Remember that commercial with Michael Jordon? I'm sure that wasn't the first time the boxer vs brief question was asked, but it did make the question popular.
Me, I'm a rebel. I prefer boxer briefs on my hubby. You get the best of both worlds. They're tight enough to be sexy -- because I hate that baggy boxer look -- and yet, they don't make me think of panties -- as briefs do -- when I look at them.
And because my hubby has really sexy legs and I like the way they look in boxer briefs . . . but I digress.
The first men's underwear was probably the
Loincloth, a simple strip of material or leather. A loincloth was also used to describe material pulled between the legs and fastened like a diaper. Not a good look for anyone :( Greek and Roman men reportedly wore loinclothes.

During the Middle Ages, loinclothes were replaced by loose trouser like pants called
Braies. Braies were a step-in design and laced at the waist and mid-calf. Wealthy men also wore
chausses.
By Renaissance, braies became shorter to accommodate longer styles of chausses -- and chausses gave way to hose. But since neither braies nor chausses were meant to be worn beneath they weren't technically underwear.
Braies were replaced by cotton, silk or linen
drawers which were worn for years and years and years. And years. I couldn't find much information on how much -- if any -- the basic design changed. However, in the mid 1800's mass production of underwear began and people started to buy their drawers instead of making them at home. The
Unionsuit also became popular in the mid 1800's -- 1868 actually -- and had the drop seat in the back.
In 1874, the
Jock Strap came along to provide support for the bicycle jockeys riding upon cobblestone streets.
The first underwear print ad ran in the Saturday Evening Post in 1911, an oil painting, not a picture. That would have been indecent! In WWI soldiers were issued button front shorts though they were often still worn with a union suit. (Which by the way became 2 pieces in 1910 - what we call
long-johns).
By 1935 Coopers Inc. sold the world's first men's briefs, the design dubbed
Jockey since it provided the support once only offered by a jock strap. 30,000 pairs of new
Jockeys sold within the first 3 months of introduction. In the 1950's manufacturers began to make men's underwear from colored and/or printed material. In the 1970's and 1980's advertisers began appealing to the sexual side of selling, foregoing the long time ad practice of comfort and durability. Speaking of comfort - or lack thereof - the
thong became popular in the 1990's.
So, what do you prefer on your man? Boxer, brief, thong . . . or commando?