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How to Wear Vintage Clothing and Accessories | 2020

8 Style Hacks I Swear By For Making Vintage Pieces Look Fresh and Modern

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My interest in vintage fashion has ebbed and flowed over the years. In high school, one of my most prized possessions was a pair of vintage Chanel aviators that may or may not have been real (I preferred to think the former). In college, I was all about the dig at places like Buffalo Exchange and local thrift shops. Since moving to New York, I've done some serious damage at outdoor bazaars and my favourite local haunt, Housing Works (a nonprofit thrift store with locations throughout the city), happening upon designer gems like an ankle-grazing Gucci leather coat, a pearl-and-rhinestone-adorned Max Mara jacket, and many no-name treasures from leather pants to oversize blazers and costume jewellery.

Right now, I'm in a major flow period when it comes to vintage clothing and accessories, which means my shopping tactics have taken to the interwebs. I love re-commerce sites like The RealReal and Vestiaire Collective where I frequently search for designer accoutrements like belts, boots, and coats. When it comes to pre-loved luxury goods, places like Fashionphile and What Goes Around Comes Around are absolute treasure troves (both with reputations for a thorough authentication process). I even love the occasional eBay or Etsy binge (you can count on both these sites having incredible deals on way-back fashion).

With circular fashion and the part it plays with regard to sustainability being a top topic these days, I've become more eager than ever to showcase my vintage shopping prowess. Lately, I've been swarmed with questions from friends, co-workers, and Instagram connections on where I find my best pieces, how I select products, and my tricks for making every piece feel modern and not outdated. So, I'm spilling some of my secrets by way of eight vintage pieces I wore to New York Fashion Week this season. While I didn't wear vintage head-to-toe, I made a concerted effort to style every outfit around a vintage piece I loved.

Scroll on to see how I did. Plus, shop some of my exact pieces as well as similar styles to recreate any one of these outfits on your own.

The Vintage Piece: Leather Pants

I found these vintage leather pants at Housing Works for about $15 with no label and several pre-loved markings (which hardly show). With a straight-leg fit, they look sleek and modern all on their own, but especially so with oversized blazers and cool knits.

The Vintage Piece: Leather Pants

Giving my best fashion-girl meets '80s-business-chic, I paired these vintage leather pants with an oversized checked blazer, thin turtleneck, and white patent boots for a sleek result.

The Vintage Piece: Leather Pants

The final piece? A two-tone tan bag from one of my favourite new labels, Polène.

Versace Pre-Owned Leather Straight Jeans

Versace Pre-Owned Leather Straight Jeans ($553)

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The Vintage Piece: Leather Pants

See? I told you I love these pants. Which is why I wore them a second time, this time with another vintage piece — a Chanel jacket I sourced from What Goes Around Comes Around. A total classic, I love the way this pea-coat style hangs alongside my leather pants, not to mention over a fairly thick sweater from 3.1 Phillip Lim.

Image Source: Style Du Monde

The Vintage Piece: Leather Pants

Because both my vintage pieces were dark and muted, I opted for a colourful bag — this one is from the eco-friendly brand, If I Fell — and my go-to white ankle boots with a slightly sculptural heel.

Image Source: Style Du Monde

Chanel Wool Knee-Length Coat

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Leather Straight Pants

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The Vintage Piece: A Bag

Another What Goes Around Comes Around find? This checkerboard print bag from Louis Vuitton. With an almost dizzying effect (in a good way), I kept to solids with the rest of my outfit, choosing a belted patent jacket and brown leather pants.

Image Source: Style Du Monde

The Vintage Piece: A Bag

Being fashion week and all, I couldn't help but experiment with a little pattern play. Enter: these snake-print boots by one of my go-to shoe brands, Schutz.

Image Source: Style Du Monde

Louis Vuitton Damier Ebene Alma PM Bag

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Frankie Shop PVC Jacket

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Schutz Maryana Boot

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Image Source: schutz-shoes.com
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The Vintage Piece: A Bag

Another bag! This time, a classic black Chanel from Fashionphile. Isn't she pretty?

The Vintage Piece: A Bag

I love a good slip dress and often stick to neutrals, so this zebra-print silhouette was my perfect cold-weather version to pair with my vintage Chanel or Fashion Week.

The Vintage Piece: A Bag

For a fresh finish I added in a pair of knee-high boots in optic white.

Chanel Lambskin Quilted Small Double Flap Black Bag

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Image Source: fashionphile.com
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Sam Edelman Hai Boots

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Image Source: zappos.com
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The Vintage Piece: Boots

Up until this month, I've weirdly not owned a pair of black suede boots. I went ahead and solved that problem by scooping up these vintage Gucci boots from Vestiaire Collective. Not only are they outrageously comfortable, but, like my Chanel bag, they're a total classic.

The Vintage Piece: Boots

For a wearable take on the oversized dressing trend, I teamed my boots with a vegan leather shirt jacket, grey turtleneck, and pleated skirt, which, is also vintage! More on that later.

The Vintage Piece: Boots

A detail shot, because, how could I not?

Gucci Black Suede Boots

Gucci Black Suede Boots ($290, originally $359)

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The Vintage Piece: A Skirt

OK, now we're ready to talk about my skirt. This vintage Issey Miyake style is another What Goes Around Comes Around find that also happens to be totally on-trend for Spring. Say it with me, circular fashion! To ensure my look wasn't overly feminine and not totally impractical for the rainy day I wore it on, I love the juxtaposition of the oversized leather shirt and tall boots that would peek out every so often from my slit.

Pixie Market Black Vegan Leather Shirt

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Image Source: pixiemarket.com
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C by Bloomingdale's Cashmere Turtleneck Sweater

C by Bloomingdale's Cashmere Turtleneck Sweater ($70, originally $178)

Image Source: bloomingdales.com
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Issey Miyake Pleated Accents Midi Length Skirt

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Image Source: therealreal.com
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The Vintage Piece: A Skirt

One more time for the bag, yeah?

Chanel Lambskin Quilted Small Double Flap Black Bag

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Image Source: fashionphile.com
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The Vintage Piece: A Belt

I'm majorly into belt rights now, likely because I've been influcend a number of glorious styles put out by Daniel Lee for #NewBottega. I found this vintage Gucci horse-bit belt on Vestiaire Collective and bought it with the intention of wearing it over a coat (it was two sizes larger than I'd normally go for).

Image Source: Style Du Monde

The Vintage Piece: A Belt

By sticking to clean and tailored pieces like my wool coat and tall boots in a graphic black and white palette, this vintage belt moment felt super modern and fresh on a drizzly day.

Image Source: Style Du Monde

Gucci Leather Horsebit Belt

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Image Source: therealreal.com
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Image Source: aritzia.com
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The Vintage Piece: A Belt

Clearly I like to do things in twos, which is why I gave another vintage belt a try. This time? A chainlink Chanel style I borrowed from Switch — a membership site where you can borrow vintage pieces with the option to buy styles you love depending on your membership.  

Image Source: POPSUGAR Photography / Dana Avidan Cohn

The Vintage Piece: A Belt

Though it's subtle, I loved styling this belt over my trench coat for an unexpected accent. There's something about a dangling CC emblem that makes even the simplest of outfits feel so much fancier.

Image Source: Style Du Monde

The Vintage Piece: A Belt

As you can see, my vintage Gucci boots and Chanel bag came along for the ride.

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Chanel Lambskin Quilted Small Double Flap Black Bag

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Babaton Torino Double-Breasted Trench Coat

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