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