I was Dresses Only through half of my 20s, all of my 30s, and a third of my 40s.  I wore dresses to show my femininity, and to be modest.

When I switched from reading the King James Bible, to reading the Young's Literal Translation, my eyes were opened to many things.  An actual, legitimate, literal translation of the Bible is a powerful thing, as you find out that some translations translate the same Hebrew/Greek word as various different English words, so you don't know that it was all the same word. For example, the Greek word diakonos.  

On the flip side, we may see different English words in the Bible that are speaking of something similar, and just assume they are the same Hebrew/Greek word, and that the translators were just taking literary license.  Such is the case with Deuteronomy 22:5.  That is the main Scripture used by many to claim that Christian women must wear dresses. The Young's Literal Translation of this verse is as follows:

"The habiliments of a man are not on a woman, nor doth a man put on the garment of a woman, for the abomination of Jehovah thy God [is] any one doing these."  -Deuteronomy 22:5 YLT

Notice we see that a man is not to put on the "garment" of a woman.  That is pretty clear that men are not to be transvestites or cross dressers.  They are not to cause confusion about their gender by dressing in a way that is recognized by society as that of the opposite gender.  This is usually easily understood by most who read this passage, regardless of the Bible translation they have read it from.

Now look at the instructions to the women.  It says a woman is not to have on "the habiliments of a man."  The Young's Literal Translation largely tries to stay with the same English word that literally translates from the Hebrew/Greek, so we already see a hint here, that "garments" and "habiliments" must be translated from two separate Hebrew words, and they are.

"Garments" is translated from the Hebrew word śimlâ, which literally means clothing, or garments.  This Hebrew word appears in the Bible 29 times, and refers to clothing, or a cloth that covers the body.  Here is another place where we see the same Hebrew word:

"And Pharaoh sendeth and calleth Joseph, and they cause him to run out of the pit, and he shaveth, and changeth his garments (śimlâ), and cometh in unto Pharaoh."  - Genesis 41:14 YLT

We see then that where Deuteronomy says "nor doth a man put on the garment of a woman," it means just that.  Men are not to wear women's clothing.

What of the word "habiliments," when it references that women are not to wear the habiliments of men?  Habiliments is translated from the Hebrew word kᵊlî, which does not specifically mean clothing! 
kᵊlî means an article, vessel, object, utensil, implement, apparatus, or equipment.  This Hebrew word appears in the Bible 325 times.  It means something prepared as an apparatus or implement.  The King James translators mostly translated this word as "vessel," or "instrument."  They only translated it as "that which pertaineth" once, and that's in their translation of Deuteronomy 22:5, which says:

"The woman shall not wear that which pertaineth (kᵊlî) unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the Lord thy God."  -Deuteronomy 22:5 KJV

Yet, they usually translated kᵊlî as "vessel," so they could have also translated the above as:

"The woman shall not wear a vessel (kᵊlî) [that's] unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the Lord thy God."  -Deuteronomy 22:5

Meanwhile, recall that the Young's Literal Translation (YLT) translated this word as "habiliment" in Deuteronomy 22:5.  The YLT also translates kᵊlî as "habiliment" in 1 Samuel 17:40, where it says:

"And he taketh his staff in his hand, and chooseth for him five smooth stones from the brook, and putteth them in the shepherds' habiliments that he hath, even in the scrip, and his sling [is] in his hand, and he draweth nigh unto the Philistine."  -1 Samuel 17:40 YLT

The KJV translates kᵊlî as "bag" in 1 Samuel 17:40.

In 2 Kings 11:8 the YLT translates kᵊlî as "weapons," which is fitting. The KJV does the same.

"and ye have compassed the king round about, each with his weapons (kᵊlî) in his hand, and he who is coming unto the ranges is put to death; and be ye with the king in his going out and in his coming in.'" 2 Kings 11:8 YLT

You won't find kᵊlî translated as clothing or garment in the YLT, because that's not what it means.  It is habiliment, implement, or weapon.  Habiliments are what a person wears or uses for a specific trade or purpose.  If they are a shepherd, their shepherd's bag is their habiliment.  If they are a soldier, their weapons and armor are their habiliments.

Does this mean women can't be shepherds or warriors? No!  Rachel was a shepherd:

"He is yet speaking with them, and Rachel hath come with the flock which her father hath, for she [is] shepherdess;"  -Genesis 29:9

And Jael killed a man in battle, as we read about in Judges 4.  Her habiliment/weapon was a tent stake. 

Now let's take another look at our passage in question:

"The habiliments of a man are not on a woman, nor doth a man put on the garment of a woman, for the abomination of Jehovah thy God [is] any one doing these."  -Deuteronomy 22:5 YLT

A man is not to dress in clothing that is seen as woman's clothing by others, and a woman is not to wear habiliments that were known only as habiliments that just men wore.  A modern day male habiliment would be a jock strap. That is a habiliment that never has a use for a woman to wear. Women are forbidden from donning habiliments that are only for men - such as jock straps, and men are forbidden from wearing women's clothing.

As you see, this passage doesn't say that women have to wear dresses only, and can't wear pants.  Pants are not a habiliment, as pants are not a weapon, bag, jock strap, or any other type of habiliment.  They are a garment. This passage doesn't say that women can't wear certain garments, just not certain habiliments.  The whole point in Deuteronomy 22:5 is that men should look like men, and women should look like women.  We're not supposed to blur the line between genders.  A woman should look like a woman, and a man should look like a man.

I've heard the argument that women shouldn't wear pants, because there's not one instance in the Bible of women wearing pants.  That is a flawed argument, because there is also not one place in the Bible about women wearing bras (garment), or carrying wallets (habiliment), either, but neither of these things are wrong.  Men didn't wear pants in the Bible either, so to say that women shouldn't wear pants, because women in the Bible didn't wear pants would also have to mean that men shouldn't wear pants either, because both the men and women wore robes.  Women wore robes which were recognized in society as female styled clothing, while men wore robes that were recognized in society as male styled clothing.

The only mention of 'pants' in the Bible is "trousers," or what the KJV calls "breeches."  Trousers/breeches are from the Hebrew word miḵnās, which means UNDERWEAR.  Using the law of first mention, we see this is obvious:

"And make thou for them linen trousers to cover the naked flesh: they are from the loins even unto the thighs"  -Exodus 28:42

Today, we'd call this type of clothing "boxer underwear."  

This word is only in the Bible 5 times, with the above quoted passage being the first mention.  We get more info about these "trousers" in the second mention:

"and the mitre of linen, and the beautiful bonnets of linen, and the linen trousers, of twined linen"  -Exodus 39:28

So now we see this boxer underwear is to be made out of twined linen.  

And in the third mention:

"that the priest hath put on his long robe of fine linen, and his fine linen trousers he doth put on his flesh, and hath lifted up the ashes which the fire consumeth with the burnt-offering on the altar, and hath put them near the altar"  -Leviticus 6:10

Here we see verification that the breeches or trousers are not pants, but linen boxer underwear, as we see in the above that they are to be worn under a "long robe."

And, since we looked at three of the five times these breeches or trousers (miḵnās) appears in the Bible, we might as well look at the other two times, as well:

"a holy linen coat he putteth on, and linen trousers are on his flesh, and with a linen girdle he girdeth himself, and with a linen mitre he wrappeth himself up; they [are] holy garments; and he hath bathed with water his flesh, and hath put them on."  -Leviticus 16:4

"Linen bonnets are on their head, and linen trousers are on their loins, they are not restrained with sweat."  -Ezekiel 44:18

If you read the context and surrounding verses of ALL the above five times breeches or trousers (miḵnās) - underwear - appears in the Bible, you'll see that EACH time, it is referring to what is to be worn by the Levitical priests, NOT all men.

I've heard the argument that the only time pants are mentioned in the Bible, they are only on men, and therefore only men are to wear pants.  As you've seen from the above, that argument is 100% fallacious.  We see that these "pants" are actually NOT pants, but underwear, and are to be worn under ROBES, and that this underwear is for the Levitical priests.  Using the flawed logic fallacious argument stated above, we'd then need to alter that argument to stating that it's a sin to wear underwear, unless you are a Levitical priest, and since there are no Levitical priests in the New Testament, Christians are not allowed to wear underwear. Does that make sense?  Of course not!

Therefore, we honestly and logically conclude that pants are not mentioned in the Bible, but the trousers mentioned are what we'd call boxer underwear today, and that these were commanded for the Levitical priests to wear under their robes, but it nowhere says that anyone else who'd like to wear underwear can't.  It was optional for the men and women, but mandatory for the priests.  Notice also it said "robes," as priests, all men, and all women wore robes. No one wore pants in the Bible.

In going back to our original passage one final time:

"The habiliments of a man are not on a woman, nor doth a man put on the garment of a woman, for the abomination of Jehovah thy God [is] any one doing these."  -Deuteronomy 22:5

A man is not to wear clothing that society sees as female only. This can't mean men couldn't wear "dresses" in Bible times, because both men and women wore "dresses" - robes.  They were just not to wear robes that were known as women's robes.

A woman is not to wear habiliments that society sees as habiliments for men only.  A shepherdess can carry a shepherd's habiliment bag; she'd carry one that was more feminine looking, which is probably what Rachel the shepherdess did. Jael didn't carry the weapons that society at that time deemed were only men's weapons, she killed the enemy with a tent stake.

Society determines what looks male, and what looks female.  This is getting very twisted in today's culture, as it was two times prior - right before the flood, and right before the judgement on Sodom and Gomorrah.  What do we do then?  We continue to wear what recent society deemed male or female clothing before the gender confusion delusion took front stage.  Both men and women can wear t-shirts and pants, for example, just as both men and women used to wear robes.  Women's shirts and pants are made differently than men's, and look female.  The point is to look like your gender, and not cause any confusion in that regard.

Deuteronomy 22:5 can't be saying that women are forbidden to wear pants, because:

1) NO ONE wore pants when that was written, not even the men.

2) It doesn't mention clothing the women shouldn't wear, it mentions habiliments.

We now move on to the two passages used in the New Testament that some people use, to state that Christian women have to wear dresses and skirts only, and no pants:

"In like manner also the women, in becoming apparel, with modesty and sobriety to adorn themselves, not in braided hair, or gold, or pearls, or garments of great price, but -- which becometh women professing godly piety -- through good works."  -1 Timothy 2:9-10

It doesn't say women have to wear dresses.  In fact, the only physical things it has to say about how women are to dress is "in becoming apparel," and "not in braided hair, or gold, or pearls, or garments of great price."

"Becoming" above is from the Greek word kosmios, which is an adjective, and means "becoming," or "decent."  An adjective is a word that describes a noun.  Therefore the noun it describes tells us what it it is referring to.  This Greek word is only in the Bible twice.  The only other place it appears is in the below:

"it behoveth, therefore, the overseer to be blameless, of one wife a husband, vigilant, sober, decent (kosmios), a friend of strangers, apt to teach"  -1 Timothy 3:2

In the above it is referring to decent behavior.  In our 1 Timothy 2:9-10 passage, the adjective "becoming" (same as decent) is for the noun "apparel."  Therefore we see that here the word is referring to decent (becoming) clothing.  In other words, the Christian woman is to wear the clothing that would be proper to wear by a woman professing decent behavior, which is synonymous with the end of this passage, where it says "which becometh women professing godly piety."

Interestingly, the Greek word underlying "apparel" here, is katastolē, which is a feminine noun, and this is the only time that Greek word is in the Bible.  It is two Greek words put together.  Kata - means covering, and is the base word for the woman's headcovering in 1 Corinthians 11.  Stole - means long robe.  Therefore, katastolē literally means feminine long robe, and this is fitting, because at that time, both men and women still dressed in robes.  Some of the Greek robes were togas or skirts, which could be shorter on men.  It's saying here that the women were to wear the longer robes.

How does this translate to today's society, where robes are now generally only worn over night clothes around bedtime?  Becoming apparel during the time the above passage was written was to wear a long robe.  In today's culture that is NOT becoming apparel, and would be considered inappropriate.  In other Greek literature, we see the word katastolē merely pertaining to general women's clothing, and that is how it is to be taken, now.  Becoming apparel is therefore female apparel that is becoming of a Christian woman who is "professing godly piety."  Therefore the clothing would not be expensive, nor would she worry about expensive jewelry or overdone hairstyles.  The braided hair here refers to the jewels that women used to braid in their hair to show off their standing in society, or as little temples in their hair to their false gods.

Our 1 Timothy 2 passage tells us that instead of Christian women being so focused on their outward appearance, they should be focusing on their inner person - "which becometh women professing godly piety -- through good works," and that rather they should adorn themselves with a modest and sober (not an emotional wreck) character - "with modesty and sobriety to adorn themselves."

Do you see the catch here?  Women who are all bent on trying to get Christian women to be dresses/skirts only are breaking the above!  We are told not focus on our outward appearance, but on our inner person!  Let's let Scripture interpret Scripture and see if this is indeed correct.  We now move on to our third passage in the Bible that some people try to use, to say that Christian women shouldn't wear pants...

"Whose adorning -- let it not be that which is outward, of plaiting of hair, and of putting around of things of gold, or of putting on of garments, but -- the hidden man of the heart, in the incorruptible thing of the meek and quiet spirit, which is, before God, of great price"  -1 Peter 3:3-4

For those who think the above in any way says a woman should be dresses only, then following that same path of dyslogia, the Christian woman is actually supposed to be naked at all times - "let it not be...putting on of garments."  Yet, we know that's not what this passage is saying, either.  This passage is saying the same thing as our 1 Timothy 2 passage, in that Christian women are not to be focusing on their outward appearance - "whose adorning -- let it not be that which is outward."  It then goes on to say that Christian women shouldn't be focused on their hair styles, or jewels/accessories, or their clothing - "let it not be that which is outward, of plaiting of hair, and of putting around of things of gold, or of putting on of garments."

It then goes on to say what Christian women should actually be focused on -  which is "the hidden man of the heart" - their inner person.  They are to adorn their inner person with a "meek and quiet spirit."  Meek means an attitude opposite of pride, and a quiet spirit means the woman of God isn't to be in emotional turmoil. She THINKS, and doesn't just go off of feelings and the emotions of the moment.

The word "adorning" in the above, is from the Greek word kosmos.  Kosmos means world.  It is partially where we derive our word cosmos.  This Greek word is in the Bible 187 times.  186 of those times it is translated as "world," and only once did the KJV translators and the YLT Bible translate it as "adorning."  Kosmos doesn't mean clothing, it means world.  This drives home even more how the Christian woman is being instructed in the above passage to not be focused on externals - or the worldly.

The above, translated more literally would say:

"Let her not be focused on the external world, that of plaiting of hair, and of putting around of things of gold, or of putting on of garments, but -- the hidden man of the heart, in the incorruptible thing of the meek and quiet spirit, which is, before God, of great price"  -1 Peter 3:3-4

Why did the KJV and YLT translate "world" as "apparel" in the above passage?  I can only deduce it may be because it's referring to the worldliness of being overly focused on one's external appearance. Those women who teach that Christian women should be dresses/skirts only are falling into focusing too much on the external.  The Christian woman is to wear apparel becoming of a woman professing godliness, as we saw in our 1 Timothy 2 passage, and that is it.  While a long robe was becoming when the New Testament was written, is is not becoming, now. Dresses can be becoming, and so can pants.

The Bible was written before pants were generally worn, but not completely. The oldest known pants are from very ancient China, long before Christ was born. Later, as horses were domesticated, more and more people began wearing pants.  Imagine riding a horse in a robe, and likely not even with underwear on.  No thank you.

And lest you think pants were only for men, think again.  Those were societal standards in some cultures and times, but not at all in the Bible, and not in all cultures and times.  For example, Greek art from the 6th century shows both men and women Scythian warriors, with both genders wearing pants.

There is nothing wrong with a Christian woman wearing pants.  Further, there is nothing wrong with Dresses Only, if a Christian woman decides to dress that way, but there is something wrong with it, if she tries to make it into a doctrine.