Skip to content

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 Mid Rise Trophy Front Zip Boot Sock Breech - Periwinkle/Tan - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Periwinkle/Tan - Vision Saddlery

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00
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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00
Tailored Sportsman Icefil Long Sleeve- DIRT ROAD - Vision Saddlery
Tailored Sportsman Icefil Long Sleeve- DIRT ROAD - Vision Saddlery Sale Sale

Tailored Sportsman Icefil Long Sleeve- DIRT ROAD

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

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

View full details
$109.95
$109.95 - $109.95
$109.95
$87.96
$87.96 - $87.96
$87.96
Sale Sale
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 beautiful belts are hand made in Italy by the Tailored Sportsman. They are two inches in width to perfectly fit in Tailored Sportsman trophy ...

View full details
$174.95
$174.95 - $174.95
$174.95
$129.95
$129.95 - $129.95
$129.95
Sale Sale

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00
Sale Sale

Tailored Sportsman Icefil Long Sleeve- MISTY LILAC

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

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

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 Front Zip Boot Sock Breech - Periwinkle/Tan - Vision Saddlery

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

  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
$279.00 - $279.00
$279.00
Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Periwinkle/Tan - Vision Saddlery
Tailored Sportsman Mid Rise Trophy Front Zip Boot Sock Breech - Surfer Blue/Tan - Vision Saddlery

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00
Tailored Sportsman Low Rise Velcro Bottom Breeches - Vision Saddlery
Tailored Sportsman Low Rise Velcro Bottom Breeches - Vision Saddlery
Sold out

Tailored Sportsman Low Rise Velcro Bottom Breeches

$239.00 - $239.00
$239.00
$239.00 - $239.00
$239.00

Feel and look your best while riding! One of the most popular styles from THE TAILORED SPORTSMAN™, the Trophy Hunter Low-Rise Breech is updated in...

View full details
$239.00 - $239.00
$239.00
$239.00 - $239.00
$239.00
Sold out

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00

Tailored Sportsman Quilted Belt - Designer Red

$174.95 - $174.95
$174.95
$174.95 - $174.95
$174.95

These beautiful belts are hand made in Italy by the Tailored Sportsman. They are two inches in width to perfectly fit in Tailored Sportsman trophy ...

View full details
$174.95 - $174.95
$174.95
$174.95 - $174.95
$174.95
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
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

The Tailored Sportsman girls breeches are the gold standard for young rider's show attire and this model has the comfortable elastic sock bottoms. ...

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

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

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

The Tailored Sportsman girls breeches are the gold standard for young rider's show attire and this model has the comfortable elastic sock bottoms. ...

View full details
$269.00 - $269.00
$269.00
$269.00 - $269.00
$269.00
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

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

$279.00 - $279.00
$279.00
$279.00 - $279.00
$279.00

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 - $279.00
$279.00
Tailored Sportsman Belt W 5Plates- Texture Black - Vision Saddlery
Tailored Sportsman Belt W 5Plates- Texture Black - Vision Saddlery

Tailored Sportsman Belt W 5Plates- Texture Black

$50.00 - $50.00
$50.00
$50.00 - $50.00
$50.00

FINAL SALE. Tailored Sportsman Belt in Xsmall. This belt comes equipped with 5 empty silver nameplate slots that you can customize to your heart's ...

View full details
$50.00 - $50.00
$50.00
$50.00 - $50.00
$50.00