I wore the same dress all week—here's what happened

Hilary Hagerman
Managing Editor
Wool& Brooklyn Wrap Dress

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Can we entirely change the way we dress?

That’s the question clothing brand Wool& is asking their consumers. The conscious, sustainable brand, which designs easy-to-wear, capsule wardrobe-ready dresses made from merino wool, recently challenged 50 people to wear their Rowena Swing dress for 100 days in a row.

As a former fast-fashion driven shopaholic, I’ve been looking for ways to pare down my wardrobe to more wearable, sustainable basics that I can wear year round. It hasn’t been easy—and I’m still tempted by the ever-churning cycle of what’s new at H&M or Zara—so I was especially intrigued by the brand’s challenge.

Basically, as they put it, the ethos behind the challenge is to encourage shoppers to “find contentment with less.” But they also say they aren’t pushing minimalism. They’re not not going to limit how many clothes you buy, or what you shop for, or change what you like. But by creating a dress from merino wool, a performance fabric that doesn’t wrinkle, regulates temperature, breathes and needs to be washed way less than most other fabrics (hello, odour resistance), the goal is that they’e making it easier to wear and re-wear the same basic piece that seamlessly blends in with your life. 

While the 100 Day Challenge featured the Rowena Swing dress, another dress on the Wool& site caught my eye: the Brooklyn Wrap Dress. At $128 USD, the dress features a cinched waist, a wrap front and a boatneck back, which allows it to be worn both frontwards and backwards. 

The Brooklyn Wrap Dress, Wool&

Wool& Brooklyn Wrap Dress

$169 ($128 USD), Wool&

I snapped this up in black and while I wasn’t quite ready to participate in the full 100 Days Challenge, I was inspired by my coworker Kate’s capsule wardrobe challenge and decided to challenge myself to wear the same dress to work every day for a week. 

Day 1:

Day 1's outfit featured two pieces from another of my favourite sustainable brands, Tradlands.

On the first day of the challenge, I kept it simple, by wearing the Brooklyn Wrap Dress with a pair of black tights and my Alexander Wang booties. It was a cooler fall day, so I combined the look with two pieces from another one of my favourite sustainable brands, Tradlands: the Shelter Cardigan in Birch and the Chore Coat in Burnt Sienna. This look felt basic and put together without being too boring.

Day 2:

My least favourite look of the week.

The second day was a disgusting, rainy, cold day and left me feeling frumpy, and thus, led to my least favourite look of the week. Since it was chilly, I threw an old, oversized H&M sweater over top of the dress, and belted it with a vintage Gucci belt. While walking to work, I wore my Isle Jacobsen rainboots, and once inside the office switched them out for one of my favourite pairs of shoes: Sezane’s Eugenie with velvet laces.

Day 3:

Day 3's outfit had me feeling most like myself.

This might have been my favourite look of the week—or at least the look that felt most “me.” It was a warmer day so I kept things simple by wearing the dress backwards and belting it with a western-style belt to accentuate my waist. Again, I paired it with my Alexander Wang boots (which by the way, have been a favourite for about 5 years. One of my first investment pieces I know I’ll wear for years to come!)

Day 4:

Day 4's look featured a printed midi skirt and an oversized denim jacket.

This was another favourite look, because it was such a good example of how creative you can actually get with the same piece. I paired the Brooklyn dress with a silk leopard midi skirt to give it the illusion of being a chic wrap top. I combined it with an oversized denim jacket and finished things off with a pair of my favourite flats, Everlane’s Day Glove in mocha (seriously, these are the most comfortable flats ever. I own four pairs!)

Day 5:

On day 5, instead of keeping warm with a cardigan or sweater, I layered a lightweight turtleneck underneath the dress.

The last day of my challenge was a bit chilly and dreary, but I didn’t feel like doing the dress/cardigan or sweater over dress combination I had done earlier in the week. So instead, I added a lightweight grey turtleneck underneath. I combined it with an old pair of brown Salvatore Ferragamo boots.

So, what did I learn from the challenge? Truthfully, I don’t think wearing the same thing every day is necessarily for me—but again, that’s not the point. It made me more conscious about choosing my outfits and how I could do more with less. Plus, it also allowed me to pull out some pieces from my closet I haven’t worn in quite awhile as complements, further proving the value of high-quality basics and being more mindful of consumerism.

One of my biggest worries was what my colleagues would say. As the managing editor of Yahoo Canada’s Lifestyle site, I take pride in my outfits, so I felt like it might turn heads if I wore the same thing all week. But the few who did notice (which, besides my direct team, was really only people I meet with multiple times a week) mostly commended me on my mixing and matching and ability to create different looks. No negative feedback at all, which is a great reminder that people probably care less about what you’re wearing than you think they do. 

The dress itself held up beautifully. As evidenced by my outfits, the weather swung from chilly and dreary to warm and sticky. I didn’t wash the dress the entire week and by Friday night there was no scent, no wrinkling, no signs of wear. Since I did the challenge I’ve worn this on a few other occasions and still haven’t washed it. This dress seriously doesn’t wear, and I know it’ll be a basic I turn to season after season. 

In hindsight, I think I might have leaned towards the Rowena Swing dress if I was re-doing this challenge. While the wrap style is so flattering and versatile, it’s definitely a little more limiting in the cooler months where the long-sleeved A-line silhouette of the Rowena is one I could see myself wearing year round with no issues.

If you’re interested to shop the Wool& dresses, you can check them out here.

Would you wear the same thing for a week, or more, 100 days? Let us know in the comments below.

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