The $30 Thrift Find That Rekindled My Love of Styling

Sustainable Clothing | Wardrobe

This post may contain links to shops that I regularly support and am affiliated with. Read my About Page or my Disclaimer for more information.

The $30 Thrift Find That Rekindled My Love of Styling


Sustainable Clothing, Wardrobe /

This post may contain links to shops that I regularly support and am affiliated with. Read my About Page or my Disclaimer for more information.

Finding My Vintage-Inspired Style (Again)

“I’d rather die than wear a midi-length denim skirt.” At least that’s what I assume my teenage self would have probably thought about it. But it turns out, a midi-length denim skirt was exactly what I needed to help me see my wardrobe, and myself, with a fresh set of eyes. You see, after working a corporate job, moving uptown, getting pregnant, and raising a baby, my wardrobe has been through many transitions. If I shift through my closet, I can find fragments of the bold fashion choices I used to make. And for a while, I was happy to stick to ”safe” and took on a more classic approach to my personal style.

I had spent an other morning sifting sadly through the few items in my closet that would accommodate this new post-baby body. My waist has yet to return to it’s former dimensions (26”) and I don’t know if it ever fully will. After wearing the same 12 pieces of clothing (not counting athletic wear) for 10 months, I was feeling uninspired and slightly ashamed. When was I going to be able to slip into my summer dresses without feeling like a seam might burst? My fitted skirts? My-gaspjeans???

Thankfully after a bit of digging, I discovered a lemon yellow skirt discarded toward the back of my closet that fit my slightly roomier belly just right. (And I actually really like the outfit I came up with that day.) That got me thinking: why was I being so closed minded about what I need to wear at this stage of my life? Why not incorporate something new and reinvigorating? And by ”new”, I mean ”old” since I am still under the buy nothing new challenge.

I’ve been yearning for something different. Something that felt more ”me” right now. I wanted to feel playful with my clothes again. Determined to source some inspiration, I ventured deep into the heart of Toronto’s colourful Kensington Market. I didn’t know what I was looking for, but I was confident something would click. Not only that, I was dieing to get my hungry eyes into the racks of vintage clothes at some of my favourite used clothing shops.

Finding Inspiration

It boldly struck me on the street that day. Coffee cup in hand, she crossed the street infront of us looking effortlessly cool. A girl with her hair tossed into a messy bun wearing worn tennis shoes, a white t-shirt, and a button-up denim pencil skirt worn half open. ”Ah ha!” I thought, “That’s exactly what I need right now! A denim skirt.” I’d never owned one before, as they seemed like an intimidating piece.

At the time of writing this, I knew it would be easy to find short denim skirts. However, I was not going to settle for a denim mini skirt. For various reasons, it would need to be midi length. And from past experience, I know that I prefer midiskirts that button all the way up so that I can create a slit effect. (Anything to help a short gal look a little taller!)

This was quickly becoming a rigid set of criteria. Where does one even find midi length, button-up denim skirt these days? They certainly aren’t on-trend right now and haven’t been for a few decades.

So I headed to the place where all great fashion trends await their victory lap: the thrift store.

The Thrifty Mindset

As a seasoned thrift shopper, I certainly wasn’t confident that my initial hunt would be successful. Going into a secondhand shop with a specific item in mind, and expecting to find it that day, almost never happens. More often than not, it will elude you. Instead you will find similar items that are either the wrong fabric or the wrong size. Because of that, it’s always best to approach secondhand shopping with a general concept instead of an exact image.

How to Hunt for Elusive Vintage Pieces

But how do you approach vintage hunting when you have your heart set on something specific? I’ve been there. In fact, this was my exact situation in the search for the elusive denim skirt. Here are some tips and things to keep in mind:

  • You should anticipate needing to visit several stores (either online or in person) and checking back more than once. I have an article about my favourite vintage and secondhand shops.
  • If you’re using Vestiaire Collective or ThredUP, you should setup alerts based on specific criteria. (ie: your size, fabrics, colour, price range, and even specific brands.)
  • For physical shops, talk to the staff. They can let you know when to predict new shipments or if they have items tucked away in storage.

The Vintage Denim Skirt

Kensington Market was buzzing with street performers, live music, and plenty of people looking to spend a sunny Sunday on an outdoor patio. Thankfully that meant the longstanding vintage shops weren’t horribly busy. Exile Vintage sits almost in the center of Kensington Market and has always had a great denim selection. After sifting through several racks of well-worn Levis, I start to wonder if I’m searching for something that doesn’t exist. But then in the back of the store, hidden behind a maze of bizarre retro dresses, I find a small selection of skirts. And there it was: a midi length button-up denim skirt in. my. size.

How to Style a Vintage Denim Skirt

It seems the thifty gods were smiling on me that day, because it is indeed rare that you find exactly what you are hunting for in the first shop you visit. I excitedly waved the skirt at my husband, who gave me that exasperated yet patient ”I don’t understand why this brings you joy”-look. It’s worth pointing out that he’s a novice when it comes to styling. So I can excuse his lack luster response.

When incorporate vintage pieces into your existing wardrobe, you need to have a good eye. It’s, dare I say, an acquired skill. And I think that may be why many people shy away from it. But fear not! It’s way more simple than it seems. When it comes to styling vintage, there are just as many rules to break as there are to follow. (And I could probably dedicate several articles to that alone.) But in general, I like to stick to this guide when dressing myself: something modern with something vintage. This keeps your look more model off-duty and less dusty pawnshop.

There are so many ways to style a denim skirt. My mind started racing with the possibilities as soon as I scooped it up from Exile. Here are just a few ways I’ve done it recently:

Shop My Outfit

Kosas Air Brow Tinted Volumizing Treatment Gel
Kosas Air Brow Tinted Volumizing Treatment Gel
Kosas Wet Lip Oil Gloss
Kosas Wet Lip Oil Gloss
ThredUP – browse denim skirts – save $10
ThredUP – browse denim skirts – save $10
Vestiaire Collective Missoni Sunglasses – save $50 ‘USX53P’
Vestiaire Collective Missoni Sunglasses – save $50 ‘USX53P’
Call It Spring Floraa Mule
Call It Spring Floraa Mule
Vestiaire Collective YSL vintage sunglasses – Save $50! ‘USX53P’
Vestiaire Collective YSL vintage sunglasses – Save $50! ‘USX53P’
Vestiaire Collective Stella McCartney Falabella Tote – Save $50 ‘USX53P’
Vestiaire Collective Stella McCartney Falabella Tote – Save $50 ‘USX53P’
Stella McCartney Falabella Pochette Shoulder Bag
Stella McCartney Falabella Pochette Shoulder Bag
MATE Organic Cotton T-Shirt
MATE Organic Cotton T-Shirt
Kosas Air Brow Tinted Volumizing Treatment Gel
Kosas Air Brow Tinted Volumizing Treatment Gel
Kosas Wet Lip Oil Gloss
Kosas Wet Lip Oil Gloss
ThredUP – browse denim skirts – save $10
ThredUP – browse denim skirts – save $10
Vestiaire Collective Missoni Sunglasses – save $50 ‘USX53P’
Vestiaire Collective Missoni Sunglasses – save $50 ‘USX53P’
Call It Spring Floraa Mule
Call It Spring Floraa Mule
Vestiaire Collective YSL vintage sunglasses – Save $50! ‘USX53P’
Vestiaire Collective YSL vintage sunglasses – Save $50! ‘USX53P’
Vestiaire Collective Stella McCartney Falabella Tote – Save $50 ‘USX53P’
Vestiaire Collective Stella McCartney Falabella Tote – Save $50 ‘USX53P’
Stella McCartney Falabella Pochette Shoulder Bag
Stella McCartney Falabella Pochette Shoulder Bag
MATE Organic Cotton T-Shirt
MATE Organic Cotton T-Shirt

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