My original plan for this outfit was simply to wear the grey wrap dress as a duster over this green shirt dress I have. I thought it would work as the reverse of the dress and military jacket look I wore on Day 1. But the shirt dress is a high-low cut, and I really didn’t like how short it was on me in the front. So I decided to throw this pleated skirt on over top, and I’m so glad I did, because this may be my favorite outfit yet! (Yes, even more than the jumpsuit.) And yes, the front of the shirt dress was cut even shorter than this skirt. Waaay too short for my comfort zone. But the skirt is pretty much the perfect length to really make my legs look long.

And because I really didn’t want to disrupt the navy waistband of the skirt, I opted to just tie the straps of the dress as duster in the back as a loose bow. It still gives me the duster effect, but without losing the way the skirt actually emphasizes my waist. (And if you’re keeping score, that’s now four different ways I’ve tied the dress as a duster.)

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A few days into the challenge, a friend of mine hinted that she thought we’d see a leather jacket coming up in the future. And while it seems like an obvious choice, I’ve never really been a leather jacket wearer. And since one of the rules I set for this challenge is that I’m trying not to buy anything new, I figured it wouldn’t happen. But then I remembered this faux leather jacket I had bought years ago for a model photo shoot.

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As soon as I styled yesterday’s look, I knew it was going to be a challenge to top it. So I’m not even going to try. Instead, I’m following it up with a look that I’m not totally sure about. But as I mentioned in another post where I wasn’t sure how I felt about the outfit, part of the creative process is that you have to try a lot of things, and not every result is going to be a slam dunk.

In the case of this outfit, my goal was to try something a little bit different. It would be really easy to just keep wearing the wrap dress as a duster over other dresses I own (because I really love the way that looks), but that feels like cheating the creative process. So I’m pushing myself to experiment with different ways of layering the dress, which in this case, means putting a tank top over it.

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When I was a kid, my mom would never let us shop at Old Navy, because she said that all the clothes always got super wrinkly. She may have had a point with this linen jumpsuit, but I’m willing to overlook any wrinkles because I actually managed to find a jumpsuit that is flattering on me. And the wrap dress over top just takes it to a whole other level. If I ever have to fight crime, I’m totally doing it in this outfit. (And yes, that includes the chunky heeled boots and bold Contra necklace!)

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This black and navy strapless striped dress may be one of my favorite summer dresses, (I actually like it so much, I own it in a few colors, but the stripes are my favorite.) and I love how wearing the wrap dress as a duster let’s me extend this dress into colder weather.

Because I really like the way the striped dress gives me a waist, (which doesn’t always happen for me) I decided to experiment with tying the wrap dress a slightly different way. I started by tucking the belt under the wrap dress and then tied it just around the dress underneath. (When you’re styling the same dress thirty ways, you start to look for little details you can change!)

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After my foray into color yesterday, I couldn’t resist styling today’s look with just the dress and oversized charcoal sweater. To mix things up, I added a second belt over the sweater to help give it more shape. (Side note: now all I can think about now is that episode of Friends where Gary Oldman plays Joey’s co-star in a movie, and he shows up to work drunk and slurs “I’m wearing two belts.”)

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I really wanted to just toss this charcoal cardigan on over the wrap dress and call it a day. (Because tossing on a cardigan is pretty much my go-to solution both for keeping warm and for adding vertical lines to an outfit.) But after looking at my outfits for the first seven days of the challenge, I thought maybe it was time to add a bit of color.

I decided to layer on this aqua (teal? turquoise?) skirt that I’ve had for a while, but never really worn because I wasn’t thrilled with the length or thinness of the material. But it’s perfect for adding a pop of color to this outfit. (And can we all just agree to pretend it’s not so wrinkly. I have no idea where my iron is!)

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Today’s outfit is pretty much as comfortable as it gets, as I’m layering this cozy wrap dress over this oversized grey and black stripe knit dress that was already pretty much the most comfortable thing in my closet. And I love how the result ends up being kind of playful, with the vastly different hem lengths and the the striped sleeves sticking out underneath. (But at the same time, still kind of badass with the short hem of the under dress and chunky boots.)

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Today’s outfit has me channeling my inner film vixen. Like Sophia Loren or Marilyn Monroe. Or if we’re being totally honest, Maureen O’Hara in the second half of the original Parent Trap. (Which I may have watched six times in the week between Christmas and New Year after I found out it was leaving Netflix on January 1st. Not to mention the probably thousand times I watched it as a kid.)

Actually, the original Parent Trap has a lot to offer in terms of style inspiration. As a kid, I envied the outfits worn by the twins. (That yellow dress and sweater that Sharon wears getting off the plane in California was always my dream.) But watching it again now that I’m older, I have a newfound appreciate for the looks the mother wears. (When she becomes a California style icon, not a matronly Boston mother.) And I can see how some of that rubbed off as I was photographing today’s look.

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Of all the looks I’ve styled so far, I can’t say this one is my favorite. While it does make for some interesting detail around my face, neckline, and sleeves, I don’t think it does enough to break up the grey mass of the dress. (Even with the addition of the black belt to break it up.)

But I decided to post it anyway, because I think this is an important part of the creative process. When you do this kind of challenge, not everything is going to be a slam dunk. What’s more important is that you’re trying lots of different ideas.

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