This is my third time wearing this plaid shirt for the challenge, and it’s definitely my favorite version yet. I love how simply wearing it on top of the dress allows the bold black and white pattern to pop, and I love how rolling the shirt to the waist of the dress gives it the feel of a long skirt.

I did realize that the challenge of this dress is that, because it has such full sleeves, it makes it super difficult to actually layer another shirt on top. (There’s a lot of scrunched up fabric on my upper arms which I’m pretty much just choosing to ignore.) However, I love the idea of this look. (And the potential for the several other flannel shirts I own that I’ve never quite figured out how to style properly.)

So my first order of business when this challenge is over is to get myself some sweatshirt fabric and attempt to make myself a wrap skirt that emulates the bottom of this dress. If it works out like I envision in my head, I’ll definitely be sharing more than a few outfits here on the blog. (And hopefully making it in more than one color!)

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I really wanted to give this purple cardigan another go, because I love the color (both on me and with the grey of the dress), but didn’t exactly love the way I styled it the first time around. Since I didn’t quite love the way the cardigan laid on the bottom half of the dress, I opted to add the black metallic pleated skirt to the mix. (Which now makes four appearances for that skirt, clearly it’s becoming a workhorse in this challenge!) I also decided not to get fancy with the ties this time, and simply wear the cardigan over the dress and skirt combo.

The result is an outfit that’s seriously cozy (a sweatshirt dress and cardigan!?!) with just a hint of glam in the skirt. I also used my safety pin trick again on the bottom of the wrap dress, so that it didn’t stick out under the skirt.

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I knew I wanted to wear this pleated skirt at least one more time for the challenge. (Because I love the length, the color, and how long it makes my legs look!) My original thought was to simply wear it with a blue velvet cardigan (like I did here) and the duster over top, but since I’m trying to think about how I can rework pieces I’ve already worn in the challenge, I did a quick inventory, and decided to wear it over this strapless dress from Day 10.

I love how the colors of the strapless dress and pleated skirt compliment each other, while the stripes running in opposite directions create some visual interest. (And the wrap dress as duster just serves to make these summery pieces more appropriate for colder weather.)

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I brought this ikat shirt back from my last trip to India, and ever since I started my one dress challenge, I’ve been trying to make it work. I keep putting it on over the dress, deciding I don’t totally love it, and then taking it off. It just always seemed like it needed something more. Enter the military vest, which is quickly becoming the go-to piece in my wardrobe for making a look feel complete. (I’ve now worn it three times in this challenge!)

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This is one of the outfits that I only feel ok about. I love the purple color of the cardigan with the grey dress (and with my hair) but I tried to get all fancy and tie the belt of the dress over the cardigan, and it just didn’t work out as planned. I think if I were to wear this again, I’d just tie the belt on the dress the regular way, and throw the cardigan over top.

Or I might spend a little more time experimenting with a few other ways to tie the belt/dress until I found something I liked better. That’s the thing with the creative process (even when it comes to style). Sometimes you nail it on the first try, and sometimes you have to finagle it until it works!

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I can’t believe I’m now 2/3 of the way done with this challenge! For today’s look, I once again wanted to remix pieces I’ve previously worn throughout the challenge. I opted for the wrap dress as duster, with the plaid shirt I wore under the dress on Day 5 and the metallic black pleated skirt I wore on Days 3 and 6.

I love how the plaid shirt helps dress down the metallic skirt. (Which makes it a great way to take the skirt I bought for the holidays casual enough to wear through the rest of winter!)

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For today’s outfit, I thought it would be fun to remix a few pieces from previous outfits into something new. (As I mentioned when I first set this challenge, this isn’t about a capsule wardrobe. My closet is pretty extensive. But I do think it’s a good exercise to think about remixing previously worn pieces, rather than constantly defaulting to something different to wear with the wrap dress.)

Since I first wore the printed skirt (made from fabric I designed), I knew I wanted to wear it again with the wrap dress as a duster. My normal default for that skirt is to wear it with a black top, but I loved how much the teal sweater from this outfit works with my refreshed hair color that I wanted to pair it with the skirt. The result is more color and pattern than I usually wear, but in an outfit that still really feels like me!

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Can we talk about how many pockets this outfit has?!? There are pockets in the vest! There are pockets in the skirt! AND there are pockets in the dress! (Not that you can easily access them under the skirt, but still, there are pockets! And they would be an amazing place to keep something secure.) This is seriously more pockets in one outfit than I ever thought possible. (At least, without wearing pants.)

And yes, I’m wearing the military vest again. Because when I rediscover a piece in my closet, I tend to make it a go-to for a while. But this time, I’m layering it over the skirt I wore on Day 2. I think it’s a great way to add a little attitude to the sweetness of the skirt.

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Today’s outfit is another attempt to inject some pattern into my looks for this challenge. My original plan was to wear a skirt over the patterned dress (kind of like I did with this look) but I ended up really liking the printed dress on it’s own with the wrap dress as a duster over it. I think the fact that it snowed this week (and that it’s now magically wintery white outside instead of just gross and brown) has me really feeling the white, navy, and grey color palette of this look.

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Every since I started this one dress, thirty ways challenge, I’ve been wanting to style a sweater over the dress like my friend Stasia, who is a master at wearing sweaters over dresses. But the reality is, Stasia and I are built completely differently, and every time I pulled on a sweater over the dress, it only ever looked ok. The reason for this is that I have broader shoulders than Stasia, so while she needs width up top, I tend to look better with styles that have vertical lines. (To break up my broad expanse of chest.) This is why the wrap dress as duster thing works so well on my body.

Still, I was determined to successfully style a sweater over the wrap dress. And then, I unearthed this military vest from the back of my closet. I actually originally thought about just wearing the vest over the dress, but it came off a little blah. But the sweater adds a pop of color and the vest adds the vertical lines to make this an outfit that really works for me. (Plus, it helps that I just got my hair colored. Vibrant red hair makes anything pop!)

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