295.00
$295.00 - $295.00
$295.00

The Mid Rise is 1″ higher in the rise than its Low Rise counterpart. The Tailored Sportsman name is synonymous with quality and classic style. The ...

View full details
$279.00 - $279.00
$279.00
$295.00
$295.00 - $295.00
$295.00
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - SHADOW/TAN - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - SHADOW/TAN - Vision Saddlery

Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - SHADOW/TAN

$295.00 - $295.00
$295.00
$295.00 - $295.00
$295.00

The Mid Rise is 1″ higher in the rise than its Low Rise counterpart. The Tailored Sportsman name is synonymous with quality and classic style. The ...

View full details
$295.00 - $295.00
$295.00
$295.00 - $295.00
$295.00
Tailored Sportsman Ladies Tech Light Mid Rise Silicone Knee Breech - ESPRESSO - Vision Saddlery

Tailored Sportsman Ladies Tech Light Mid Rise Silicone Knee Breech - ESPRESSO

$339.95 - $339.95
$339.95
$339.95 - $339.95
$339.95

The Tailored Sportsman Ladies Tech Light Mid Rise Silicone Knee Breech combines advanced Tech Light fabric with silicone knee patches for enhanced ...

View full details
$339.95 - $339.95
$339.95
$339.95 - $339.95
$339.95
Tailored Sportsman Icefil Long Sleeve- Almost Pale Blue - Vision Saddlery

Tailored Sportsman Icefil Long Sleeve- Almost Pale Blue

$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

*These products are price controlled by the supplier/ distributor. The Tailored Sportsman Ice Fil Shirt is the stylish way to keep your cool t...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Tailored Sportsman Icefil Long Sleeve- BLUEST BLUE - Vision Saddlery

Tailored Sportsman Icefil Long Sleeve- BLUEST BLUE

$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95

*These products are price controlled by the supplier/ distributor. The Tailored Sportsman Ice Fil Shirt is the stylish way to keep your cool t...

View full details
$109.95 - $109.95
$109.95
$109.95 - $109.95
$109.95
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - BluHeaven/Tan - Vision Saddlery

Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - BluHeaven/Tan

$279.00 - $279.00
$279.00
$295.00
$295.00 - $295.00
$295.00

The Mid Rise is 1″ higher in the rise than its Low Rise counterpart. The Tailored Sportsman name is synonymous with quality and classic style. The ...

View full details
$279.00 - $279.00
$279.00
$295.00
$295.00 - $295.00
$295.00
Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Periwinkle/Tan - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Hyacinth/Tan - Vision Saddlery

Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Hyacinth/Tan

$295.00 - $295.00
$295.00
$295.00 - $295.00
$295.00

  *These products are price controlled by the manufacturer The Mid Rise is 1″ higher in the rise than its Low Rise counterpart. The Tailored Sports...

View full details
$295.00 - $295.00
$295.00
$295.00 - $295.00
$295.00
Tailored Sportsman Quilted Belt - French Blue - Vision Saddlery
Tailored Sportsman Quilted Belt - French Blue - Vision Saddlery
Sale Sale

CLEARANCE Tailored Sportsman Quilted Belt - French Blue

$174.95
$174.95 - $174.95
$174.95
$129.95
$129.95 - $129.95
$129.95

*These products are price controlled by the manufacturer These beautiful belts are hand made in Italy by the Tailored Sportsman. They are two inche...

View full details
$174.95
$174.95 - $174.95
$174.95
$129.95
$129.95 - $129.95
$129.95
Sale Sale
Tailored Sportsman Tech Light Trophy Hunter Jodhpurs - Vision Saddlery

Tailored Sportsman Tech Light Trophy Hunter Jodhpurs

$299.95 - $299.95
$299.95
$299.95 - $299.95
$299.95

The Tailored Sportsman Hunter Jodhpurs the most classic Jodhpur. They feature a low rise waist and 4-way stretch in Tailored Sportsman's new techni...

View full details
$299.95 - $299.95
$299.95
$299.95 - $299.95
$299.95
Tailored Sportsman Ladies Tech Light Mid Rise Silicone Knee Breech - TAN - Vision Saddlery
Tailored Sportsman Ladies Tech Light Mid Rise Silicone Knee Breech - TAN - Vision Saddlery

Tailored Sportsman Ladies Tech Light Mid Rise Silicone Knee Breech - TAN

$339.95 - $339.95
$339.95
$339.95 - $339.95
$339.95

The Tailored Sportsman Ladies Tech Light Mid Rise Silicone Knee Breech combines advanced Tech Light fabric with silicone knee patches for enhanced ...

View full details
$339.95 - $339.95
$339.95
$339.95 - $339.95
$339.95
Tailored Sportsman Childrens Front Zip Boot Sock Breech - Periwinkle & Tan - Vision Saddlery
Tailored Sportsman Childrens Front Zip Boot Sock Breech - Periwinkle & Tan - Vision Saddlery

Tailored Sportsman Childrens Front Zip Boot Sock Breech - Periwinkle & Tan

$269.00 - $269.00
$269.00
$269.00 - $269.00
$269.00

*These products are price controlled by the manufacturer The Tailored Sportsman girls breeches are the gold standard for young rider's show attire ...

View full details
$269.00 - $269.00
$269.00
$269.00 - $269.00
$269.00
Tailored Sportsman Childrens Front Zip Boot Sock Breech - Rosewood & Tan - Vision Saddlery
Tailored Sportsman Childrens Front Zip Boot Sock Breech - Rosewood & Tan - Vision Saddlery

*CLEARANCE* Tailored Sportsman Children's Front Zip Boot Sock Breech - Rosewood & Tan

$249.00 - $249.00
$249.00
$249.00 - $249.00
$249.00

*These products are price controlled by the manufacturer The Tailored Sportsman girls breeches are the gold standard for young rider's show attire ...

View full details
$249.00 - $249.00
$249.00
$249.00 - $249.00
$249.00
Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Vicuna/Black - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Vicuna/Black - Vision Saddlery

*CLEARANCE* Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Vicuna/Black

$269.00 - $269.00
$269.00
$269.00 - $269.00
$269.00

*These products are price controlled by the manufacturer The Mid Rise is 1″ higher in the rise than its Low Rise counterpart. The Tailored Sportsma...

View full details
$269.00 - $269.00
$269.00
$269.00 - $269.00
$269.00
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - Violet & Tan - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - Violet & Tan - Vision Saddlery

Tailored Sportsman Mid Rise Trophy Hunter Front Zip Boot Sock Breech - Violet & Tan

$279.00 - $279.00
$279.00
$295.00
$295.00 - $295.00
$295.00

  The Mid Rise is 1″ higher in the rise than its Low Rise counterpart. The Tailored Sportsman name is synonymous with quality and classic style. Th...

View full details
$279.00 - $279.00
$279.00
$295.00
$295.00 - $295.00
$295.00
CLEARANCE - (20/R)Navy Tailored Sportsman Low Rise Trophy Hunter Front Zip Breeches - Vision Saddlery
CLEARANCE - (20/R)Navy Tailored Sportsman Low Rise Trophy Hunter Front Zip Breeches - Vision Saddlery
Sale Sale

CLEARANCE - (20/R)Navy Tailored Sportsman Low Rise Trophy Hunter Front Zip Breeches

$279.00
$279.00 - $279.00
$279.00
$182.95
$182.95 - $182.95
$182.95

FINAL SALE. *These products are price controlled by the supplier/ distributor. Feel and look your best while riding! One of the most popular styles...

View full details
$279.00
$279.00 - $279.00
$279.00
$182.95
$182.95 - $182.95
$182.95
Sale Sale