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Over Under Clothing

Progression of Freedom Belt by Over Under Clothing

2 reviews
Regular Price
$ 28.95
Sale Price
$ 28.95
Regular Price
$ 55.00
Sold Out
Unit Price
This item is Final Sale.

Color: Blue

Size: 32 (fits size 30 pants)

What's better than one American flag? Multiple American flags. Extra points when they are featured on a preppy belt made specifically for the most fashionable of American men. With this belt, you'll feel like you are wearing a piece of American history, as it features the evolution of the American flag throughout the decades of our great country. Perfect for the 4th of July when paired with khaki shorts, boat shoes, a navy blue polo, and an ice cold brew in hand.

Over Under certainly did not skip on the quality with this Progression of Freedom Belt. Starting with a thick woven cotton backing, a smooth embroidered overlay, and finishing with genuine leather tabs and a solid brass buckle, this belt is an all around luxury. Grab one today for yourself or the fellow preppy American men in your life!

  • Classic cotton canvas backing
  • Made in the ole US of A 
  • Solid brass hardware 
  • Genuine leather tabs
  • Please order one size up when purchasing your belt. For example: if you are a 34" waist you will wear a 36".


  • Features multiple different American flags from history
  • You'll be the preppiest man in the room when wearing this belt with a pair of khakis and a white polo 
  • Sturdy woven backing won't slip

Shipping Options

All orders ship for free via USPS First Class Shipping (4-5 day delivery). Orders $195+ ship for free via USPS Priority Shipping (2-3 day delivery). UPS Next Day Air shipping is available for $35, but is not available on Fridays or Saturdays.

Returns Policy
View the full return policy in this link. Final Sale items are not eligible for return, exchange, or store credit. All items must be unworn, unwashed, and in the original condition. All returned items must meet the Return Deadlines listed below. Items received by our Return Department that do not meet the criteria listed on the Return Slip will not accepted or processed. Customers are responsible for return shipping. Country Club Prep will pay once to ship an exchanged item back to customer.

Return Deadlines
Refunds: Items must be received within 45 days of the original order date. Refunds will be applied to the original form of payment only. Please allow 2 weeks after your return is processed for the refund to show in your bank account. Shipping fees are not refundable. If original form of payment is unavailable, a CCP Store Credit will be issued.

Exchanges: Items must be received within 60 days of the original order date. All exchanges must be of equal or lesser value. CCP Store Credit: Items much be received within 90 days of the original order date.


Let’s lay out the facts. You’re here either because you’re preppy, you know someone who’s preppy, or you heard how incredibly handsome, sophisticated, and witty we are. As a betting institution, CCP has its money on the first option (and/or the third).

You’re in the right place. Country Club Prep’s mission in business and in life is to find the best preppy designers out there and to bring them to you under one metaphorical roof. Think of us as Zappos for preppy clothing.

When you’re looking for something preppy - ANYTHING PREPPY - visit CCP first. It’s our job to carry that item, but if we don’t, guess what - we’ll tell you where to find it. Your complete satisfaction is just that important to us.

If you’ve browsed the website, then you already know - there’s a veritable cornucopia of reasons to buy your preppy products from CCP. Incredible selection from incredible designers? Check. Unrivaled membership rewards? Double check. Outstanding customer service and an overriding desire to give you the best possible shopping experience? Triple check (so many preppy pink and green checks...).

We’re adding new designers and products to CCP every day. Literally. If there’s a designer that you love that we don’t currently carry, let us know. Send us an email at customerservice [at] countryclubprep [dot] com. If it’s a good fit, we’ll make it happen.

For that matter, feel free to contact us for any reason (not involving manual labor). We’re happy to help, and we’re always eager to show you why preppy has a home.

Country Club Prep
Est. 2012

Customer Reviews
5.0 Based on 2 Reviews
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Elaine R.
United States United States

Spectacular Quality

This is the 3rd belt I purchase from Country Club Prep, and I have to say the quality is amazing. The 1st belt I purchased was last Christmas for my son, who wears it everyday to school. It still looks great and I have even washed it a few times. The 2nd belt I purchased was for my husband and he absolutely loved it. This Christmas I purchased the 3rd belt, also for my son because he will not wear any other belt that is not from here. The belt is true to size, it looks very elegant and comfortable. I love the way they look on both of them. Will definitely make future purchases. I wish you had smaller sizes for kids because my younger son wants one just like his big brother's.

United States United States


Great experience. The belt is fantastic and quite unique. There are a number of belts out there featuring the star and stripes, but not many that include historical examples. The belt ran true to size (order 2-3” larger than your trouser waist size). I loved the tag “Not Made in China” fixed to the belt when I received it.