Why do so many Messianic/Hebrew Roots women dress like frumps and peasants? The Bible tells us to dress modestly; nowhere does it say we have to look like throwbacks to the 1800s.
I believe a lot of this is is spawned by insecure men who feel the need to dominate women because, every once in awhile you'll see some man telling women they cannot wear pants, and that they cannot cut their hair, and that women must keep their hair covered. And, of course, they attempt to use Scripture to support their opinions on women's apparel.
But is that really true? Let's see what Scripture actually says:
1 Peter 3: 1. So also you wives, be subject to your husbands; that by your pleasing behavior you may gain over without difficulty those who are disobedient to the Word, 2. when they see that you conduct yourselves with reverence and chastity. 3. And don't adorn yourselves with the external ornaments of curls of the hair, or of golden trinkets or of costly garments. 4. But adorn yourselves in the hidden person of the heart with a mild and pure spirit, an ornament that is precious before Elohim. 5. For so also the Set Apart women of old who trusted in Elohim, adorned themselves and were subject to their husbands....
1 Timothy 2: 9. So also, that women (appear) in a chaste fashion of dress; and that their adorning be with modesty and chastity; not with curls or with gold, or with pearls, or with splendid robes; 10. but with good works as is becoming to women who profess reverence for Elohim.
Titus 2: 1. But as for you, the things that belong to wholesome doctrine. 2. And teach the older men to be watchful in their minds and to be sober, and to be pure, and to be sound in the faith, and in love and in patience. 3. And so also the elder women that they be in behavior as is becoming to the Fear of Elohim; and not to be slanderers; and not to be addicted to much wine; and to be teachers  of beautiful things, 4. making the younger women to be modest, to love their husbands and their children, 5. to be chaste and Set Apart and to take good care of their households and to be obedient to their husbands, so that no one may reproach the Word of Elohim.
In 1 Timothy, Rav Shaul commands that women keep silent in the assembly and not assume authority over a man. However, here in Titus 3:2, the older women are instructed to lead by examples of their own piety and to teach the younger women in the Fear of Elohim. (The word malpan most certainly means to teach.) Y'shua is frequently called a Malpana almost as often as he is called a "Rabbi."
So, the concern in 1 Timothy (according to a footnote in the Aramaic English New Testament) seems not so much about women speaking, but to not speak out of turn while the official leader is teaching. Surely, such action is disrespectful universally; neither is it normal for men to be given such liberty. Rav Shaul encourages the older and spiritually mature women to both teach and be examples for the younger women, as they are able to help safeguard young men and women from "worldly lusts." We don't see endorsement of women congregational leaders in Paul's writings, but we certainly do see encouragement for women to exercise leadership in modesty and be Set Apart unto YHWH.
Matthew 6: 31. Therefore, do not be anxious or say, What will we eat? Or what will we drink? Or what will we wear? 32. For all these things, the peoples those of the world require these things, and your Father who is in heaven also knows that you require all these things. 33. But first seek the Kingdom of Elohim and His righteousness and all these things will be added to you. 34. Therefore, be not anxious about tomorrow for tomorrow is anxious for itself. Sufficient for the day is its evil.
Bottom line: Dress modestly and behave in a holy, godly manner! Scriptures suggest that
women not flaunt their beauty by wearing revealing clothing and
adornments designed to attract others in a sexual way. That is ALL. There's nothing that says women cannot wear pants or that they must keep their hair covered at all times (hair is to be covered when they are praying or prophesying - 1 Cor. 11:3-15)!
Pants are a relatively modern invention and if you want to get technical, then MEN should be wearing dresses too, because, back in Biblical times, both men and women wore loose robe-like clothing
and tunics. NOBODY wore pants! Pants aren't just a "man" thing; there are pants made for men and pants made for women, so don't let anyone tell you, you HAVE to wear dresses down to the ankles and all the way up to your ears! Just dress MODESTLY! You know what that means....