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How to Make a “Dated” Item Look Modern, According to 3 Stylists

A hallmark of truly great style is the ability to make something old look new–again and again and again–simply by virtue of how you wear it. This is the magic sauce that allows an item or an outfit to remain relevant across decades. Below, we asked three stylists to dig into their closets and find the most “dated” vintage piece, then resurrect it by styling it in a distinctly modern way.


Ryan Gale mixes vintage YSL (blazer and heels) with Urban Outfitters denim

Follow Ryan on Instagram here.

Some background on the vintage hero item: The heels are vintage YSL. I scored these babies at an online auction a little over a year ago. The heel is pretty tiny so I don’t wear them often.

Styling notes: I prioritize comfort over everything, so I’m rocking them with my favorite pair of baggy jeans (I love the oversized pockets on them), a cropped white tank, and an oversized mint green blazer. When shopping for vintage I always pay attention to fabric and material–anything made from silk, leather, or cotton will last a lifetime and never goes out of style. Vintage items that are made from quality fabrics can also be professionally cleaned and altered to look brand new. I had to replace the heel on these, but you would never know.

Favorite places to shop vintage: I find the best vintage pieces while traveling. It’s also really cool to see what others were wearing in different parts of the world. The vintage shops that I can’t get enough of on Instagram are @sororitevintage (they carry an amazing selection of lace intimates) and @fvced_ (her vintage designer collection is truly outstanding!).

Anna Gray updates her ex-boyfriend’s dad’s super-slim shirt.

Stylists Make a Dated Item Look Modern
Vintage striped shirt, vintage snake pant — another here and here, vintage silk mule — others here and here, vintage Celine pony hair bag — another here and another option here, vintage sunglasses — similar here, Lorod T-shirt, Studs earrings

Follow Anna on Instagram here, and check out Object Limited–the online vintage marketplace she co-founded!–here

Some background on the vintage hero item: The striped shirt is an ex-boyfriend’s dad’s silk button down from the 70s. It doesn’t look old until you get into the details, like the pointed collar, fraying edges, french cuffs, and slim fit. It’s the perfect shirt. The weight, width, and cream/navy stripes go with everything–all denim washes and jewel tones, and it can be tucked or left open or worn closed. If I believed in making instead of finding, I’d have this patterned so I could keep making new ones as this one wears out. I wear it all! The! Time! Plus, there’s something funny and nostalgic about keeping an old boyfriend’s clothes. He’s probably going to see this and want it back.

Styling notes: I find that mixing prints is the fastest way to say “I’m trying with my outfit” without actually trying. The vintage snake pants are the right colors with the shirt so the outfit looks purposeful (organized?) rather than clashing. The trick to this is to step away from the mirror and squint. Do the colors complement one another? If yes, then we’re good to go. The rust-colored shoe has warm tones that work with the vintage Celine bag and the hint of blue in the Lorod T-shirt keeps the whole thing from being too dull. The lazy stuffed tuck and rolled sleeves keep the whole thing casual and easy. Also! Worth noting that tailoring pants can be a good idea! Everything looks tidier when it fits.

Other tricks for making vintage look modern: don’t wear all same-era. My 70s shirt is paired with Y2K pants, a contemporary shirt, a 90s bag and a shoe style that originated in the 18th Century (but reads very 1950s these days)!

Favorite places to shop vintage: Object Limited!!! We have so many vendors that cover the full spectrum of aesthetics from goth-grunge to Martha’s Vineyard to 90s Italian fashion. Scrolling through the app is like zooming through every well-curated vintage store in the world. Outside of Object, I try to find sellers that clearly, deeply love digging through people’s “old” clothes and finding the gems. It’s interesting to think about resellers as the answer to the fashion world’s overproduction issues. Department stores are failing because it was only up to a few buyers to decide what shoppers would want in six months. Now vintage sellers have so much power, from where they list their items to how they style them to what they choose to buy. It’s cool and feels very nuanced and democratized! And as consumers, we have more options for sustainable shopping, inspiration and community. My Favorite vintage stores are Maj Kiosk, Wayward Vintage, Nanin Vintage, Michaela Co, Subrina Heyink, and Lucia Zolea!

Courtney Madison finds the perfect, flouncy blouse at a Canadian thrift store.

Follow Courtney on Instagram here.

Some background on the vintage hero item: I’ve had this blouse for about 12 years. I bought it at a thrift shop in Canada called Value Village which is like a Goodwill. When I bought it I was working at a high-end menswear store and the dress code was a white shirt and black pants/skirt/jacket. I chose to interpret this shirt as appropriate for the dress code and my boss never corrected me. Now I probably only wear it a couple times a year to a dinner or something, occasionally buttoned all the way up with ruffles and shoulder pads on full display. The polka dots are actually hexagons, one of many special details that make it a pretty memorable piece!

Styling notes: I styled the blouse with a favorite pair of trousers by Nanushka (high waist, wide leg and super lightweight), a barely-there sandal, and classic gold accessories. Unless you’re wearing a two piece set and really going for it, I think the best way to modernize vintage is to pair a statement piece with something more obviously contemporary. If everything you have on is reminiscent of a specific time period, you can run the risk of looking like you’re in costume.

Favorite places to shop vintage: My favorite LA vendor is @marketvintagela, my favorite LA stores for unique pieces are @cannonballandtilly and @recessla.

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