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Price comparison

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Last updated at 12/05/2026 21:21:40

Please note: price history and price alerts are not available for some stores, including Amazon.com.au.
https://www.google.com/s2/favicons?domain=stepone.life&sz=64Step One

$29.00

Men's Boxer Brief Fly | Ahoy Sailor | Anti-Chafe Underwear for Men | Best Men's Underwear | Bamboo Viscose Compression Shorts | Easy Access | No

Free delivery between 15–26 May

Price history

Price history

Please note: price history and price alerts are not available for some stores, including Amazon.com.au.

Reviews

14 December 2023G S.

originally posted on step-one-uk.myshopify.com

Fantastic love them to quote Flanders from the Simpsons “it’s like I’m wearing nothing at all nothing at all nothing at all” however this is not true as you are supported where you need to be. Best underwear I have ever had.

18 October 2022Mathew L.

originally posted on step-one-uk.myshopify.com

A bit tight even though I chose right for my waste. Materials feel quite thin so not sure how long lasting they will be.Delivery was a bit slow.Silky smooth and feels nice against the skin.

21 December 2023Michael J.

originally posted on step-one-uk.myshopify.com

Step One's product is tops, and what is so impressive is their customer care and support!! The product is excellent. I love it, but I have to say their customer care and support are even better!! Absolutely top class on all fronts! We had a shipment go astray, and I emailed step one on the matter, got an amicable and positive response, and all was sorted in a couple of days!!! I’m a business owner, so I know the potholes that happen now and again, but these people are genuine to deal with and have their customer's care xx at the top of their list!! Regards, Michael Galway, Ireland.

Price comparison

Updated 6 months ago
Please note: price history and price alerts are not available for some stores, including Amazon.com.au.
https://www.google.com/s2/favicons?domain=stepone.life&sz=64
Step One

$29.00

Men's Boxer Brief Fly | Ahoy Sailor | Anti-Chafe Underwear for Men | Best Men's Underwear | Bamboo Viscose Compression Shorts | Easy Access | No

Free delivery between 15–26 May

Price history

Price history

Please note: price history and price alerts are not available for some stores, including Amazon.com.au.

Reviews

14 December 2023

Fantastic love them to quote Flanders from the Simpsons “it’s like I’m wearing nothing at all nothing at all nothing at all” however this is not true as you are supported where you need to be. Best underwear I have ever had.

G S. originally posted on step-one-uk.myshopify.com
18 October 2022

A bit tight even though I chose right for my waste. Materials feel quite thin so not sure how long lasting they will be.Delivery was a bit slow.Silky smooth and feels nice against the skin.

Mathew L. originally posted on step-one-uk.myshopify.com
21 December 2023

Step One's product is tops, and what is so impressive is their customer care and support!! The product is excellent. I love it, but I have to say their customer care and support are even better!! Absolutely top class on all fronts! We had a shipment go astray, and I emailed step one on the matter, got an amicable and positive response, and all was sorted in a couple of days!!! I’m a business owner, so I know the potholes that happen now and again, but these people are genuine to deal with and have their customer's care xx at the top of their list!! Regards, Michael Galway, Ireland.

Michael J. originally posted on step-one-uk.myshopify.com
19 November 2023

Love them that’s why I bought more, they were recommended some time back. Only thing is I have not got to get rid of my old style underwear as they do not compete with these step one.

Michael W. originally posted on step-one-uk.myshopify.com
26 June 2024

Best undies on the planet! This is my third order from Step One in seven plus years. Each time I grab a bunch. I have not had chaffing once since switching to these and they last! Worth every penny.

Nadim originally posted on stepone.life
2 December 2022

Well enough made but vastly over priced and for me at least they dont live up to the hype. That said I bought a pair for each day of the week; more as a give it go thing I guess.Not great if you have a bit of a belly on you; the waisband folds itself over. only undies I've ever had that do this.

Neil B. originally posted on step-one-uk.myshopify.com
11 November 2023

Step One Underwear is the most comfortable Underwear I have come across! I particularly like the soft fabric; the immaculate stitching; the leg length & most of all the fantastic Pouch!In 2018 I had a life-saving operation, the result was I lost 50% of my left Testical, so the cleverly designed Pouch in Step Ones are worth their weight in Gold to me!Another side effect of wearing Step Ones, that I hadn’t realised when writing my last review, is that when you have an accident of the No.2 variety ( yes, it still happens to me occasionally, (I’m 24 year post Head-injury & now Disabled), because of how well fitting they are, Step One Underwear act as a close-fitting Nappy; allowing for much easier tidying up from what otherwise, would have been a lengthy job.Well ... MoreStep One Underwear is the most comfortable Underwear I have come across! I particularly like the soft fabric; the immaculate stitching; the leg length & most of all the fantastic Pouch!In 2018 I had a life-saving operation, the result was I lost 50% of my left Testical, so the cleverly designed Pouch in Step Ones are worth their weight in Gold to me!Another side effect of wearing Step Ones, that I hadn’t realised when writing my last review, is that when you have an accident of the No.2 variety ( yes, it still happens to me occasionally, (I’m 24 year post Head-injury & now Disabled), because of how well fitting they are, Step One Underwear act as a close-fitting Nappy; allowing for much easier tidying up from what otherwise, would have been a lengthy job.Well done Step One.

Richard M. originally posted on step-one-uk.myshopify.com
13 November 2023

Fast becoming my favourite brand of underwear. I have worn Justwears, Jockeys, Isobaa, SuperNatural and these are the best.They’re comfortable, don’t ride up and great designs/patterns. Hopefully these last longer than 18 months and they’ll be my favourites, as I’m fed up of pairs not lasting long and wearing out.

customer originally posted on step-one-uk.myshopify.com
Best pants I've ever owned
22 September 2024

Must buy a few more. These are the most comfortable pants I've ever worn. Great product. thanks

Stamper originally posted on johnlewis.com

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Step One Men's Boxer Brief Fly Anti-Chafe Underwear for Men Ahoy Sailor M
Step One Men's Boxer Brief Fly Anti-Chafe Underwear for Men Ahoy Sailor M$33.00
From Step One
Boxer Brief Fly - Ahoy Sailor
Boxer Brief Fly - Ahoy Sailor
Boxer Brief Fly - Ahoy Sailor
Boxer Brief Fly - Ahoy Sailor
Boxer Brief Fly - Ahoy Sailor
Boxer Brief Fly - Ahoy Sailor
Boxer Brief Fly - Ahoy Sailor
Boxer Brief Fly - Ahoy Sailor

Boxer Brief Fly - Ahoy Sailor

(575 reviews)

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.

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.

$29.00 - $33.00

in 2 offers

last seen 12 May 2026

The lowest price we last saw for Boxer Brief Fly - Ahoy Sailor was $29.00 at Step One (last seen 12 May 2026). Prices may have changed since.

The all-time low we recorded was $29.00 on 28 Aug 2025.

Prices last updated 12 May 2026.

Boxer Brief Fly - Ahoy Sailor

$29.00

last seen 12 May 2026
(575 reviews)

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.

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.

Size:

3XL
4XL

Color:

Ahoy Sailor