Men’s Valentine’s Day Underwear: What to Buy? (Shopping Guide)

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Table of Contents

• Shinesty’s X-Rated Collection
• Jockstraps as Men’s Valentine’s Day Underwear
• The Elegant Black Trunk (or Brief!)
• Couple’s Matching Undies
• Final Word on Men’s Valentine’s Day Underwear

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I feel somewhat dirty creating a men’s Valentine’s Day underwear list. Not dirty in the Valentine’s Day way, like oooh dirty, tell me more. I mean dirty like lowest common denominator clickbait dirty. My goal is to be helpful, not just gather clicks. Plus, I have a particular phobia of most print underwear.

Yet, after pondering this more dilemma for somewhere around 178 seconds, I decided to make a Valentine’s Day page. Why? So guys – and their partners – don’t buy random novelty underwear that will never get worn again. I want you to buy nice, comfortable, high-quality men’s Valentine’s Day underwear. Underwear to have fun on Valentine’s Day and have fun for the rest of the year.

Instead of purchasing boxer shorts with big hearts on them and calling it a day, buy some of the men’s Valentine’s Day underwear below and be proud of your purchase!

Shinesty’s X-Rated Collection

I featured Shinesty in my Guide to Pouch Underwear as Shinesty includes a separated single-pouch in all of its men’s underwear. I recommend that all guys try out pouch underwear as it makes a difference. And what better gift for Valentine’s Day than underwear that helps out a guy’s balls?

As I noted, many companies now offer underwear with ball pouches, so why Shinesty for Valentine’s Day? I highlight Shinesty because of their X-Rated Underwear Collection. Even though I’m not too fond of novelty print underwear, I love how humourous the X-Rated prints are. The theme is perfect for a fun Valentine’s Day.

I own a pair of Shinesty’s Big Bang X-Rated Boxer Briefs, which combines my love of astronomy, humour, and sex. You can read my full review here, but while I loved Shinesty’s soft modal fabric, I wasn’t a fan of their U-shaped pouch. I prefer I-shaped or V-shaped pouches instead. But having said that, Shinesty’s boxer briefs were still quite comfortable, and I love wearing them, especially because of the pattern and the soft modal fabric.

• Length/Style: Shinesty offers standard 6″ boxer briefs and 8.5″ long-leg boxer briefs as well as briefs and 3″ trunks! Most of the X-Rated designs come in different lengths, so both brief lovers and go-to boxer brief wearers will enjoy wearing Shinesty. Click here to see all of the X-Rated designs, and then click on a pattern to see the options for different cuts.
• Price: $$$$. Expect to pay $28+ for each pair, although if you subscribe to Shinesty’s monthly underwear subscription, the price drops to $18/pair. Also, see below on multipack pricing to save up to 33%.

• Material and Fabric: Speaking of love, Shinesty’s makes most of its underwear using my favorite material, modal (95% modal/5% elastane, which is a common modal underwear blend). If you haven’t heard of or tried modal underwear, you must try it out!
• Fly: Shinesty offers underwear with and without functional vertical flys. Make sure you select the correct option when purchasing!
• Branded Waistbands: I prefer subdued logos on my underwear waistbands, so Shinesty’s simple logo is fantastic for me.
• Multipacks: Yes, you can use Shinesty’s Multipack builder to save up to 33%. The discounts start at 5% for ordering two pairs, and go up to 33% for ordering 8+ pairs. You can build-a-pack by clicking here.
• Design Country: United States

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Jockstraps for Men’s Valentine’s Day Underwear

I purchased my first jockstrap in 2022. Then I got my second jockstrap in 2023. While I am not into wearing it as day-to-day underwear, it served one part of my life very well: sex. That is why I recommend adding jockstraps to your men’s Valentine’s Day underwear cart!

Jockstraps are spicy and show off the male body very well. They provide sensual exposure of the butt while leaving the most private part of a man’s body left to desire. Forget about only using it on Valentine’s Day! Jockstraps are fantastic year-round for date nights and sexy time.

Yet, like the purposes of this article, you can’t just purchase any jockstrap off the shelf and toss it afterward. If jockstraps are new to you and your partner, read my review about my first time and take the time to select a jockstrap that works best for you and your partner.

• Length/Style: Jockstraps don’t come in different lengths, so the main differentiator is the waistband thickness. Thick waistbands (first image below) provide an old-school appearance to jockstraps, similar to old-fashioned “athletic supporters” in school. Most jockstraps, however, use similar waistbands to other men’s underwear for a modern low-rise appearance (second image below).

Last update on 2025-05-14 at 10:27 / Affiliate links / Images from Amazon Product Advertising API

Last update on 2025-05-14 at 10:27 / Affiliate links / Images from Amazon Product Advertising API

• Price: Varies; however, you’ll find the sweet spot in the +/- $15-20 per pair range. Brand names, modal/bamboo/microfiber blends, and well-designed jockstraps cost more than the cheapest jocks out there and are worth the extra money.
• Material and Fabric: Select a jockstrap with the same fabric as you already prefer. I love modal and bamboo, yet I made a mistake by purchasing a cotton jockstrap. Stick to what you like!
• Fly: Jockstraps don’t have flys as there is no room. Sorry!
• Design: Although I mentioned the different waistband designs above, you’ll need to consider the color and pattern of the pouch as well. I love patterns and darker colors, although you’ll want to consider bolder colors and patterns for men’s Valentine’s Day underwear.
• Branded Waistbands: Like the examples above showing how waistband thickness alters the look of a jockstrap, so does a brand’s logo. As jockstraps already push the sexual envelope, I prefer to balance that with a subdued yet sophisticated pattern and waistband.
• Multipacks: Multipacks are definitely possible, depending on the brand. The examples from Amazon above are multipacks.

If you like the look of jockstraps but aren’t comfortable with having your butt exposed, try tanga briefs instead.

The Elegant Black Trunk (or Brief)

In my opinion, the sexiest underwear for men is simple yet elegant black trunks. Black always looks terrific on guys, and the simplicity of the solid color shows off well. A guy wearing black trunks – or briefs! – exudes understated confidence that compounds the sex appeal. Plus, since all guys can use a pair of black trunks or briefs throughout the year, this is also a convenient gift.

To be clear, I am not referring to a pair of Hanes cotton black boxer briefs with a gray waistband. Buying a pair of black trunks as men’s Valentine’s Day underwear must satisfy two main criteria: a black waistband and a great feel. A black waistband creates a seamless look and draws attention to the male pelvis having a different colored waistband can’t do as easily. Combined with a material such as modal, bamboo, or microfiber that is soft to the touch, you and your partner will enjoy underwear foreplay while increasing sexual desire.

David Archy black trunks are elegant for Valentine’s Day but are also amazing for year-round wear – two gifts in one! I am a massive fan of modal, so these 92% modal/8% elastane trunks are soft to rub your hands over in bed, and soft enough to wear at work or on the weekends. These specific black trunks feature David Archy’s Dual-Pouch system. I own several pairs of sister brand Separatec’s Dual-Pouch briefs and boxer briefs, and you can read my review of their briefs and boxer briefs (they use the same pouch).

David Archy Black Trunks with Dual Pouch

For briefs, consider buying Tommy John’s Second Skin briefs in all black. I own a pair of Second Skin boxer briefs and the fabric is amazing. They are super comfortable and for guys who love flys, the Horizontal Fly is easy to use (a lot of horizontal flys are cut too small).

Luxurious Tommy John Second Skin briefs.

Couples’ Matching Valentine’s Day Underwear from MeUndies

My husband and I don’t share matching underwear, although we do share underwear (a benefit of being gay – a much larger underwear collection!). However, some couples find it sexy to wear matching underwear. If so, then Valentine’s Day is a great time to show it off.

For gay guys and women who wear men’s underwear, you don’t need anything special – just buy two pairs of whatever underwear you want. However, for men and women who wear men’s and women’s underwear respectively, it can be a bit of a challenge.

MeUndies has a great selection of matching men’s and women’s underwear. For men, you can choose from briefs, trunks, boxer briefs, and boxer shorts. Women have a much larger selection, from briefs to boyshorts to thongs.

MeUndies also has an extensive selection of colors and patterns, so it is easy to get designs that both of you like. There are three Valentine’s Day-themed pairs available, but no need to get Valentine’s Day-themed pair. Plus, if you find wearing matching underwear sexy, you can save 26% by opting for a monthly subscription from Me Undies.

Final Word on Men’s Valentine’s Day Underwear

Valentine’s Day is the best day of the year to buy new men’s underwear, yet is underrated for this purpose. Worse, many retailers treat it as a kitsch holiday for selling underwear, flogging tacky and cheap boxers with giant hearts. No! Treat Valentine’s Day as the day of love and purchase classy men’s underwear for your partner and yourself.

Furthermore, I selected underwear above that isn’t just for Valentine’s Day and won’t see the light of day again. What better gift than underwear that is used throughout the year? Practical gifts are far more caring than gag gifts (most of the time) and I hope you treat Valentine’s Day seriously to purchase men’s underwear that provides comfort and sex appeal. Men deserve nothing less.

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