I have made some research and this is what i got (and sorry about my grammar )
So it called
Panchira (パンチラ) refers to a brief glimpse of a woman's underwear.
Panchira (パンチラ) refers to a brief glimpse of a woman's underwear. The
term carries risqué connotations similar to the word 'upskirt' in
English usage. The word is a portmanteau of "panty" (パンティー pantī) and
chira, the Japanese sound symbolism representing a glance or
glimpse. It differs from the more general term "upskirt" in that
panchira specifies the presence of underpants (the absence of which
would more accurately be described as ノーパン; nōpan).
Traditionally, Japanese women did not wear underwear. On December 16,
1932, there was a fire in the Tokyo Shirokiya department store. Legend
has it that some of the female staff tried to use their kimonos to
cover their privates as they climbed down ropes from the higher
floors, and accidentally fell to their deaths. Japanese newspapers
began agitating for women to start wearing 'drawers' (ズローズ zurōzu),
but seemingly had little impact at the time. In a 1934 survey by a
Fukuoka newspaper, 90% of the women surveyed were still not wearing
'drawers' a year and a half after the fire.2
As noted below, the development of panchira in Japanese popular
culture has been analyzed by a number of American and Japanese
writers. Many observers link the phenomenon to the Westernization of
Japan following World War II.7 During the occupation, fashions,
ideas, and media previously unavailable were accessed by the local
population, leading to a slight relaxing of earlier taboos.
Western-style clothing (including women's underwear) gained popularity
in the post-war period, reinforced through numerous media outlets —
magazines, newspapers, films, journals, and comics.
At least one Japanese source traces the beginnings of panchira to the
release of The Seven Year Itch in 1955. The media coverage
surrounding Marilyn Monroe's iconic scene fueled the emerging Japanese
craze. According to architectural historian Shoichi Inoue, the
practice of "scoring" a glimpse up young women's skirts became
extremely popular around this period; "Magazines of the time have
articles telling the best places where panties could be viewed".
Inoue also writes that actress Mitsuyo Asaka spurred the popularity of
the word 'chirarizumu' (チラリズム 'the thrill of catching a brief glimpse
of a women's nether regions') by parting her kimono to show off her
legs in her stage shows in the late 1950s.
In 1969, the Japanese oil company Maruzen Sekiyū released a television
commercial featuring Rosa Ogawa in a short mini-skirt that gets blown
up by the wind with her forming her lips into an 'O' in surprise. This
led to children imitating her line "Oh! Mōretsu" (Oh！モーレツ, too much,
radical), and a fad for sukāto-mekuri (スカート捲り flipping up of a girl's
skirt). Ogawa subsequently appeared in a TV show Oh Sore Miyo (Oh!
それ見よ, literally "look at that," but actually a pun on 'O Sole Mio,' a
neapolitan song 'my sunshine') that again featured scenes of her
mini-skirt blowing up.
For anime/manga culture, it's 'partially' answered from this question.
Where did the anime trope of Clothing Damage / Clothes being torn originate?
it was from this manga, Shameless School
Harenchi Gakuen (ハレンチ学園, lit. "Shameless School") is a Japanese media
franchise created by Go Nagai. Harenchi Gakuen was one of the manga
serialized in the very first issue of Shueisha's manga magazine Weekly
Shōnen Jump. The series was the first big success for Go Nagai. It is
also considered as the first modern erotic manga, sometimes considered
the first hentai manga, though Nagai never used explicit sexual
situations in the original run of the manga.
And from the same wiki, it was written
By the late 1960s, panchira had
spread to the mainstream comic industry, as fledgling manga artists
such as Go Nagai began exploring sexual imagery in boys' comics
(shōnen manga). Adult manga magazines had existed since 1956 (e.g.
Weekly Manga Times), but it is significant to note the introduction of
sexual imagery into boys manga. Millegan argues that the ecchi genre
of the 1970s rose to fill a void left by the decline of Osaka's
lending library network:
and i read an article about Shueisha’s Weekly Shonen Jump came under fire for running a busty spread on Yuragi-sō no Yūna-san (Yūna of Yuragi Manor). The illustration sparked conversations about ecchi works in a magazine that is largely seen as reading material for kids under 14 years of age.
From what i could tell, the originate of "skirt-flipping" is from short mini-skirt that gets blown up by the wind ). There is a book with titles,
Perversion and Modern Japan: Psychoanalysis, Literature, Culture that explain about this topic, but i couldn't copy the reference's, since its licensed. You could read the book online Here