Boxer Brief Fly

Cheeky Cheddars

Sale price$28.50



Sizing Chart



THICKER Legs? Then go for the BOXER BRIEFS
THIN Legs? Then TRUNKS are for you

Our 30-Day First Pair Guarantee means you can try 1 pair for up to 30 days and if it's the wrong size, then we'll send out a different size, for FREE. Yeah.. Free 💪
Note: If the replacement pair is still not a good fit, we can no longer process a refund or send another replacement pair. I'm sure you'd understand! 
2XS / (Size 4/8) 21-22in
XS / (Size 8/12) 23-26in
Small 27-30in
Medium 31-32in
Large 33-35in
Extra Large 36-40in
2XL 41-45in
3XL  46-49in
4XL 50-52in
5XL 53-56in
6XL 57-59in

Add 3 more and save $6

Pairs3 5 10
Price per pair$26.50$23.50$20.50
Excludes Sale Items

Are you tired of constantly adjusting your underwear throughout the day? Introducing our ultra-comfortable men's Boxer Brief + Fly, a gate for your mate, specifically designed for guys with thicker legs.

Our First Pair Guarantee ensures that you'll love them or they're FREE. The 3D Comfort Pouch features a hidden elastic band that surrounds you perfectly, providing all-day support and comfort. Our UltraGlyde™ ride-up resistant panels ensure that your underwear stays in place, no matter what activities you're engaging in.

Made from a super soft bamboo viscose blend, these underwear not only feel amazing on your skin, but they're also environmentally friendly. The bamboo viscose material wicks away moisture, keeping you feeling fresh and dry all day long. Plus, our bamboo viscose is produced in a closed-loop system, making it a sustainable choice.

With 95% viscose made from bamboo and 5% spandex, these underwear offer the perfect balance of stretch and support. Mix and match sizes, colours, and styles to create your perfect multi-pack. Don't miss out on the ultimate comfort and support of our men's bamboo viscose underwear.

FREE shipping is available for all orders in the United States! Rates and estimated delivery times are below:

United States

  • FREE for all orders!

Western States

  • Metro 1-3 business days from dispatch
  • Rural 2-4 business days from dispatch

Eastern States

  • Metro 2-4 business days from dispatch
  • Rural 3-6 business days from dispatch


  • $9.95 for all orders
  • 5-10 business days from dispatch

We’ve partnered up with USPS, UPS and Fedex to provide an unparalleled experience, and ensure you get your product on time.


Our team of stealthily trained Ninja's will endeavor to dispatch your order from our warehouse ASAP. You will receive a notification when the package leaves our warehouse and is then placed in the lovely hands of our shipping partners! This is us highlighting that we don't deliver your shiny fresh amazing Step One ourselves, it's typically providers, which are out of our control.

If we hear of any delays through our providers we will do our utmost best to advise you as soon as we become aware of any delay.

Please also note that during major events such as Black Friday or Mid Year sale, these shipping times can be longer. 

Thank you for being a legend and buying a pair of life changing, super-soft, anti-chafe, reduced ride-up, minimal adjustment, organically grown and FSC certified, 55,000 5-star reviews .... Step Ones. You'll love em. Promise.

We are so confident you'll love your Step Ones, we'll give you a FULL REFUND on your FIRST PAIR if you don't like them for whatever reason.


There’s a hidden piece of elastic around the pouch to surround you and your boys perfectly, keeping everything neatly in place!


These friction resistant panels come with anti-chafe technology, so they prevents leg ride up and stop those awkward moments of re-adjusting in public!


This organic material, produced in a close-loop system, wicks away sweat and moisture and allows you to breathe all day long!