Ahhh, the age old question: should I wear boxers or briefs?

The answer is simple: wear what feels most comfortable.

Naturally, that doesn’t mean throw your common sense out the window – there’s still a time and a place for everything and underwear is no exception, although you probably won’t be judged on how ‘in’ your undergarments look.

Just make sure you stick to good quality cotton in whatever style you eventually choose…

“What are my options?”

Boxers: These are, unsurprisingly, styled on the shorts that boxing aficionados wear. Loose fitting with a range of fly types (buttons, toggles, poppers) it’s not hard to see the appeal of this ‘free and easy’ undergarment.

Briefs / Y-fronts: Although traditional briefs fell from fashion during Mark Wahlberg’s Calvin Kline rein, this underwear classic has gained new followers during the past decade or so. Briefs offer good lower support and present a cleaner line down below.

Boxer Briefs: The best of both worlds; the hold of briefs with the fit of boxers. The male equivalent of the wonder bra, many guys don’t like the thought of returning to the traditional fits, minus the figure defining line of boxer-briefs.

Long Johns: A fast-fading relic; long johns are warm and toasty, but don’t do much for your love life. Generally impractical for twenty-first century living, it’s probably best you look around for alternatives unless thermal endurance is your main priority.

Rules of Engagement
So what’s the rule of thumb when it comes to wearing undies, other than the most obvious one: “make sure you’re wearing a clean pair”…

  1. Avoid the ‘banana hammock’. Your genitalia doesn’t require that much support; it’s pretty uncomfortable and unflattering for all concerned. Find underwear that fits a little less snuggly.
  2. Conceal your threads. No one wants to see what brand of underwear you’re sportin’ so shun the rap-star ‘low riding’ fit and keep your labels tucked safely away beneath your jeans.
  3. Throw out the old. Your underwear goes through a lot of ‘wear and tear’, so junk them when they start looking thin. You don’t think twice about the pair with holes until you’re suddenly ahem in a romantic situation where somebody special can take a good close look…
  4. Keep away from ‘comedic’ underwear. That slogan may seem like hilarious wordplay at the time of purchase, but the crude jokes are probably going to do more harm than good in the long run, if you know what I mean.
  5. Avoid the ‘tighty whiteys’. White Y-fronts never remain that way for long, not to mention the negative social connotations. Anyway, what’s wrong with buying a pair of briefs with a bit of color?

About The Author

Johnathan Bell is the founder, owner and main author of Guy Style Guide, a website dedicated to everyday male fashion, style and grooming. The primary mission? To guide clueless men through the tricky mindfield that is the growing world of male couture. Find him on , Twitter and Tumblr.

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