5 Timeless Fashion Trends That Never Go Out of Style

Stylist and fashion editor Natalie Cantell taking a mirror selfie wearing Stella McCartney denim, a white flowy summer top, and a black Celine Croque shoulder bag.

I know, I know—”timeless trends” reads like an oxymoron, but the point I’m here to make is that having classic style isn’t mutually exclusive with being on-trend. Yes, the trend pendulum swings back and forth, putting certain cool things on my radar each season. After 15 years in the fashion industry, I don’t overhaul my style for trends. Shopping tends to be more about refreshing and evolving the mainstays in my wardrobe—the things I I feel good in and are practical enough to work in real life.

Take denim, for example. Wide-leg jeans often get pegged as a trend even though they’re shoppable every season, putting them firmly in the “timeless trend” sweet spot. I know by now that this silhouette is my happy place. Specifically, I like a fit that feels almost like trousers and a length that just meets the ground when I’m wearing flats. Even within that criteria, there’s still loads of room to play with washes and details that feel fresh and forward, and this all applies to the other timeless fashion items that have become anchors in my wardrobe. Here are five of those classic staples I’m perpetually shopping and the trending takes on them to shop this season.

Timeless, On-Trend Denim

Since we’ve already touched on my commitment to trouser-like denim styles, let’s take a moment for the details within the trend that I’m into at the moment. I really am in love with this Stella McCartney pair. The corduroy feels like a great fall twist, and the blue on blue means they still read as classic jeans that aren’t doing too much. I’m also particularly into cream denim for fall—it seems like more of a summer staple but does such good things to freshen up easy cold-weather looks.

Stella McCartney

Denim & Corduroy Wide Leg Pants

Mango

Devin Wideleg Jeans With Frayed Hem

ASOS Curve

Easy Straight Leg Jeans in Light Blue

AGOLDE

Dame High-Rise Wide-Leg Jeans

Toteme

Pleated High-Rise Wide-Leg Organic Jeans

Good American

Good ’90s Carpenter Jeans

Timeless, On-Trend Handbags

On one hand, simple black shoulder bags with minimal branding are peak anti-trend. They’re absolutely timeless, making them perfect investment pieces, yet they’ve definitely been on an upswing in terms of popularity this year. I love my under-the-radar Celine Croque bag (it’s currently sold out in black—sorry!) for being extremely low-key and as slim as I can get without sacrificing any of the things I realistically need to have with me. I’m into styles that fit my phone without doing any gymnastics along with lip balm, sunglasses, and a small cardholder if I’m going somewhere where I need a physical card to pay. (KazuNori, I’m looking at you.)

Madewell

The Sculptural-Buckle Shoulder Bag

KHAITE

Lina Medium Suede Shoulder Bag

Reformation

Medium Rosetta Shoulder Bag

Longchamp

Roseau Essential Half Moon Hobo Bag

Timeless, On-Trend Sandals

They may be a key footwear trend this summer, but flip-flops are timeless as far most of the southern hemisphere is concerned. As a New Zealander who used to live in Australia, I’ve been on the flip-flop train my entire life, so a warm welcome to all that are new here! I have two pairs of high-rotation brown flip-flops—Havaianas for everyday jaunts and a square-toe Toteme pair for when I’m feeling a little fancier. They’re a perfect way to overlap trends, such as jelly footwear like those from Ancient Greek Sandals and The Row and those enduring pops of red that just keep on feeling relevant.

MANGO

Leather Sandals With Adornment

Toteme

Flat Croc-Effect Leather Flip Flops

Havaianas

Slim Square Flip Flop

TKEES

The Boyfriend Flip Flop

Ancient Greek Sandals

Saionara Jelly

A.EMERY

Morgan Suede Flip Flops

Timeless, On-Trend Trench Coats

Fall is coming, so let’s talk layers. Like most of you, I’ve had some iteration of a trench in my closet my entire adult life and have cycled through every tweak imaginable. Contrast linings, tie belts, shoulder pads… You name it. The last five years or so, I’ve landed on oversize, relaxed styles that work as well undone as they do buttoned. If this is your vibe as well, don’t skip the menswear section, or you’ll be missing out.

H&M

Shoulder-Pad Trench Coat

MANGO

Cotton Trench Coat With Shirt Collar

L’Academie By Marianna

Ayisa Trench Coat

Lovers and Friends X Maggie Macdonald

Leah Trench Coat

Favorite Daughter

The Charles Tie Waist Double Breasted Trench Coat

Timeless, On-Trend Eyewear

If you’re convinced that 99% of sunglasses don’t suit you (hello, it’s me), then eyewear is maybe the strongest argument there is for committing to a style you feel works. Aviators are just about as classic as it gets. If the oversize shape works for you, the trend for the past few seasons has been leaning away from metal-framed Top Gun styles and toward acetate pilot frames with tinted lenses.