Perhaps It's Time to Redefine Classic Style

Insiders discuss what makes something truly timeless.

Photographed by Molly Dickinson
Taylor Tomasi Hill classic style definition

The current state of the fashion industry presents everyone with some rude awakenings. Perhaps it’s that you’re buying too much, you’re not sure where your clothing is sourced or at whose expense, and you could do a lot more to help extend the life of your closet. Maybe all of the above. Conscious consumption is the answer, and often hand-in-hand is the advice to invest in classic wardrobe items instead of ones that are fleeting or quickly disposable. It’s an idea that suggests some style sensibilities simply won’t stick around if they don’t meet certain parameters, but it’s not quite as simple as choosing a neutral-colored tee over something covered in neon sequins.

Classic style can stand the test of time, but the makings are often as unique as each person you’d ask to define it. Among a sample of seven fashion insiders — designers, stylists, content creators, and more — are seven perspectives on what actually constitutes classic and timeless fashion. The findings challenge the idea that obvious basics — trench coats and white tees — make the cut (although, for some, they sure do!) and help redefine “classic” as any piece of clothing that speaks to your truest sense of personal style.

The idea is that something that genuinely makes you feel like your most confident self will likely be the thing you invest more in, take better care of, and wear more often. And with this in mind, the interviews below speak to specific items that qualify as a classic for this group of creative dressers and, ultimately — with some advice-inspired shopping suggestions — may help others refine their own definition of the elusive term.

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Classic Wardrobe Items: Amanda Murray

Amanda Murray’s looks are known to stop you in the middle of your Instagram scroll so that you can take a proper moment of appreciation for her incredible Christopher John Rogers sleeves or her ability to wear oversized coats while never looking like the clothes are wearing her. Her classic style icons naturally include a roster of powerful women. “Bianca Jagger, Diane Keaton, Sheikha Mozah, Diana Ross, Grace Jones, Chloë Sevigny all come to mind,” says the personal stylist and brand consultant.

For Murray, the top essentials come down to accessories and singular showpiece items that can direct an entire outfit. “Great coats — that’s where most of my money goes and it needs to be the investment piece in your wardrobe — sunglasses and shoes,” she lists. “You can never go wrong with any of those items; they’re all statement pieces in their own respective right. When I get dressed, I immediately think of which sunglasses, coat, and shoes I'm going to wear, that's how I build my look.”

Murray says her style today encompasses so much of her past, as well. “I have very vivid memories of begging my mom to buy me tie-dye dresses at a really young age,” she says. “Use of color and layering has always been inextricably intertwined into my personal style. In retrospect there aren't any veins of my style that haven't stayed with me, everything is still very much me, the looks are just elevated now.”

She encourages those still establishing their personal style to stick to the inspiration they love but not to get caught up in the noise of social media. “It’s OK to get cues from magazines and celebrities but never forget who you are, try not to lose yourself in the wave of the algorithm of social media ‘style,’ where everyone looks the same. Your style should not feel forced, it should be the offspring of a symbiotic relationship between clothes and yourself. Wear clothes that make you feel good about yourself, clothes that boost your mood, clothes that make a statement on your behalf without you having to say anything. You’ll know what makes you feel good and what doesn’t.”

Classic Wardrobe Items: Taylor Tomasi Hill

Photographed by Molly Dickson

Taylor Tomasi Hill's approach to classic style elicits much joy. “Style is about what makes you feel most like the best version of you! Once you find that, well then hold on. That’s your classic style,” she says simply. The creative and fashion director of shopping app The Yes has been a street style favorite throughout her career in publishing and retail and is known for her style that has a bit of a wink. “Experimenting is the most fun part about getting dressed! When I challenge myself to create a more classic look,” she says, referring to minimalist icons including Emmanuelle Alt, Gwyneth Paltrow, Carolyn Bessette Kennedy, and Alexandra Golovanoff, “it always becomes a struggle and I end up adding one element of ‘playful’ in the end.”

Tomasi Hill may sometimes gravitate toward the not-so-traditionally classic pieces, but it's an approach that serves her well. “When I worked at W magazine, I had just gotten out of art school and anything ‘extra’ went to my student loans,” she says. “Basically, I was shopping at the Salvation Army in Brooklyn and cool little vintage spots that didn’t mark up (the bygone era). I was always drawn to the prints and oversize silhouettes on the racks as I could mix them or cut them to make a new silhouette that felt more modern.” Today Tomasi Hill’s continuing to find new ways to wear treasures from the past. “I still have the dress I wore to my first day of work at W. At the time it was a ‘60s floor-length schmatta and over the years it became shorter and shorter as my style changed. I still have this electric blue dress that I wear when I need good luck.”

Photographed by Mei Tao

It’s no wonder that when asked about her own classic pieces, Tomasi Hill doesn’t shy away from being bold. “I invested in an army green Junya Watanabe tulle skirt over a decade ago. It’s probably my most coveted ‘timeless’ thing in my closet as it still represents me best: tailored and quiet in the front, playful party in the back.” Other classics include heavier soled brogues and creepers — “a go-to style for me because of the playful, masculine aesthetic” — and menswear button-downs — “I style them with literally everything: paired back to shorts, on their own, under corsets, wrapped around my waist…” She also lives in the brand Kule, she says, which is known for its endless options of striped designs. “They’re classics in my wardrobe and it’s rare if I’m not wearing at least one piece — more likely there are several that I’ve layered,” she adds.

Classic Wardrobe Items: Norma Kamali

Photographed by Mark O'Flaherty

“My first recognition of why timeless and classic were going to be important to me as a designer came very early when I was 15 or 16,” shares Norma Kamali, whose eponymous brand launched well over 50 years ago. Kamali discovered vintage stores at that point in her teens in the ‘50s and recognized its long-term appeal. “I was obsessed with classic films so I wanted to dress like that. Evening gowns during the day, I didn’t care. I was very different from everyone wearing those clothes but I felt great in them.” By the ‘70s Kamali started making clothing. “I decided that I wanted to create vintage of the future which would mean classic style, because if I was wearing vintage clothes designed and created 30 to 40 years earlier, that in itself defines those clothing as timeless and classic. It didn’t mean they looked a certain way or had to be a certain type of clothes, it’s that the essence of that piece of clothing would be that it could survive time.”

An enduring essence certainly applies to the Norma Kamali brand that’s behind several iconic styles that remain important today, including the signature Sleeping Bag Coat or swimwear designs that still can be found on magazine covers today. “In the ‘70s I created these jersey dresses and they’re still in my collection. Why? Because they don’t define a trend and they have their own characteristics,” she adds of the brand’s All-In-One dress. “It’s just a tunic but you can wear it in all the ways you can imagine: strapless, one-shoulder, off-shoulder, a skirt. It’s jersey, it’s washable, it’s easy and everyone looks different in it. It would not define the person, the person would create it in a way that would define themselves in this look.”

This ease and versatility is naturally not only indicative of the brand’s approach to classics, but Kamali’s as well, who counts the All-In-One as a personal classic piece. Others include the Sleeping Bag Coat — “I still make and wear them every year because I hate the cold.” — and sweats — “Workout clothes have been a part of my wardrobe as well since the ‘80s.” This addition speaks directly to her active lifestyle and investment in wellbeing, something that’s documented in her recently released book Norma Kamali: I Am Invincible, but she also points out that they can be worn with sneakers and heels alike. “At 75 and doing this for over 50 years, it’s much easier for me now to say I know that that’s classic. I know that that’s not going to survive,” she says, referring to her collection, as well as her personal wardrobe.

Classic Wardrobe Items: Lauren Chan

“The most classic garments, in my opinion, are a blazer, a trench coat, and in a post-2020 world, a knit set,” says model and founder of plus-size label Henning, Lauren Chan. “At Henning — shameless plug — we make all of those things,” she adds. Chan, also a model and former editor, says that she considered her style to be classic in some of the most common ways you may hear the term. “The phrase ‘classic style’ makes me think of neutral colors and simple silhouettes; it makes me think of wardrobe building blocks that all go well together. My personal style is fairly classic — I find it to be the most comfortable, chicest, and honestly, easiest way to get dressed.”

Chan says she draws a lot of inspiration from traditional menswear style — “while I don’t frequent a little black dress, I probably own 20 blazers” — and finds there’s endless versatility in the aforementioned pieces that are essential to her wardrobe. “Even if your style isn’t ‘classic,’ you can fold those elements of timeless style into your look. If you love patterned dresses, top ‘em off with a blazer. Into bright sweatsuits? Add a blazer when you step out for an errand. You get the gist.”

In addition to specific items she returns to often, Chan says that the classic ones in her wardrobe are worth the investment for high-quality options. For her, that means the stretch-wool, double-breasted style of Henning’s Bank Blazer or a cashmere fabric of the brand’s latest set offerings. “It’s better for your wallet and the planet to purchase a very well-made garment upfront than to replace it in a season or two because it pills, thins, or rips,” she says. “Also, because you’ll be able to throw on your classic pieces with everything and likely wear them on repeat, the up-front investment will make you look ever-elevated, even if the rest of your look is made up of more affordable pieces.”

Classic Wardrobe Items: Anna Z Gray

"‘Classic’ evokes people who know the rules well enough to break them,” says Anna Z Gray, co-founder of Object Limited. “The best observers and amateur social anthropologists make for the best interpreters of style, right? Deeda Blair, Grace Jones, Tina Chow, David Bowie. They have personalities that are enhanced, not manipulated by the clothes on their bodies.” The model and vintage expert, like the aforementioned personalities, is no stranger to trying different looks and seeing what sticks. It’s brought her to a better understanding of herself.

“I've had a lot of phases: preppy, alternative, full sequin, elegant... All those eras culminated in an understanding of what I like to wear and why. I'll try anything once but now I know what I actually like,” she explains. Unsurprisingly, it’s vintage pieces that round out her most important staples. “Some of those items include my favorite Student Fit Levi's, a silk black-and-white checkered print button-down, a Michael Kors-era Celine monogram print pony hair bag, pale yellow snakeskin Ferragamo mules, and a vintage navy leather Loewe chore jacket that I found in Madrid.”

Gray says that classics, whatever they may be, should be well-made, versatile, and able to be dressed down or up for multiple occasions. Finding them may require trial and error, but it’s a ride worth enjoying. “Dress like people you admire until you can determine what shapes, materials, silhouettes you find yourself returning to. The best outfits are the ones you feel good in because, as mentioned earlier, you should wear the clothes not vice versa.”

Classic Wardrobe Items: Nawal Sari

For digital creator Nawal Sari, the definition of classic style comes down to how each piece can be worn and transformed. “When I started my journey in fashion I learned that if I had the classic staples, I could add accessories however I like to be ‘edgy’ and unique,” says the Sydney-based Sari. “I could find a photo of my mum from the ’90s with the same silhouette but with her own twist and I love that.”

As a TikTok creator with a massive community following, Sari says social media does play a role in how she’s crafted her point of view. “There are so many new trends surfacing and I'm constantly consuming so much content that I'm always onto the next thing. Last week there were Penny Lane coats and now I'm on the hunt for crochet pieces and fingerless gloves. Social media allows you to experiment and almost be yourself more comfortably than you would in the real world. I feel more comfortable wearing a lot of my wardrobe pieces online because people accept creativity a lot better than in person.” That said, Sari does stand by several pieces deemed classic to her closet.

“I love wearing my hijab in fun ways and one of them that is super unique to me is styling it as a bandana,” says Sari, who counts satin scarves and bandanas as classics. “It’s fun and very on-trend with the Y2K/90s rise that's happening.” Sari also lives by puffed or balloon sleeves that she layers with cropped or corset tops — “I don't wear alone for modest reasons” — as well as turtlenecks that allow her endless styling possibilities to explore.

Classic Wardrobe Items: Kelly Augustine

Stylist and influencer Kelly Augustine has been documenting and sharing her personal style and its evolution for around a decade and shares that some phases have remained important, others less so. “Motorcycle jackets have always been in heavy rotation in my closet, I’ve built a nice collection of them over the years,” she says. “Tutus didn’t make it past the early 2010s!”

Today, with her styling career taking off and a reality TV show in the works, Augustine has cemented the classics in her closet as “timeless staples that go from year to year.” More specifically that means, “turtlenecks (in different weights and lengths for the seasons), perfect-fitting denim, and glasses. You can’t go wrong with those.” While these building blocks are accessible and straight-forward, they also offer tons of opportunities to get creative as so many of her past ensembles have shown, be it with gorgeous full-length robe coats, tailored leather separates, or tons of printed dresses, pants, and skirts you can often spot on her Instagram feed.

“I always advise my clients to think about things they automatically reach for, and to think about parts of their body they are super comfortable with,” she advises for those shaping their own classic definition. “That will help choose the pieces that they will want to wear every day!”