An Argument for the Return of Classic Dressing

With a new It bag or must-have jean style dropping daily, it can sometimes feel exhausting trying to keep up. If you’re anything like us, you swing between loving trends one day and pining for a timelessly chic aesthetic the next. In the latter moments, we inevitably turn to Ralph Lauren. Synonymous with crisp tailoring and that nostalgic New England sensibility, we love the feeling of (for lack of a better word) put-togetherness that washes over us the second we slip into his refined blazers and crisp button-downs.

"Ralph Lauren is an iconic brand that represents timeless style. It’s more than clothes—it’s a lifestyle,” says blogger Ann Kim. Kim, along with Marta Pozzan and Madelynn Furlong, was invited to the newly renovated Ralph Lauren flagship located on Rodeo Drive to style pieces from the designer’s Icon Collection. Naturally, our very own co-founder Hillary Kerr was among the fashion glitterati. Curious to see what we mean? Today we’re showing you how these four stylish women dress for the classic look.

Furlong, art director at Wide Eyed Legless, has an affinity for monochromatic looks, which really shines through in this Ralph Lauren look. Her advice for following suit? "I found one piece I really loved—the jacket—and based the rest of the outfit around it,” she explains. And since her personal style leans toward the simple side, she made sure to keep the look streamlined and minimal, finishing things off with straight-leg trousers, strappy sandals, and a fun mini handbag.

True to the spirit of classic dressing, Kim, a Los Angeles–based art director and the blogger behind Andy Heart, relies on a daily uniform of sorts to get her through the workweek. "I love the idea of having your go-to pieces, especially for those days when you don’t have time to think about an outfit,” she says. As she demonstrates here, the key to building the perfect uniform is sticking to neutral pieces in classic shapes. Kim also believes in the adage "less is more,” so she opted for a structured camel coat, tailored pants, and black pumps. The result? A highly versatile look that easily transitions from desk to drinks.

For Pozzan, an Italian fashion editor–turned-blogger, the appeal of classic dressing is all in the tailoring, especially where jackets and coats are concerned. "It feels empowering and very iconic,” she says of her favorite menswear-inspired pieces. "It’s not about being old-school; it’s about a specific attitude—a strength and assertiveness.” Here, she adds in some chromatic contrast by pairing her navy-blue blazer with crisp white denim. To pull the look together, she layered in lighter top underneath (perfect if you decide to take the jacket off later in the day).

Think classic dressing leaves feminine pieces out of the mix? Think again. Clique Media Group co-founder Kerr applied her signature feminine, retro aesthetic to her look in the form of a leather pencil skirt, a striped shirt, a safari jacket, and chic black pumps. The resulting outfit is playful and fun (which her co-workers will attest is indicative of her personality) while still being incredibly traditional and well-structured.

Looking for more classic pieces to add to your wardrobe? Head to Ralph Lauren to see and shop spring-ready picks.