How to Shop and Style Vintage to Look Modern and Cool: 10 Tips From Vintage Aficionado Anna Gray of Object Limited

Words by Jody Hume | 6.22.20

“We’re a company founded on the principle that nothing needs to be purchased new (except maybe socks and underwear). I haven’t bought anything new in almost two years,” proclaims Anna Gray, the Creative Director and Co-founder (along with Co-founder Rudd Taylor) of Object Limited. Hailed as “The Ultimate Vintage App” by Vogue Magazine, the two-part retailer launched in 2018 is an e-commerce platform to buy and sell high-quality vintage goods as well as offer a physical experience at pop-up bazaars. 

For Gray, a fashion vet and vintage-obsessive, the idea for Object Limited developed during a two-week cross-country trip from New York to Arizona that Gray embarked on in 2018, stopping at every vintage shop, thrift and flea market across the country, honing her eye and expertise along the way. “Did you know that there are more brick and mortar secondhand shops in the US than Starbucks? It’s true!” she declares. Gray has perfected the subtle art of mixing vintage with contemporary pieces for an era-fluid style that looks effortlessly contemporary and chic, making her the industry’s go-to for advice. “I’ve always worn vintage because it’s usually less expensive and weirder and I like saying, ‘thank you it’s vintage!’ because I have a style superiority complex.”

Shopping for vintage clothing is not for the faint of heart. It requires a keen eye and tried and true expertise perfected from years of sifting through decades-old clothing. The risk? If you’re not careful, you can wind up looking like you shopped your grandmother’s closet rather than perfecting a chic Instagram-ready outfit. So what’s the appeal of shopping vintage then, you ask? The thrill of the find. And does the gain mitigate the risk? Vintage savants can attest to the dopamine rush obtained by scoring gems from bygone eras, such as a Jean Paul Gautier printed embroidered sheer top from the 90s found sandwiched between a heap of polyester tops. Or fashion diehards recognizing a rarefied piece from Tom Ford’s Gucci era. 

Acquiring vintage means owning a little piece of fashion history, offering a glimpse into a bygone era. It’s an exhilarating feeling to add a treasured item to your wardrobe, readily waiting to be mixed and matched. Shopping vintage can also guarantee uniqueness — you won’t see your finds plastered all over Instagram. The cherry on top? Shopping pre-loved through consignment or vintage is inherently sustainable.


But how can you locate the gems and style past-era items in a fresh and modern way? 


Rest assured, you don’t have to be an expert to dip your toes into the world of vintage shopping. We’ve got you covered. The effortlessly chic Anna Gray is on hand to help us out. Not one to talk the talk, but not walk the walk Gray also shows us how it’s done with her weekly “How To Wear Stuff” series, (via Object Limited’s Instagram and App), featuring Gray tackling a new styling challenge in every episode. Tune into this week’s episode to see Gray styling vintage pieces scored from The RealReal.

We’ve determined that there are two main lessons to take with you on your vintage journey. One: how to spot a needle in the haystack of vintage gems, and two: how to style vintage pieces in a modern way. Gray’s tips and time-honored tricks of the trade are below:


On Where To Start For Vintage Neophytes

“Personal style in general is an ongoing exploration of what makes us feel good and vintage is exactly the same. So, experiment! Plus, you can always put something back into the ecosystem of resale for someone else to love! It’s all about styling.”


Fabrics To Look For

“I try to buy 100% silk, cotton, wool, leather, biodegradable pieces. But if it’s non biodegradable synthetic and amazing it’s better to have it live longer in my closet than half-decomposing in a landfill. Stick with natural fabrics like silk, cotton, leather and wool. They last longer and are generally more comfortable.”


On Sizing To Keep In Mind (Vintage Sizing And Silhouettes Can Run Differently Than Contemporary Brands)

“Having a tailor you like is helpful! Mine is Ramon on Forsyth St [NYC]! Oftentimes it’s sizing that ends up making a vintage piece not quite work. A tailor can help make it look custom fit. But don’t buy it if you know it’s going to be too small. Easier to make something that is too big fit.


On Tailoring

“Know which parts of your body you prefer (we all have them) and accentuate those because you’ll be more likely to wear the piece if you feel confident in it. If it’s your waist, bring the waist in. If it’s your legs, make sure your pants are the right width and length. A good tailor knows how to help you achieve your desired result.”


On Finding A Versatile Piece

“Can you imagine the ways you’ll wear it with other pieces in your wardrobe? Is it an occasional piece or a wardrobe staple? Have intentions for the pieces you buy and you’ll love them more for their value add.”


Anna’s Favorite Brands

“I like the silhouette of vintage Van Eli and Donald J Pliner shoes. Vintage Liz Claiborne Sport and Ann Taylor have the best silk button downs in great colors and patterns. Pleats Please, JPG, Laura Ashley, YSL… All great.” 


Shopping For Vintage Online

“Find platforms (like The RealReal and Object Limited of course!) and vendors with aesthetics that inspire you and give them a follow. If you continually like pieces on resale platforms the algorithm will catch on and start showing you what you like. 🙂 Use creepy data monitoring to your advantage!”


On Styling Vintage To Look Modern And Fresh

“A quick tip is: if it’s a top or jacket, pair with jeans. Denim makes everything casual and modern. A more involved tip is: don’t wear it with other pieces from the same decade, try to bring it into a more contemporary light with accessories and think about what a “modern silhouette” looks like to you. What are your favorite runway shows? Pay attention to their styling and see how you can mimic in your own wardrobe with belts, earrings, shoes, etc.” 


Trends She’s Trying

“I really am a sucker for a silk button down with shoulder pads. I want to look like a linebacker.”


On Styling Dresses

“Open front dresses are fun and versatile. Wear them as trenches or vests over pants or over other dresses. 


What’s Your Favorite Way To Shop The RealReal?

“I usually start with a favorite brand (Manolo, Dries Van Noten, Margiela) and go from there. The sizing filter is very helpful. There are a few special pieces that I always have an eye out for like Tabi boots so I always click ‘add me to the waitlist’ so I can be notified when they’re available.” 


What Is Your Most Prized RealReal Find?

“My ballet flat collection! I love Repetto and Manolo flats so I’m always looking for those in fun colors. I also just received these amazing YSL low boots in black leather with a suede heel. They’re quite Victorian looking with little lace-up fronts.”



“The JPG cage jacket is iconic, truly. The reimagining of the corset is always a fun exercise (from Westwood to McQueen) but I like how wearable this piece is. It’s a denim jacket but better. To go full Gautlier it should be paired with a very tight pencil skirt but that’s not really my vibe so I chose a silk leopard maxi dress as a base in one look and a midi skirt and tank for another.”



“I love old YSL. The shapes and attitude are strong and confident. The Rive Gauche jacket I picked out is a funny mix of powerful, granny and psychedelic. I love clothes because they tell a story about their wearer without words and this jacket says a lot, a lot. Dressing this one down is the most relatable option (jeans and tee) but it would also look so cute with a slip dress or  bright complementary color silk slacks.”



“Open front dresses are fun and versatile. Wear them as trenches or vests over pants or over other dresses. The DVF wrap dress is essentially what catapulted Diane into the stratosphere of iconic designers (though she didn’t invent them she did make them very popular!). As with most trends, it’s in the part of the cycle where it’s associated with – how do I put this – not-so-cool dressing? I’m sure it will have a resurgence (as most pieces do) but to wear it now, I wanted to give it life beyond the way it’s “supposed” to be worn. Et voila: it’s a jacket!”

Honoring heritage brands and extending the lifecycle of luxury items.