Fashion trends come and go, but some pieces have a way of sticking around—whether it’s because of their comfort, their nostalgic charm, or their undeniable practicality. As we navigate 2025, I find myself reaching for certain so-called “outdated” pieces over and over again. Who cares if the trend cycle has moved on? These items have earned a permanent spot in my wardrobe, and I wear them with pride.
From Ugg boots to the Alexander McQueen skull scarf, these fashion staples refuse to fade into obscurity. And honestly? I’m grateful. Below, I’m sharing my absolute favorite “outdated” pieces that I—and many others—still love.
1. Ugg Boots: The Ultimate Comfort Shoe
💰 Price: $150 – $160
🛍 Where to Buy: Saks Fifth Avenue, Nordstrom, Ugg.com
I resisted the Ugg phenomenon for so long. Decades, even. But when I finally slipped my feet into a pair of Classic Ultra Mini boots, I understood immediately: these are not just shoes. They are an experience. The plush sheepskin lining hugs your feet in warmth during the winter, yet somehow, they also stay cool in warmer weather.
They’ve been deemed unfashionable by many, but let’s be real: comfort is always in style. Celebrities from Gigi Hadid to Kendall Jenner have been spotted in Uggs, proving that they remain a favorite for off-duty style. Whether paired with leggings and an oversized sweater or even styled with a structured coat, Uggs work.
Pro tip: If you’re looking for a slight lift, the Ultra Mini Platform Uggs ($160) give you an extra boost while maintaining that cozy feel.
2. Alexander McQueen Skull Scarf: The Rockstar Edge
💰 Price: $390 – $395
🛍 Where to Buy: Neiman Marcus, Saks Fifth Avenue
I first fell in love with the Alexander McQueen skull scarf in 2011 after visiting the “Savage Beauty” exhibition at The Met. I remember thinking, “This scarf is perfect for adding a little grunge to an otherwise basic outfit.” And I still believe that today.
McQueen’s iconic skull print may have reached peak popularity in the late 2000s, worn by every It-girl from Lindsay Lohan to Mary-Kate Olsen. But thanks to Timothée Chalamet recently rocking it again, it’s officially back in the limelight.
It’s made of silk chiffon, making it lightweight yet luxurious. It looks incredible when draped loosely over a leather jacket or tied onto a handbag for an effortlessly cool touch.
3. Skinny Jeans: The Denim Classic That Won’t Die
💰 Price: $268 – $950
🛍 Where to Buy: Frame, Dior, Nordstrom, Saks Fifth Avenue
For years, people have been declaring that skinny jeans are “over.” And yet, here they are, still hanging in my closet. And yes—I still wear them.
I recently rediscovered a pair of Hedi Slimane for Dior Homme skinny jeans ($950) from the early 2000s, and it hit me: when styled correctly, they can still look incredibly fresh. I love pairing them with oversized blazers or chunky sweaters to balance the silhouette.
If you’re hesitant about full-on skinnies, Frame’s Le High Skinny Jeans ($268) offer a more modern take—fitted, but with a touch of stretch for comfort.
4. Proenza Schouler PS1 Bag: The It-Bag That’s Still IT
💰 Price: $2,190 – $2,290
🛍 Where to Buy: Net-a-Porter, Proenza Schouler, The RealReal
Once upon a time, the Proenza Schouler PS1 bag was THE bag to have. I remember walking into Opening Ceremony and staring at them longingly, unable to afford one at the time. Years later, I finally got my hands on one via The RealReal, and let me tell you—it was worth the wait.
This bag is practical, chic, and holds EVERYTHING. With its slouchy, effortless structure, it feels less fussy than other designer bags. I still get compliments every time I wear it.
If you’re on the hunt, check resale sites like The RealReal or Vestiaire Collective—you can often find one in excellent condition for a fraction of the original price.
5. Crocs: The Ugly Shoe We Can’t Quit
💰 Price: $50 – $250
🛍 Where to Buy: Nordstrom, Crocs.com, Bergdorf Goodman
I know, I know—Crocs are polarizing. But if you think about it, they were never really in style to begin with… which means they can never truly go out of style!
I personally love my Simone Rocha x Crocs Stomp Clogs ($250) for their bizarre yet glamorous aesthetic. But I also own a classic pair of white Crocs ($50) for running errands or walking the dog. They’re comfortable, lightweight, and oddly charming in their own way.
6. Low-Rise Jeans: A Love Letter to the 2000s
💰 Price: $100 – $1,480
🛍 Where to Buy: Massimo Dutti, Khaite, Nordstrom
After years of high-waisted everything, I realized something: low-rise jeans actually suit my body shape better. There’s something incredibly freeing about wearing pants that don’t require constant adjusting.
For a relaxed yet polished look, Massimo Dutti’s Straight-Leg Low-Rise Jeans ($100) are a great everyday option. If you’re ready to fully commit, Khaite’s Lenton Pants ($1,480) offer a luxurious, tailored take on the trend.
7. Common Projects Sneakers: The Minimalist’s Dream
💰 Price: $482 – $530
🛍 Where to Buy: Mr Porter, Saks Fifth Avenue
While chunky sneakers have had their moment, there’s something timeless about a clean, minimalist white sneaker. Common Projects’ BBall Leather Sneakers ($530) are still my go-to.
The sleek silhouette, Italian leather, and signature gold serial number on the heel make these sneakers effortlessly stylish. Pair them with jeans, dresses, or even a suit—there’s truly nothing they don’t work with.
8. Canada Goose Parka: Function Over Fashion (But Still Fashionable)
💰 Price: $1,350 – $1,525
🛍 Where to Buy: Bergdorf Goodman, Saks Fifth Avenue
There’s a reason why I refuse to part with my Canada Goose parka. It has kept me warm through brutal Boston winters and freezing New York commutes. Yes, some might say it’s bulky, but I say: warmth > aesthetics.
If you’re looking for a more modern take, the Aurora Parka ($1,350) offers a sleek design without compromising warmth.
9. 3.1 Phillip Lim Pashli Bag: The Work Bag That Won’t Quit
💰 Price: $695 – $895
🛍 Where to Buy: 3.1 Phillip Lim, Farfetch
Some bags are meant to last forever, and my 3.1 Phillip Lim Pashli bag is proof of that. Nearly a decade later, it still looks as chic as ever, making it my perfect everyday work bag.
Where to Shop for Fashion in 2025
If you’re looking to grab these pieces (or any other fashion staples), here are my go-to sites:
🔹 Net-a-Porter – For designer finds
🔹 The RealReal – Great for secondhand luxury
🔹 Nordstrom – A mix of high-end and everyday fashion
🔹 Farfetch – For international brands
At the end of the day, trends are fun, but personal style is forever. Wear what makes you happy—whether it’s “in” or not.
