Skip to content
Tailor & Barber Tailor & Barber

A men's lifestyle blog focusing on style, fashion, and grooming.

  • Home
  • Shop the Feed
  • Style Thoughts
    • Suits
    • Sport Coats
    • Trousers
    • Shirts
    • Shoes
    • Outerwear
    • Knitwear
  • Shave and Groom
    • Fragrance
    • Shaving
    • Hair
  • Required Reading
  • Contact
Tailor & Barber
Tailor & Barber

A men's lifestyle blog focusing on style, fashion, and grooming.

Men's Underwear She Actually Wants You to Wear

Men’s Underwear She Actually Wants You to Wear

Posted on February 13, 2018February 12, 2018 By Drew

I spent the better part of last week asking my female blogger friends what type of men’s underwear they like. Yep, it was uncomfortable as it sounds. But I figured with Valentine’s Day fast approaching (this Wednesday!) that it might not be a bad idea to get some answers. I know that, for me, my confidence in the bedroom is directly linked to my partner’s attraction to me. I know that’s probably not the healthiest mental self-image and borderline codependent, but that’s just how my brain works. So, I want to look as good as I can, and certainly not present myself as unappealing when the romance starts.

I discovered two important pieces of information this past week during my research. First, women actually think much less about your underwear than you probably think about theirs. Almost everyone I asked had to think before they answered. I would be willing to bet that if someone asked you what your favorite type of women’s underwear is, you could answer much quicker. I consider this good news for me. Stop putting so much thought into it. Second, almost every woman also had the same answer once they gave it some thought: boxer-briefs. One, however, did say boxers. When pressed a little more to make a distinction between longer boxer-briefs and shorter trunks, the split was about 50-50.

My Favorite Men’s Underwear

So what should you wear? First of all, skip the briefs. Not one woman said her preferred men’s underwear were “tighty-whities”, and I concur. I just don’t think they’re as flattering as some other types. Now, as to the remaining three (trunks, boxer-briefs, boxers), my personal opinion is that it depends on your body composition.  As you probably know, I’m a big proponent of dressing for your body, not the not style of the moment. If you’re really fit and have a flat stomach, I think trunks are the way to go. Like skipping a belt on a custom suit, trunks minimize the break in the line of your body and show off those gains. For the average guy, a pair of longer boxer-briefs definitely fit the bill. They’re comfortable, flattering, and a quality pair won’t bunch up on you. If you’re carrying some extra weight, boxers re the way to go. Like a double-breasted suit, the extra fabric will compliment your build, and the free-flowing fabric allows for some breathability minimizing excess sweat.

Look, I know discussing this isn’t something guys usually talk about with each other. (You should try doing it with women sometime!) However, all women will tell you that confidence is key, and that doesn’t change whether your clothes are on or off. Feeling your best about how I look, is the kind of boost I could use on Valentine’s Day.

Share this:

  • Share on Threads (Opens in new window) Threads
  • Share on X (Opens in new window) X
  • Share on Facebook (Opens in new window) Facebook
  • Share on Pinterest (Opens in new window) Pinterest
  • Share on Tumblr (Opens in new window) Tumblr
  • Share on Reddit (Opens in new window) Reddit

Like this:

Like Loading...
Style Thoughts Underwear Brooks BrothersCalvin KleinDerek RoseHugo BossMack WeldonRoyal HighniesSunspelZimmerli

Post navigation

Previous post
Next post

Related Posts

Knitwear Spier & Mackay Sweater Review

Spier & Mackay Sweater Review

Posted on January 13, 2020January 12, 2020

I think sweaters are the ultimate pairing of comfort and style. I don’t need to wear a restrictive button-up shirt underneath if I don’t want to. Even when I do, I leave the top button unbuttoned. I can even escape the choking neck tie if I want to. Of course,…

Share this:

  • Share on Threads (Opens in new window) Threads
  • Share on X (Opens in new window) X
  • Share on Facebook (Opens in new window) Facebook
  • Share on Pinterest (Opens in new window) Pinterest
  • Share on Tumblr (Opens in new window) Tumblr
  • Share on Reddit (Opens in new window) Reddit

Like this:

Like Loading...
Read More
Outerwear In Favor of the Double-Breasted Trench Coat 1

In Favor of the Double-Breasted Trench Coat

Posted on February 5, 2020February 4, 2020

Last week Kenneth Starr showed up at the Trump impeachment trial wearing a khaki double-breasted trench coat (and an ill-advised cowboy hat). While I agree that a fedora would have been a much better choice of headwear, I have to take issue with the number of comments I saw online…

Share this:

  • Share on Threads (Opens in new window) Threads
  • Share on X (Opens in new window) X
  • Share on Facebook (Opens in new window) Facebook
  • Share on Pinterest (Opens in new window) Pinterest
  • Share on Tumblr (Opens in new window) Tumblr
  • Share on Reddit (Opens in new window) Reddit

Like this:

Like Loading...
Read More
Shoes Beckett Simonon Yates Oxford Brogues

Beckett Simonon Yates Oxford Brogues

Posted on February 25, 2019February 24, 2019

Last time I took a look at a pair of Beckett Simonon shoes, I wrote about their Dean Oxfords, which are relatively formal shoes with a plain cap toe. The clean lines of a cap toe pair very well with the simple, clean look of a business suit. Mine were…

Share this:

  • Share on Threads (Opens in new window) Threads
  • Share on X (Opens in new window) X
  • Share on Facebook (Opens in new window) Facebook
  • Share on Pinterest (Opens in new window) Pinterest
  • Share on Tumblr (Opens in new window) Tumblr
  • Share on Reddit (Opens in new window) Reddit

Like this:

Like Loading...
Read More

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

  • Instagram
  • TikTok
  • Threads
  • YouTube
  • Pinterest
  • X
  • Facebook

Subscribe

Recent Posts

  • What I Wore April 9, 2026
  • What I Wore April 6, 2026
  • What I Wore April 4, 2026
  • What I Wore March 25, 2026
  • My Favorite Shoes at Each Price Point
©2026 Tailor & Barber | WordPress Theme by SuperbThemes
%d