Men’s Capsule Wardrobe: How to Choose Your Underwear (Guide)

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New year, new wardrobe! Men’s capsule wardrobes are trendy right now, yet I didn’t even know the term existed until last month. I love the concept: keep your wardrobe to a curated collection of shirts, pants, shoes, shorts, etc., such that you can mix and match to always look stylish without thinking. Of course, I pioneered this concept for years as I wear only a few shirts and a few shorts and pants, all in various shades of blue. The only reason why I didn’t get famous is that capsule wardrobes are also supposed to be stylish. 

Capsule wardrobes save time for men in the morning when getting ready and save money and shopping trips. If you buy a select number of high-quality clothing pieces and have a timeless design, you can wear this wardrobe for years – perhaps decades – without needing new clothing. High-quality clothes don’t succumb to wear and tear easily, and timeless looks never go out of style.

I believe guys need to plan their underwear drawer as much as any part of their capsule wardrobe. Yet blog articles about designing a men’s capsule wardrobe overlook an essential component: underwear. What’s the point of looking sharp if your underwear is uncomfortable? Or having to replace your underwear every few months because you buy cheap multi-packs without any thought?

If you are taking the time to plan out your wardrobe, take time to plan out your underwear collection (as well as how to fold your underwear). Below I go through how to choose underwear for a men’s capsule wardrobe. Then I present my ideal underwear collection for a capsule wardrobe for 21 days. But please note that this is only one way to design your underwear collection out of infinite choices; only you know your underwear preferences the best. 

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Underwear Considerations for a Men’s Capsule Wardrobe

Before selecting your capsule underwear, take a few minutes to understand your underwear needs. A little planning now will ensure you have a capsule underwear collection that is timeless, stylish, and comfortable.

• Chafing: Chafing is a skin irritation caused by loose or baggy clothes. If your upper legs get scratched from your shorts or trousers, stick to longer-leg styles such as boxer briefs or long-leg boxer briefs. Guys who don’t chafe can explore shorter styles such as trunks and briefs.
• Work Climate: In what kind of climate do you spend most of the day? Men who work outdoors primarily will have different needs than men sitting at an office desk all day, primarily due to sweat and chafing. Guys working outdoors, especially in hot climates, will want moisture-wicking underwear, while men at a desk will cherish soft, form-fitting styles.
• Business and Business Casual: If you wear dress pants regularly, you’ll need to purchase higher-quality underwear that doesn’t have thick leg bands (if you wear boxer briefs or trunks). Why? Boxer brief lines! The male version of the visible panty line is alive and well. I can’t tell you how many times I know what style of underwear a guy is wearing just by looking at his legs while walking. While I find visible boxer brief lines hot, many guys would be horrified if they knew. I’ll pick out styles that minimize this.

• Fly or No-Fly: Having a functional fly on your underwear is a personal preference and does not affect your capsule underwear collection. However, if you strongly prefer having a fly, buy underwear with a fly. Requiring a functional fly will limit your selection, so you may want to buy a test pair of no-fly underwear to see if you can make it work. I don’t usually use my underwear fly for almost a decade, and I don’t miss it.
• Leisure Activities: You’ll want to ensure you have enough underwear for leisure activities, especially if they differ from your working job. For example, if you work at an office but hit the gym and go hiking on the weekends, you’ll want to stock up on quick-drying underwear. Likewise, if you work outside but love to Netflix and chill on the weekends, you’ll love buying some soft modal and bamboo underwear.
• Budget: Finally, how much do you want to spend on your new underwear drawer? I find the sweet spot for men’s underwear is around the $15 per pair range. Buying 21 pairs will total up to around $325 plus tax. Can you afford this? If you can and perhaps can afford more, then not a bad idea to grab some or all undies in the $25-$35/pair range. If not, I’ll go through some ways to reduce the bill, especially down to around $10/pair.

Six Steps to Choosing Underwear for a Men’s Capsule Wardrobe

Below are my six steps to creating your capsule underwear collection. While I guide you below, use your own experience to help you. What fabric and styles do you like already? What do you not like? Take my guidance and adjust it to your personal preferences for the ultimate underwear collection for you.

Step 1: Buy Underwear for Your Work

For work, I recommend buying 15 pairs, one for each workday for three weeks. Even though work can be a serious place, I always recommend expressing yourself through the colors and patterns of your underwear as much as you want. You’ll have a lot more fun and confidence at work, plus no one will see.

Yet, I recommend two tips for work: I don’t recommend white underwear in high-sweat situations, and if you wear tight suit pants or trousers, stick with briefs or trunks.

• If you primarily work inside an office or at home, you’ll want to purchase light and soft underwear composed of modal or bamboo fabric. If you don’t want a fancy pouch and just want your standard vertical fly pouch, then get David Archy’s bamboo boxer briefs or their bamboo briefs (especially if you are upgrading from your standard Hanes or Fruit of the Loom cotton boxer briefs). They are less than $10/pair, and if you use my code hello200, you’ll get Free Shipping!
• Another fantastic inexpensive option is Jockey modal boxer briefs. They are slightly more expensive than David Archy, but you can buy them from Amazon, especially if you are a Prime member and get free shipping.

• If working outdoors is your primary occupation, you’ll want quick-drying, moisture-wicking underwear. While modal and bamboo are better than cotton in this regard, polyester and nylon-based underwear perform the best. I recommend Puma’s performance boxer briefs (read my review), and if you tend to chafe, buy 9″ longer-leg boxer briefs from Jockey.

• Wear business suits and pants to work? I’d recommend buying briefs and square-cut trunks to prevent a baggy look and boxer brief lines under suit trousers. If you’d prefer a bit more coverage than David Archy’s hip-cut briefs I recommended above, try T-Bo’s bamboo trunks instead. If you don’t wear suit pants on a regular basis, skip to step #5.

Step 2: Buy Underwear for the Weekends

For weekends, I suggest buying six pairs, one for each weekend day for three weeks): If you purchased darker, minimalist colors for your workdays, go bolder on your weekends. Weekends are your time to let loose and be playful.

• For Netflix and Chill weekends, go for modal and bamboo fabric. I’ll reiterate David Archy’s bamboo boxer briefs or T-Bo’s bamboo trunks as my picks. Alternatively, if you prefer spending weekends only wearing underwear, buy soft bamboo boxer shorts to lounge around instead. Weekends are really a time to let loose!
• Weekend warriors will want to go for polyester and nylon underwear to help stay dry and cool. Try Mack Weldon’s AIRKNITx trunks and boxer briefs, which I wear and love. For guys needing chafing protection, go with Separatec’s 8″ long-leg boxer briefs with bold colors.

Step 3: Buy Underwear for Date Nights

Finally, you’ll want to buy special underwear for date nights. Your date or significant other deserves your best underwear, regardless of whether you have been married for years or are still dating. Buy three extra pairs of sexy undies to have on hand. Men need to have sexy underwear for sexy occasions.

• Every guy needs to have a pair of plain black hip-cut briefs or trunks for a sophisticated date night. I recommend a three-pack of either T-Bo’s black bamboo briefs or Calvin Klein’s microfiber trunks (I’ve worn Calvin Klein’s microfiber trunks and boxer briefs for many years). Both brands’ black underwear is sexy and elegant, exactly what you need.

Last update on 2025-05-16 at 10:37 / Affiliate links / Images from Amazon Product Advertising API

• And here is a twist many guys won’t see coming: add a jockstrap to your collection for sexually charged nights. You can read my story here about my first jockstrap and my jockstrap revved-up sex that night. Since then, I received a second jockstrap from Teamm8, which I love. Obviously also has a wide selection of colors for a more traditional, yet playful, jockstrap.

Other Considerations for Your Underwear Collection

Now you have your underwear collection set to complete your men’s capsule wardrobe. Yet, before purchasing, here are a couple more considerations before your click Buy Now.

Avoiding Duplication

At this point, review your underwear choices. If you only have underwear of one kind – either all modal/bamboo or all polyester/nylon/mesh – then buy three extra pairs of the other kind. Purchasing a different type of underwear ensures that you have the ideal underwear for various situations.

Prefer a Functional Fly?

If you want a functional fly, note that many of the underwear I chose do not have a fly. Not having a fly is a big trend in men’s underwear, so you’ll want to be careful what you buy if this is a must have. I list some substitutes below that have a fly.

• Office/home workers and Netflix and Chill weekends: No need to substitute Separatec or David Archy underwear above as it already contains a functional fly.
• Outdoor workers and weekend warriors: It is tough to find good moisture-wicking boxer briefs with a functional fly. You’ll have to increase the budget and go for Under Armour’s Original 6″ BoxerJock or the 9″ long-leg version. I have a pair of UA’s 6″ BoxerJock, and I love it! The material is awesome, the vertical fly is easy to use, and they look sexy!

Last update on 2025-05-16 at 10:37 / Affiliate links / Images from Amazon Product Advertising API

Budget

I chose underwear above to average $15 per pair, even a bit less. This price range is the sweet spot in men’s underwear, providing great styles and fabrics for a reasonable price. However, if you can afford a higher budget, you can splurge for premium underwear providing premium design and quality.

• Home/office workers and Netflix and Chill weekends: In lieu of Separatec or David Archy, upgrade to Saxx Ultra briefs, trunks, and boxer briefs. Both of these brands feature separated penis pouches – to separate your balls from your groin – amazing quality, and a plethora of designs for both the office and playful weekends. I personally own Saxx Ultra boxer briefs, and I love them. Caution: If you are worried about boxer brief lines or bunching, Saxx designed its Ultra underwear to be a tad loose fitting. Either buy Ultra briefs or choose Saxx’s Vibe boxer briefs instead.
• Weekend warriors and outdoor workers: Likewise, go with Saxx’s Quest boxer briefs or Mack Weldon’s AIRKNITx Boxer Briefs. Both companies are high-quality and the moisture-wicking fabric is perfect for high-sweat situations.
• Sizes up to 4XL: Not all of the brands on here carry sizes up to 4XL. Yet, no need to sacrifice on comfort, quality, or design just because brands don’t cater to guys in this size range. Gruff + Tumble underwear caters to men wearing sizes large to 4XL. For indoor workers and relaxing weekends, choose their Statesman Boxer Briefs, made from modal fabric that is just as plush as bamboo underwear. For outdoor workers and sports and gym sessions, go with Gruff + Tumble’s Sportsman Compression Shorts.

• Shorts with Built-in Underwear: For the ultimate minimalist capsule wardrobe, why not combine your underwear and your shorts into one package? More and more brands are selling shorts with built-in underwear (the “liner”), which will really streamline your wardrobe. Read my pros and cons of going this route to see how these shorts can work for you.

Now Put your Underwear Plan in Action

You’ll have 24-27 pairs on your wishlist for your three-week men’s capsule wardrobe underwear collection. To summarize:

• 15 pairs for work underwear, generally in modest, neutral colors and patterns
• Six pairs for weekend underwear, generally in brighter, vivid colors and patterns
• +3 additional pairs of the opposite category if the first 21 pairs are all the same
• +3 extra pairs for special date nights

That’s it! With this underwear collection, you’ll always have underwear on stock for the right occasion, yet without needing to think or find the best pair of underwear each day. It covers the lifestyle of many guys, with adjustments allowed to fit your lifestyle the best. Once you have done this, let me know how you have enjoyed your men’s capsule wardrobe in the comments. And if you need help, don’t forget to email me at hello@mensunderwearguide.com!

P.S. Also remember to buy an underwear organizer to easily keep track of your new underwear collection!

Last update on 2025-05-16 at 10:37 / Affiliate links / Images from Amazon Product Advertising API

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