I was wading through my outfit inspo folder looking for a pic buried deep in 2021 when I noticed an intriguing theme: even when I was heavily into maximalist dressing, most of my outfit saves fell into the so-called timeless dressing category. And I couldn’t help but wonder1, what makes an outfit timeless or trendy? Since I’m in a constant state of trying to buy fashion with longevity, I had to know more and pulled five saved looks from the last five years to investigate.

Quick note: while I’m not into flash in the pan microtrends or letting trends dictate how you shop and get dressed, being trendy is not a bad thing. A world without trends would be boring and flat. Trends keep the fashion industry moving, they heighten our creative energy, and the stellar ones become iconic pieces that you can wear year after year.

2021: The Matching Skirt Set

Scrolling back through

What’s Timeless: This skirt set is contemporary enough to wear today with its clean lines, elongated sleeves, and subtle ribbing, but still timeless enough to wear into 2030. While butter yellow is the color of 2025, soft yellows will remain relevant going forward, unlike the neon brights that dominated 2021.

What’s Trendy: The sandals are on the trendy side with their embellishments and strap placement, but the minimalist design keeps them from looking too OTT.

The Verdict: Timeless

2022: The Statement Crop Top

I found Prudence Richardson’s Instagram right around the time she began focusing on minimalist dressing, and found myself saving her statement minimalist outfits, like this bubble skirt, this sheer top/skort combo, and this lace catsuit (more as living vicariously through than wearing myself). Looking back, her style might have planted the seeds for my sheer skirt obsession.

What’s Timeless: Dark wash denim with a subtle flare leg and black square toe boots will always be in style. What makes these items especially versatile is that they can anchor a big statement piece (à la the below Frame top) or be paired back to a western denim shirt or preppy cable knit sweater - it’s all up to you how to style it.

What’s Trendy: There’s no doubt that this was the top of the moment in 2022 during peak revenge dressing: you couldn’t help but feel the going out energy radiating from every fiber of its cropped length, extreme ruching, and supersized balloon sleeves. While this lives in the trend camp, the white color and structured shape bring a hint of minimalism, which means this top can be brought out again and again to be restyled with whatever you’re feeling in that era.

The Verdict: Trendy

2023: The All Black Outfit

I love Grece Ghanem’s main aesthetic POV: maximalism with bright colors, bold prints, and fashion-forward pieces. She occasionally throws in the perfect minimalist look that immediately makes it to my outfit inspo folder, and this all-black ensemble is one of her very best (this one, too).

What’s Timeless: This is a true “timeless with a twist” outfit: the tonal black color palette, midi skirt, and slouchy turtleneck can still be worn a decade from now, while the skirt’s zipper detailing and bag’s bubbled weave make it visually interesting. The bold earrings and subtle cat eye sunglasses make this err on the right side of timeless.

What’s Trendy: These Celine sandals circa 2015 are on the trendy side with massive gold buckles, thick straps, and platform soles. But even at 10 years old, they still work as a trend-forward statement shoe in 2025, and they’ll keep working in 2035. Old Celine Phoebe Philo never misses.

The Verdict: Timeless

2024: The 90s Redux

Denise Nørgaard is hands down one of my top style inspirations and her styling super power is dramatic silhouettes, from peplums to pencil skirts to maxi coats. She makes everything look timeless and of-the-moment all at once, like this leather jacket and slip skirt homage to 90s minimalist dressing.

What’s Timeless: The slightly oversized deep brown leather jacket is a classic, with slouchy sleeves and a minimal hardware. Paired back to a lighter brown t-shirt and a black maxi skirt, this is an outfit that you can revisit every fall for the next five years.

What’s Trendy: Denise uses trendy accessories to bring a modern edge to her outfits. Case in point: shiny thong sandals and a jumbo raffia bag give 2025 vibes to her leather jacket and black maxi. Both add strong textural elements between the matte weave and high shine finish. Will either of these be considered truly timeless in 10 years? Probably not, but they might be the nostalgic pieces from the time we wore flip flops with everything and carried massive bags everywhere.

The Verdict: Timeless

2025: The Big Blazer + Sheer Skirt

I had to revisit this look from Div Ravindran because it’s the outfit defining how I want to get dressed in 2025. The simple styling is taken up a notch with subtle use of color, proportion play of oversized vs. streamlined, woven fabric against sheer, and masculine/feminine details. Ending with the two-tone Miu Miu loafer slingbacks that are the gold dust on my resale wishlist right now.

What’s Timeless: Like

What’s Trendy: The sheer skirt and pointy shoes are trendy in a way that indicate a specific fashion era, but since they’re understated statement pieces, they can be worn in the future with whatever trend has captured your creative eye.

The Verdict: Both

The Conclusion:

The one thing all the timeless outfits had in common? They used trendy accessories to create a modern feel. And the trendy outfit? It used timeless pieces to tone it down. A great argument for buying items with longevity in mind and zhuzing them up with fun accessories. Or a going out top that might not stand the test of time every single season, but can be pulled out over the years to make a statement.

Fashion Notes:

We launched a new series on

THIS is my Roman empire.

I live for a great close-up shot and these from

Ganni debuting built-in shoe charms on their iconic Buckle Ballerina2:

Nosy merchant question of the week:

That’s it for this week, thanks for reading! I’d love to know what makes something timeless or trendy to you? Are there things in your wardrobe that you think you’ll still be wearing 10 years from now? Is there anything you’re ready to part with because it feels too early to mid 2020s?

Leave a comment

If you like what you’ve read, please consider tapping the ❤️, commenting, or sharing. It really helps create more visibility as a free newsletter. Thank you :)