One orthodox Jewish site writes this:
There is a biblical commandment to promote segregation, which prohibits men from wearing any female garments and forbids women from wearing any clothing designated and designed for men. In biblical times women didn't wear pants (Deuteronomy 22:5). Therefore pants are considered clothing designed for men, and women are not to wear it. There is another reason why women don't wear pants. According to Jewish law it is immodest for a woman that her legs be seen.
A basic statement of the standard is: "Women are not permitted to wear pants. Women wear skirts or dresses that fall past the knee." On another, we read about the wife of a rabbi:
Sarah Gitler, the wife of Rabbi Marc Gitler of Edos, is the mother of two, a rebbetzin and an attorney who works at a Denver law firm. For Gitler, the hardest part of tzniut’s dress requirements is finding the proper attire in Denver shops.
“They don’t sell that kind of clothing in the stores,” she says. “I have to go to more stores than most people to get a single outfit.
“Like the sleeve length. If I’m looking for a dress, the sleeves have to reach my elbows. The collars can’t be too low. It’s difficult to find all that in one place.
“I’ve never found much online that’s really fashionable,” she adds. “It’s hard to find clothes that don’t look dorky and dumb. That’s really the biggest challenge. And that’s why I hate shopping.”
In the work place, Gitler wears long-sleeve blouses, black skirts, cardigans over shells and jackets.
The liberality of apparel some people choose for the work place “can be shocking,” she says. “Sometimes I see people wearing things that are so revealing that it objectifies them.
“It must be hard to carry on a conversation without noticing that.”
Gitler wears her sheitel at work but chooses hats that cover her hair for the synagogue and on Shabbat.
Like Heyman, she has noticed clothes that while meeting the literal requirements of tzniut “are really tight. Clothing covers the collarbone or the knees, but it’s so skin tight that a loose-fitting pair of pants might seem more modest. That wouldn’t be my choice when it comes to expressing modesty.”
But Gitler never wears pants.
“Friday is jeans day at work. Obviously I can’t do that.”
Tzniut also guides her behavior.
“I like to talk to people and joke with them, but I feel uncomfortable about certain subjects. I refrain from boisterousness or drawing attention to myself. I stay away from water-cooler conversations.
“People curse all the time,” she says. “Normal banter involves curse words. But I watch my language and never use those words because it’s inappropriate.”
Even if religion never came up at the office, Gitler has a feeling that her colleagues realize she is Jewish.
“To the outside world, dress is what distinguishes us.”
They call it tzniut (here you can read another expression of an orthodox Jewish women's experience). You can watch a video with an explanation by a Jewish teacher (start at about 3:30 on the pants issue). You also read it here (and here and here).
Orthodox Jews would be the ones who would take the Old Testament most literally and their belief and practice of Deuteronomy 22:5 matches up with how Christians historically followed Deuteronomy 22:5. When I say "most literally," I am understanding that they aren't practicing the sacrificial system or the priesthood, but here we get the interpretation of the Hebrew people that care about the Hebrew.
When I read the issues of orthodox Jews, I read what I can see are the concerns in obeying these passages. It doesn't fit in with the world. It feels uncomfortable. It is more a matter of worldliness than it is a matter of some new study that has opened up a more enlightened view of Deuteronomy 22:5. This is how Christians practiced for centuries, until most recently. And it just happens to coincide with everything in the culture sliding toward Gomorrah.
For more information on this topic, read the study here.
Also consider this study on the Messiah for those who revere the God of Israel.