I have determined that there are two levels of vintage style expertise: Level one is the ability to identify true gems, i.e. the perfect silk, lace-trimmed nightgown hidden underneath a pile of polyester dresses, or a wispy polka-dot YSL blouse strewn next to a stack of torn graphic T-shirts. Level two is the ability to take said gems and style them on yourself in a way that looks distinctly fresh and modern.

Since I’ve barely mastered level one, level two feels like a near-impossible feat (and the instances in which I’ve worn a compilation of vintage finds only to end up looking like an awkward sepia photograph of my grandmother in the early twentieth century don’t necessarily bolster my confidence). And yet, I know it is possible, because I see people accomplishing it all the time.

Anna Gray is a shining example. You may recognize her from this week of outfits, or this treatise on the Met Gala’s “Heavenly Bodies” theme, or from @object.limited’s Instagram. As the creative director and co-founder of Object Limitedan e-commerce platform that specializes in high-quality vintage goods, Anna is well-versed in the art of identifying true gems. As the person who routinely styles said gems on herself to promote Object Limited’s pop-up vintage bazaars, or the offerings on its app, she is also well-versed in the art of showcasing how to create modern looks with pieces from the past. 

Eager to absorb some of her knowledge like the sink sponge that I am, I asked her to share her best tips for shopping vintage and enjoying it accordingly. Scroll down to read her advice, along with a visual demonstration by way of seriously good outfits.

Tip #1: Go Outside Your Comfort Zone

Moschino jacket via @drakeburnette, crochet dress via @foundby, mules via @object.limited, silk scarf via @gillianzinser worn as belt

“My most treasured vintage finds are always the result of going to weird places and making friends with the store staff,” Anna told me. “I have found Pucci dresses in Goodwills and Hermes bags at tiny shops in the middle of nowhere.” She recommends grabbing a couple friends (who either have thrifting stamina or a good book to read), and going to Queens or New Jersey or wherever you can get with whatever mode of transport you have. And be nice to the sales people always! They know where the good stuff is hiding.

Tip #2: Prioritize Quality Materials

White vest and black pants via @o.laroche, shoes and belt via @object.limited, blazer via @charlottefrancesvintage

If you’re vintage shopping with limited time, or aren’t sure where to start and aren’t looking for something specific, Anna advises avoiding synthetic materials and honing in on long-lasting quality. Big thrift stores are the least curated in terms of aesthetic but are very well organized by category. In the outerwear section, look for real leather, shearling, trench coats, or high-quality nylon puffers. In the dress/blouse/sweater sections, look for 100% silks, cottons, wool, cashmere. In pants, look for raw denim. These starting points will help narrow the options into one digestible pile.

“The cream DKNY vest I’m wearing in this outfit is 100% silk, which is what makes it look expensive,” Anna said. “The linen/cotton blazer with abalone buttons is a nice layering piece with the option of pseudo-oriental collar or, when folded, small lapels.”

Tip #3: Mix Up Your Decades

Cami and nylon skirt via @o.laroche, shoes via @object.limited, bag via @leandramcohen

“Mixing decades is a good way to avoid looking like you’re wearing a costume,” Anna said. “Unless that’s your thing! Then wear that poodle skirt with that short sleeve cardigan, you cutie.”

As an example, she noted that wearing period vintage (i.e. an Edwardian blouse) with contemporary clothing (like sneakers or jeans) makes everything look a little more modern. Layering unexpected items, like a halter over a button-down, can also help refresh an otherwise dated look.

White tuxedo shirt via @o.laroche, red halter via @charlottefrancesvintage, star pants via @foundby, shoes via @object.limited

Tip #4: Negotiate, Baby!

Green suit via @foundby, military woven shirt via @shopnarro, Paloma Picasso bag via @object.limited, woven slides via @facewithaviewvintage

The prospect of haggling can be intimidating, or even guilt-inducing, but it’s actually part of the game and expected when it comes to vintage shopping. “Vendors often mark items up at least 50% and they’ll rarely sell to you for less than they bought an item for,” Anna told me. “Once you have a ‘yes’ pile, tally up all of the prices and ask yourself what you would reasonably like to pay for the total. Calculate what 15-20% less than that is, and (while being very firm but friendly!) ask if you can pay that in total. Then you have 15 to 20% wiggle room to climb to the amount you’d ideally like to pay.” She also recommends mentally prioritizing your items so you’re willing to let go of certain pieces if they don’t budge.

Any vintage shopping and/or styling tips you’d like to add? Have at it in the comments.

Photos by Emily MalanStyling assistance by Maggie Lanham. 

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