Reworking the wardrobe can really be a challenge yall

Before I begin, you ought to know my 'Fashion' history, although I hesitate to call it fashion because it wasn't. Even though I knew what looked good, and what should and should not go together, I never bothered to emulate any of it in my own wardrobe. As you will see, I have always been about comfort.

When I wasn't in charge of my own clothes, my mother bought me basic colored shirts or flowery prints, and pants - usually slacks.
When I got older my colors delved more into blues, blacks and grays, with the occasional pop of purple or red. I was always a huge fan of distinct jewelry so odd necklaces and dangling earrings were always a part of my wardrobe in middle school, even if they didn't ever go with anything else that I wore.
And then in high school I started my hijab so most of my earrings and necklaces went into storage. My colors were the same for the most part, but I added big sweatshirts to the whole look
a) because I could still wear my half-sleeved shirts that way and wouldn't need to go shopping and
b) do you know how comfortable those things are?? If I could, I would live in them!

Actually, now that I think about it, I kind of did live in those big sweatshirts all through high school..

Anyways, 2009 brought about the first year of college, and my style didn't much change. And when we went to Pakistan that summer of 2010, I had some suits made exactly the way I wanted, and so those became a part of daily wear as well. And that carried over through sophomore year as well.

As you can probably tell by now, I've always been about comfort. And honestly speaking, I was just plain lazy when it came to clothes. My mother had always taught me to wear loose fitted clothes, things that didn't reveal your body in fitting or sheerness, so that was never a challenge to emulate. But beyond that, I was lazy. If it was clean and 'modest' I'd throw it on and walk out.
I never bothered to match or iron anything - hobo hijabi for real yall.

But now, for the first time in practically 8 years, I'm trying to rework my whole wardrobe. And I gotta tell you, it's a freaking challenge.
I know what I want and need, but man, there are an abundance of clothing stores that do not cater to hijabis. Naturally. That's the fact of the matter so no complaining, but this does mean I have to look high and low for my pieces.
My goal for the past couple of months has been to incorporate more dresses and skirts in my wardrobe, and get rid of all of my old slacks, wrinkly shirts, and over-sized sweatshirts.

Ok, I'm lying. ALMOST all. I still want to keep a few professional pants around, and of course my salwar kamiz suits will still be there because those are perfect for me. I had them made super long and loose, but in a dress shape so I don't look like I'm drowning, and I think it would be silly to get rid of them when they work so well for me.
Anyways, so little by little I've been replacing my old closet with a new one, and the reason it's a slow process is because I'm picky in this particular field.

And I'm not picky in the sense you may be thinking. Colors and prints are a free for all. But the modesty check is where I'm picky.
Questions Muslims ask when buying clothes:
Is it long enough to cover my back and front when I sit and stand?
Is it loose enough where the figure isn't being revealed?
Is it solid enough? (Do you know how annoying it is to buy something only to realize it can't be worn because once the light hits it, it becomes glass?? Gawh, it's quite a nuisance).
I don't much ask about colors or sparkly things because thankfully, everyone wears all the colors and glittery things offered in shops, so I feel like that doesn't draw any more or less attention. And the neckline I don't have to worry much about either because there will always be something on top, or under, and then my hijab also drapes over my shoulders so thankfully I don't have to worry too much about that.

If I can't answer yes to all the other three of those questions, I'm back at square one.
And that's the easy part. It's when the answer to the questions are a 'maybe..' or an 'I'm not sure...' that makes the shopping tricky.

For instance, if the dress is long and loose at the bottom, then the top can be managed by covering up with a sweater or cardigan. But is the cardigan too fitting? Can I tie it, or does that make it too snug?
Could I pair this with a long draping hijab?
Etc. Etc.

And I'm getting introduced to some new aspects of fashion in the modern world as well.
Tights would be one of them. Until now, I haven't owned a pair of tights since I was 8 and what I have realized is that tights can give a false sense of security. If the dress worn over the tights is ankle or floor length, then I would say that's decent (and we're talking solid tights, not those weird textured or fishnets ones, I feel like those under a dress defeat the purpose too). But if the dress is knee high and worn over tights, or even skinny jeans, it defeats the purpose. Reason being that, covering doesn't just mean hiding your skin, it means hiding your shape as well.

On a side note rant: honestly, if I could charge a personal vendetta against skinny jeans I would.
Once upon a time jeans were loose, rough and tough products. You wore jeans because they were the common product, they lasted forever, and could be worn by anyone, anywhere, everywhere.
I was never one for denim, but it never bothered me until the skinny jeans fiasco broke through.
now when I think of jeans I think skinny, which is then associated with hipsters, divas, and a false sense of security that they're covering clothes because it's denim when in reality they reveal all of everything by squishing any fat into a lump that pokes out in those forsaken jeans. Girls and guys man, skinny jeans are just not attractive on either. I admit, it's a personal bias, but man do i greatly, GREATLY dislike skinny jeans.

Okay, off that bitter tangent.
So redoing a wardrobe in the modern world can have it's challenges for hijabis.

But the good news is that the challenge only makes it that much more satisfying when something is found. As of this moment I have 3 dresses, all floor length and loose Allhamdullillah. The top is the challenge. I hope that the cardigans worn on top don't make it seem fitted...maybe if I put another layer on?
Idk, I would rather look bulky and square than hint at something else.

Challenges, challenges.

In any case, I'll be doing my best to fit the major criteria.
I'm trying to redo my wardrobe in the first place because, as I'm sure you can tell by what I've already written, I never really cared before. Even now, I'd be hard pressed to say that I 'cared' a whole lot. I just figure I'm in college, I should at least dress my age, and besides that I haven't done American clothes shopping in eons so I figure it's time to clean out my closet.
But even then my laziness breaks through. Give me some long dresses, and a top and I'm done. I cant bring myself to care about matching much, or even ironing. Thank God most of the fabric is the kind that doesn't wrinkle easy xD

Anywho, I've was going through my closet and thinking all these things while I organized so I figure why not share and ask the general public about their closets.
So what about yall? Tell me your fashion history, what does your closet contain most of? When was the last time you redid your wardrobe? and when you shop, what criteria do your clothes have to meet to be purchased?