How to be nostalgic without looking retro

For the past few seasons there’s been one prevailing trend…nostalgia!

Today’s edition of Consider Yourself Cultured is brought to you by The RealReal.

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Since we emerged from lockdown, we’ve been in what feels like a constant loop of trends that all look backward. Some have had real staying power, others less so, but the common thread has been a return to silhouettes that are tied to very specific eras, each with a distinct visual language. And while it almost goes without saying that if you’re shopping purely based on trends your closet will start to feel dated the second the next thing rolls in, the same thing can happen if you lean too heavily into nostalgia, even if it’s for a time you never lived through. At a certain point, it stops feeling like getting dressed and starts feeling like a costume.

The balance is really about knowing when to indulge the reference and when to pull it back, how to let nostalgia guide you without letting it define you entirely, making sure you still come through in the end. Which brings me to today’s partner, The RealReal. I’ve been a longtime user, and what I’ve always appreciated is that it allows for that kind of experimentation while also giving you the tools to build a wardrobe that feels more like you!

Whether it was my brief pandemic-era fixation on a ’50s doyenne silhouette (which I quickly realized wasn’t entirely me, even though I still love the idea of it), or my phase of trying to track down as much Raf Simons-era Calvin Klein as possible (I’m down to one piece now), it’s always been a place where I could figure things out in real time. And when something no longer worked, just as easily let it go and make room for what does.

So to help navigate the push and pull of nostalgia, and to make sure your wardrobe still feels current while actually feeling like you, here are a few ways to strike that balance.

Mix and match the decades

The beauty of shopping somewhere like The RealReal is the access. You’re suddenly within reach of true fashion holy grails, SS 2022 Prada, SS ’97 Comme des Garçons (the “Lumps and Bumps” collection), a Versace dress that’s from the same collection as the 13 Going on 30 dress. The list really does go on. The only catch is that when a piece is that specific, that tied to a moment or a collection, it can start to read like you’re stuck in a bit of a time warp. Even something relatively recent, like that Prada skirt, carries the weight of its moment which was all about this mini skirt revival which by extension was a bit of a callback to the ‘60s. So the challenge becomes how to make it feel like yours. For me, that usually comes down to mixing decades and references until it lands somewhere more personal.

Last weekend I rewatched Catwalk (great soundtrack, by the way), and it got me thinking about those Versace campaigns shot in Miami in the ’80s and ’90s. This is my take on that energy, anchored by just one actual piece from the era—1993, to be exact. Aviators and printed silk Versace shirt from ’93. Levi's denim trucker that was new to me but sourced secondhand, with appliqués I added to the back. Zankov sequin miniskirt from The RealReal that leans a bit mod ’60s in attitude. And wraparound espadrilles that are technically contemporary but carry a faint ’40s sensibility.

Longtime readers know I love a reference. It’s often the starting point when I’m styling a look, but it also guides how I shop. I’ll rewatch a Alfred Hitchcock film or something like American Gigolo, and my first instinct is to run to The RealReal in search of jacket fit for a Hitchcock blonde, or just Armani, Armani, Armani. But as much as I love those references, I also know that if I were to fully commit to let’s say a ’50s dress with decade-correct shoes and coat, it would veer into costume territory, which is probably the worst place to land when getting dressed.

(Top) The other day I was in a store and the sales associate was wearing a Mary McFadden tunic, Pleats Please Issey Miyake pants, and a cardigan that felt close to the classic Agnès B. snap style. This is my take on that mix: a Mary McFadden mutton-sleeve jacket that taps into her way of pulling so-called dated silhouettes into something that felt current in the ’70s and ’80s, paired with an Issey Miyake pant and a strappy Khaite shoe to keep it from slipping too far into nostalgia.(Bottom) This Romeo Gigli jacket from ’91 has a couture-leaning finish that nods to the ’60s. Pairing it with Bermuda shorts and rounded, tinted frames shifts it into something a bit more downtown, less precious.

And there have been plenty of times where I’ve gone hunting for a piece inspired by a film or a runway, found it, tried it on, and it just didn’t feel like me, even after pairing it with more modern pieces. That’s part of it. The upside of shopping somewhere like The RealReal is that there’s less pressure. You’re often getting these vintage or archival pieces at a significant discount, which gives you the freedom to take risks, try things on for size, and move on if they don’t quite stick, without it feeling like a major loss.

Wrong [fill in the blank] theory

A few seasons ago, I wrote about the “wrong jacket theory,” which was really my take on Allison Bornstein’s “wrong shoe theory.” The idea is simple: to create contrast and a bit of intrigue, you choose the piece that doesn’t quite make sense on paper. So instead of finishing a look in the expected way, you go in the opposite direction. An evening-forward coat thrown over something casual, or a flip-flop grounding a more formal dress.

Masion Margiela tuxedo jacket that I snagged from TRR (alt), Versace striped polo, A.Presse cotton sweatshirt (alt), Polo Ralph Lauren khaki pants, RRL embellished leather belt, The Row flip-flops (here’s the platform version of the infamous flip-flop).

Essentially the same look as above with the addition of a vintage French work jacket (in the same vein as this) to give it more of that causal flair, and The Row satin knot heels (here’s the black version of the heels).

In the same way that mixing decades can make something feel new, designers have been refreshing vintage-leaning silhouettes by avoiding the “right” choice altogether. Oxfords with an airy sundress, crystallized slides with capri pants. There’s a willingness to be slightly off, and that’s what makes it work.

(Top) I love the idea of an evening dress, like this one from The Row that looks like liquid gold, paired with something as quotidian as a flip-flop. It grounds the look, pulls it out of that rarified space, and makes it feel, for lack of a better word, human. If you’re going that route, it helps to keep the accessories evening-forward—cascading disc drop earringsand a proper clutch keep the balance intact. (Bottom) I’ve said this before, but when I’m running errands, grabbing a coffee, I’m often in pajamas with a more formal coat thrown on top. In the same way the flip-flop tempers the evening dress, an evening-leaning coat elevates something otherwise casual. Lately, I’ve been reaching for a sweatshirt, which pairs nicely with cargo pants, and then finishing it with a piece of jewelry to bring back a bit of polish.

And I don’t think the “wrong” theory stops at outerwear or footwear. Over the past few months, I’ve been particularly attached to a sweatshirt. When I was in London and Paris, it became something of a security blanket, I wore it everywhere, even in moments that probably called for something more considered. Around the holidays, I kept coming back to the idea of pairing a sweatshirt with a long sequin skirt. It strips away some of the pomp and ceremony and makes the whole thing feel a bit easier, a bit more lived-in.

Disregard the categories of “evening clothes” and “day clothes”

Though I love myself a sweatshirt these days, there’s no denying that I’m just as drawn to the shinier, sparkly pieces in my closet. And because I could never quite get behind the idea that those pieces are reserved for “special occasions” only, I wear sequins during the day just as easily as I’ll throw on a sweatshirt for an evening event. Getting through life feels reason enough to celebrate!!!!

Veronica Beard embellished evening jacket, Me +Em tuxedo shirt, High Sport fringe pants (non fringe pants from the brand here, here, and here), Rene Cavallia crystalized wrap sandals (these are basically the same shoe but with a bit of a block heel), Co embossed clutch (when in doubt Judith Leiber is a great evening bag resource, Don't Let Disco pediorit choker, Jacques Marie Mage tortoise shell sunglasses.

The categorization of clothes feels a bit obsolete. That’s not to say it never served a purpose, but now it feels more like a personal decision what reads as day or evening, rather than something that’s been predetermined for you.

(Top) I love dressing like a lady who lunches as much as the next person, but I get that it’s a fairly specific proposition. There’s something appealing about pairing a tweed jacket (this one from Veronica Beard) with jeans. Not exactly groundbreaking, but when the denim is a bit more directional, like this pair from Y/Project, it pushes the whole thing past the usual jacket-and-jeans formula. To bring it back down to earth, a canvas tote that can double as a work bag keeps it practical. (Bottom) There’s something quite satisfying about a knit twin set paired with something more opulent, like a sequin skirt. I’m particularly drawn to this one because it’s not that typical high-shine gold. It feels a bit weathered, almost bronze depending on the light. To play off of that color a brooch adds a nice finishing touch.

And don’t get me wrong, there have been plenty of times where I’ve bought some truly fantastic evening piece, like an ’80s soufflé-style ball skirt, with every intention of making it more wearable, only for it to fall flat. Thankfully, just as it’s easy to find these pieces at a significant discount, it’s just as easy to consign them with The RealReal. Lately, I’ve actually preferred taking site credit when things sell, it gives me the chance to keep experimenting, and to find the pieces that really do work for me.

Don’t be afraid to shop across the gender line

I think it goes without saying, I’ve never really had an issue with using every crayon in the box. It makes a look more interesting, yes, but more importantly it makes it feel personal.

6397 nylon trench coat, Bode nautical flag short sleeve shirt (not a one for one but just as good), Tory Burch fish scale pailette skirt, Polo Ralph Lauren cable knit socks, Prada criss cross sandals (this is a pretty decent alt).

People often ask how I found my style, or how I got comfortable dressing the way I do, and the truth is that The RealReal was a huge part of that. I went to school in New York and being on my own for the first time, in a city that really gives you full permission to be yourself, I took that as an opportunity to experiment with styles I wasn’t allowed to explore back home in Virginia. Of course, I was a college student, so funds were limited, but because The RealReal had so much at relatively reasonable prices (Exhibit A, Exhibit B, Exhibit C), I felt free to try things out and then, a few months later, consign them as I started to understand what actually felt like me.

(Top) Undercover printed short sleeve shirt, Prada gold metallic skirt, suede Birkenstock sandals. (Bottom) Emporio Armani bomber jacket, Giorgio Armani printed set, Church’s oxfords (though these are technically a woman’s shoe, it still harkens to more so of a menswear silhouette).

In the same way that occasion-based dressing feels a bit obsolete, the idea of gendered clothing does too. It’s less about who something was originally designed for and more about whether it works on you, both physically and stylistically.

Jewelry makes all the difference

Jewelry is extremely personal, and it’s often the thing that makes a look feel like yours. Even if you’re reaching for something that clearly belongs to another era, like a bakelite bracelet or a brooch, if it resonates with who you are, it reads as timeless regardless of where it came from. So when a look starts to feel a bit too of the moment, I tend to turn to accessories to bring it back down to earth.

Lizzie Fortunato Stone, Bead & Pearl Cabana Bead Strand Necklace, Mark Davis 18K Bakeliet & Sapphire Bangle Bracelet, 14K Dyed Pearl Pin Brooch, John Hardy Dot Wrap Bangle Bracelet, Cellino 14k Onyx Dachshund Brooch, 14k Lapis & Turquoise Ring, Tory Burch Enamel Shell Stud Earrings.

That’s all from me, happy shopping on TheRealReal!

XX

JJ

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