Popular Preppy Clothing for Women & Men

Everyone likes to stand out in a crowd, but there's wisdom in large numbers. These are the most popular preppy products on our site, and by extension, on the planet!

Sawyer Stretch 6 Pocket Pant by Johnnie-OSawyer Stretch 6 Pocket Pant by Johnnie-O

Sawyer Stretch 6 Pocket Pant by Johnnie-O

$ 145
Whiskey Row Leather Tab Belt in Navy by Country Club PrepCountry Club Prep 32 (fits size 30 pants) / Navy

Whiskey Row Leather Tab Belt in Navy by Country Club Prep

13 reviews
$ 59.50
Caddyshack Leather Tab Belt in Navy by Country Club PrepCountry Club Prep 32 (fits size 30 pants) / Navy

Caddyshack Leather Tab Belt in Navy by Country Club Prep

2 reviews
$ 59.50
University of Virginia Custom Lawn Belt in Light Blue by Smathers & BransonCountry Club Prep 32 (fits size 30 pants) / Blue

University of Virginia Custom Lawn Belt in Light Blue by Smathers & Branson

7 reviews
$ 175
Crafty Beer Leather Tab Belt in Green by Country Club PrepCountry Club Prep 32 (fits size 30 pants) / Green

Crafty Beer Leather Tab Belt in Green by Country Club Prep

3 reviews
$ 59.50
Country Club Prep Madras Plaid Needlepoint Belt by Smathers & BransonCountry Club Prep 30 (fits size 28 pants)

Country Club Prep Madras Plaid Needlepoint Belt by Smathers & Branson

1 review
$ 175
University of Virginia Needlepoint Belt by Smathers & BransonCountry Club Prep Navy / 30 (fits size 28 pants)

University of Virginia Needlepoint Belt by Smathers & Branson

$ 175
Rotunda Needlepoint Belt in Dark Navy by Smathers & BransonCountry Club Prep 32 (fits size 30 pants) / Navy

Rotunda Needlepoint Belt in Dark Navy by Smathers & Branson

1 review
$ 175
Smathers and Branson University of Virginia 2019 NCAA Basketball Champions Needlepoint Belt by Smathers & BransonCountry Club Prep Navy / 30 (fits size 28 pants)

University of Virginia 2019 NCAA Basketball Champions Needlepoint Belt by Smathers & Branson

3 reviews
$ 175
Country Club Prep Navy / 32 (fits size 30 pants)

The Patriotic Ribbon Belt in Navy by Over Under Clothing

8 reviews
$ 55
Country Club Prep 30 / Royal Blue

Mini Gingham Shorts in Royal Blue by Country Club Prep

1 review
$ 120
Linen Pants in Stone by Country Club Prep

Linen Pants in Stone by Country Club Prep

$ 145
Skipjack Classic Fit Pant in Sandstone Khaki by Southern TideCountry Club Prep 30W x 32L

Skipjack Classic Fit Pant in Sandstone Khaki by Southern Tide

2 reviews
$ 125
Country Club Prep Plain Front Shorts in Faded Red by Country Club PrepCountry Club Prep 28 / Faded Red

Plain Front Island Short in Faded Red by Country Club Prep

6 reviews
$ 99.50
Vineyard Vines Stretch Breaker Pants in Khaki by Vineyard VinesCountry Club Prep 30W / 30L / Khaki

Stretch Breaker Pants in Khaki by Vineyard Vines

$ 98.50
The Palm Beach Pink Linen Pant by Country Club Prep

The Palm Beach Pink Linen Pant by Country Club Prep

1 review
$ 120
Intercoastal Performance Pant in Sandstone Khaki by Southern TideCountry Club Prep 30W / 30L / Sandstone Khaki

Intercoastal Performance Pant in Sandstone Khaki by Southern Tide

1 review
$ 125
9 Inch Stretch Breaker Shorts in Jake Blue by Vineyard VinesCountry Club Prep 30 / Jake Blue

9 Inch Stretch Breaker Shorts in Jake Blue by Vineyard Vines

1 review
$ 75
Vineyard Vines 8 Inch Performance Breaker Shorts by Vineyard VinesCountry Club Prep Stone / 28

8 Inch Performance Breaker Shorts by Vineyard Vines

1 review
$ 85
Skipjack Classic Fit Pant in Stone by Southern TideCountry Club Prep 30W x 32L

Skipjack Classic Fit Pant in Stone by Southern Tide

1 review
$ 125
Flags of Our Fathers Leather Tab Belt in Light Blue by Country Club PrepCountry Club Prep 32 (fits size 30 pants) / Light Blue

Flags of Our Fathers Leather Tab Belt in Light Blue by Country Club Prep

2 reviews
$ 59.50
Country Club Prep 32 (fits size 30 pants) / Khaki

Embroidered Skipjack Belt in Sandstone Khaki by Southern Tide

$ 75
Wyatt Prep-Formance Shorts in Stone by Johnnie-OCountry Club Prep 30 / Stone

Wyatt Prep-Formance Shorts in Stone by Johnnie-O

$ 89
9 Inch Stretch Breaker Shorts in Khaki by Vineyard VinesCountry Club Prep 30 / Khaki

9 Inch Stretch Breaker Shorts in Khaki by Vineyard Vines

1 review
$ 75
The North Face Men's Class V Board Shorts by The North FaceCountry Club Prep Crystal Teal Joshua Tree Print / 30

Men's Class V Board Shorts by The North Face

$ 60
The Social Palm Linen Short in Navy by Country Club PrepThe Social Palm Linen Short in Navy by Country Club Prep

The Social Palm Linen Short in Navy by Country Club Prep

$ 95
The Broad Street Linen Short by Country Club PrepThe Broad Street Linen Short by Country Club Prep

The Broad Street Linen Short by Country Club Prep

$ 95
The Sea Breeze Linen Short by Country Club PrepThe Sea Breeze Linen Short by Country Club Prep

The Sea Breeze Linen Short by Country Club Prep

$ 95
Country Club Prep 32 / Grey

The Captain Shorts in Grey by Country Club Prep

$ 85
Vineyard Vines Stretch Breaker Pants in Lobster Reef by Vineyard VinesCountry Club Prep 30W / 30L / Lobster Reef

Stretch Breaker Pants in Lobster Reef by Vineyard Vines

$ 98.50
Vineyard Vines Canvas 5 Pocket Slim Pants by Vineyard VinesCountry Club Prep Stone / 30W / 30L

Canvas 5 Pocket Slim Pants by Vineyard Vines

1 review
$ 98.50
Plain Front Pants in Faded Red by Country Club PrepCountry Club Prep 28 X UNF / Faded Red

Plain Front Pants in Faded Red by Country Club Prep

2 reviews
$ 79.50 $ 135
The Regatta 6" Short Flat Front in Audubon Tan by Southern MarshCountry Club Prep 30 / Tan

The Regatta 6" Short Flat Front in Audubon Tan by Southern Marsh

1 review
$ 59
Country Club Prep Tan / 32Tan Seersucker Pants by Country Club Prep

Tan Seersucker Pants by Country Club Prep

$ 135
MO Columbia Leather Tab Belt in Black Ribbon with White Canvas Backing by State TraditionsCountry Club Prep Black / 30 (fits size 28 pants)

MO Columbia Leather Tab Belt in Black Ribbon with White Canvas Backing by State Traditions

$ 55
The Skipjack Classic Fit Pant in True Navy by Southern TideCountry Club Prep 32W x 30L / Navy

The Skipjack Classic Fit Pant in True Navy by Southern Tide

$ 125
The 9" Skipjack Short in True Navy by Southern TideCountry Club Prep 32 / Navy

The 9" Skipjack Short in True Navy by Southern Tide

2 reviews
$ 85
Hayes Jean Short by Southern Tide - FINAL SALECountry Club Prep White / 24

Hayes Jean Short by Southern Tide

$ 78
Country Club Prep 32 / Stone

Linen Shorts in Stone by Country Club Prep

$ 89.50
Intercoastal Performance Pant by Southern TideCountry Club Prep 30W / 30L / Stone

Intercoastal Performance Pant by Southern Tide

$ 125
Country Club Prep 32 (fits size 30 pants) / Blue

Embroidered Skipjack Belt in Yacht Blue by Southern Tide

2 reviews
$ 75