Tommy John Quick Draw Fly

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Founded in 2008, Tommy John went from being a little-known underwear startup to a premier destination for high-quality undergarments.
The brand offers underwear — and many other essentials — in a variety of fits, sizes, and materials so that people of all needs and budgets can experience modern comfort.
Insider Reviews likes Tommy John underwear so much, we named it the best overall pick in our men's underwear guide. Personally, it's the only underwear brand that I've spent my money on over the last few years.
To potentially save at Tommy John, visit Insider Coupons for the latest deals and promotions.

Most people don't shop for underwear with the same level of thought and consideration as they would for a mattress or a pair of shoes, but I'm here to tell you that your choice in underwear is just as, if not more, important. After all, we wear it for hours on end daily and even nightly.

As someone who is constantly trying out new pairs to review and keep our best men's underwear guide up-to-date, I've tested dozens of different underwear brands, and I have a favorite: Tommy John.

Making underwear better than it has been is the very root of Tommy John. The company was founded in 2008 and it has since grown into many people's go-to brand for underwear and other wardrobe essentials.

Tommy John stands out from other brands because it has invested an extremely generous amount of time and effort into designing undergarments for modern use. Everything from the fit to the shape to the materials has been taken into consideration.

Tommy John underwear styles

Most men, including myself, prefer boxer briefs over boxers or briefs, but Tommy John has a fit for everyone's needs:

Boxer Brief — 8-inch inseam
Relaxed Fit Boxers — 6.5-inch inseam
Mid-Length Boxer Brief — 6-inch inseam
Trunk — 4.5-inch inseam
Square Cut — 3-inch inseam
Brief — No inseam
Leggings — 18.5-25.5-inch inseams

Since I prefer boxer briefs over other underwear styles regardless of the brand, my experience with Tommy John underwear is almost exclusively based on those. I've also tried the trunks and didn't like them as much, but that's just me personally. You can use my review and your own preferences to help decide which styles will work best.

What they're like to wear

The very first time I put on a pair of Tommy John Boxer Briefs, I couldn't help but notice they were substantially longer than other boxers. It was a bit weird visually and it took a few minutes to get used to having material that far down my leg, but I came to appreciate the length almost immediately.

We've all had to do that awkward underwear adjustment through our jeans or the brazen reach up our shorts to pull down our underwear legs, but with Tommy John, I haven't had to do that. Ever. Along with the great fit, the added length helps keep things in place so you're not uncomfortable throughout the day.

I also appreciate the design of the Quick Draw horizontal fly because it's easy to access, but still secure. You won't have any accidental slip-outs.

I've never had any complaints about support with Tommy John, but the brand recently released Hammock Pouch underwear that keeps everything where it needs to be. I like the extra support they provide, but I'm also still very happy with the other pairs I own.

Tommy John materials

Tommy John has a pretty wide selection of material types, and I've tried a good amount of them, but I will say that I don't think any one is exponentially better than the other. Tommy John's fit and construction are what make the brand so good — the material is what makes the underwear a better fit for your specific usage.

The core materials are Second Skin, Cool Cotton, Air Mesh, 360 Sport, and Basic Cotton. Here's a quick rundown of what you can expect from each material:

Second Skin — Luxurious, soft, and silky feeling. This is the closest thing to not wearing any undies.
Cool Cotton — Breathable, moisture-wicking, and keeps you cooler than traditional fabric. Great for avoiding uncomfortable underwear soaked in sweat.
Air Mesh — Super lightweight, breathable, and quick-drying. Great for daily use or traveling light.
360 Sport — Stretchy, durable, and moisture-wicking for your workouts. You'll also find a built-in storage compartment for keys or a phone.
Go Anywhere — Four-way performance stretch material that's moisture-wicking, anti-odor, and anti-microbial. Great for daily use.
Cotton Basics — Soft, lightweight cotton with a comfortable amount of stretch. Great for daily use on a budget.

Tommy John also has Second Skin x Air underwear that offers the luxurious feel of the former, while providing the breathability of the latter in high-heat areas.

Cons to consider

Originally, the only thing that might be considered a negative was the price, but the brand has done a great job at introducing different materials at more accessible price points. While the most expensive pair of Boxer Briefs at Tommy John is $42, which is admittedly a lot for a single pair of underwear, Tommy John also has a Cotton Basics 2-Pack for $19.50.

Although you can still buy a 6-pack for less from other brands, Tommy John is a great value considering the level of quality the brand delivers — even in the basic styles.

Bottom Line

As a Reviews writer, I'm in a unique position where I don't often have to pay for underwear. I have many more pairs than the average person.

But even so, Tommy John is literally the only underwear brand that I've spent my own money on over the last few years. And trust me, I don't just like spending money to spend it; they're really that good.

If you struggle with uncomfortable underwear — waistbands digging into your skin, legs that don't keep their shape, lack of support in your nether regions — Tommy John is a great solution.

Even if you don't struggle with discomfort (you might just be so accustomed to wearing bad underwear that you've grown used to those shortfalls), I still recommend giving Tommy John a try. You don't have to toss out your entire underwear drawer, but after one pair of Tommy Johns, I bet you'll be ready to add more.

Shop Tommy John underwear now.

Amir Ismael

Senior Reporter, Insider Reviews

Amir Ismael is a senior reporter for Insider Reviews, Insider's e-commerce branch of the service journalism team. As a collector of sneakers and fashion, Amir is passionate about all things related to style. He's covered everything including the industry's shift to producing more sustainable clothing, the most comfortable loungewear, all of the best places to shop for affordable business casual attire, and more. He's used his expertise in footwear and the footwear industry to review all kinds of shoes from sportswear giants, well-known casual brands, and startups. Amir's coverage also includes eyewear, watches, and grooming products like electric razors and men's skincare. Since the beginning of the coronavirus pandemic, Amir has led Insider Reviews' face masks coverage with thoughtful recommendations based on CDC guidelines, expert opinions, and his own testing. During his time at Insider, Amir previously handled deals of the day coverage, and worked as a generalist writing hundreds of reviews ranging from phone cases and headphones to bed sheets and blenders, and has also covered major shopping holidays including Amazon Prime Day, Black Friday, and Cyber Monday. Before joining the Insider Reviews team in 2017, worked as a freelance writer for Complex Sneakers and Sole Collector where he contributed to daily sneaker news and release dates, feature-length articles, and interviews with artists, designers, and athletes. Amir graduated from William Paterson University in 2015 with a degree in journalism and public relations. Say hello to Amir at aismael@insider.com or on Instagram @amirjismael. Learn more about how our team of experts tests and reviews products at Insider here. Learn more about how we test style and beauty products.