I Asked 3 Resale Experts for Luxury Items Worth Investing In—They Said These


A lot goes into making a serious investment, no matter what it is. Just like you wouldn’t purchase a home or a car without proper planning and research, most people wouldn’t drop a significant amount of money on a designer bag, coat, or pair of shoes on a whim either. Knowing whether said item will lose its popularity in a season’s time, its resale value in the short and long term, and more are all variables to consider ahead of any type of financial exchange. Luckily, there are experts for that—and I just so happened to recently catch up with three of them. 

Currently, designer offerings are the priciest they’ve perhaps ever been and the most desirable, making it all the more important for us to do our homework beforehand. Knowing that, I called on Jessica Henderson, a senior curator at FASHIONPHILE; Kelly McSweeney, The RealReal’s senior merchandising manager; and a representative at Vestiaire Collective to teach all prospective investors about the designer items that pack the most punch financially speaking. Ahead, see and shop the items they think will best hold their value down the line.  

“Despite constant shifts in the market, ongoing demand for ultra-luxury handbags, watches, and jewelry prove these items will always make for coveted investment assets. Iconic, timeless pieces that never go out of style such as the Hermès Kelly, Chanel Double Flap, and Louis Vuitton Pochette Metis handbags continue to age like fine wine, with the highest increases in sales YoY. Watches also have a high resale value with brands like Rolex and Patek Philippe in particular holding their value. When purchasing an accessory for an investment, going with a classic silhouette and color from a heritage brand is a safe bet.” 

“The Jodie is still all the rage. Bottega Veneta continues to release fresh iterations of this style and we think shoppers will only fall deeper in love.”

“Time to bring this early aughts favorite that was in steady decline for a good 15 years back out of the Y2K wardrobe.”

“Chanel is so known for structured shapes, but people are really gravitating towards the more casual, easy form of the Chanel 22—and in a fun Y2K metallic aesthetic.”

“Consider watches the new real estate. We’ve seen average sale prices for luxury watches have increased each year, with Rolex and Cartier watches raking in the highest sales.”

“As the collection keeps growing and new colors are released, there’s no doubt that shoppers continue to be enamored by them. Both men and women are parking their money in Birkin bags.”

“When seeking pieces that are strong investments, think of classic wardrobe items like a blazer, cashmere knit or knee-length coat, or go for styles representing what a designer showed on the runway, like a signature print of the season. Accessory and shoe-shoppers should take note if items that have any strong brand signifiers (e.g. elements that are classic or iconic to the brand such as monogramming, identifiable logo hardware, or signature design details like woven leather). These things typically drive resale value up. Also, if an item is limited in production, can be considered ‘collectible’, or is difficult to procure on the primary market, these are typically signifiers they’re a strong investment. For bags, think Hermes Birkins or Telfar totes, and, for shoes, Mach & Mach and Amina Muaddi are great examples.” 

“This jacket is certainly an ‘outfit maker’. The piece that can be thrown over a jeans and a tee, or your athletic wear, and still have an easy statement look.”

“Whether cashmere, cotton, or silk, full length or single-buttoned at the chest, cardigans are a closet staple to take you from winter to spring and back again with playful styling along the way.”

“Loose leg trousers are battling jeans for their everyday easy wardrobe status, and are an item to add to your closet this year.”

Next: 11 Quiet-Luxury Bags That Are Low-Key, Anti-Trend, and Peak Cool

“After all-about-the-mini, something feels fresh about a chic pencil skirt. This vegan leather version from Nanushka has all the right levels of luxe.”

“An Hermès scarf adds vibrant pops of color and dozens of ways to style your outfit, whether it’s worn around your neck, in your hair, or as a handkerchief top.”

“Quality and craftsmanship are by far the most important qualities to look for in investment-worthy items. The goal is to invest in pieces that stand the test of time, so that even if you no longer find a use for them in the future, you can resell them to someone new. This is a much more sustainable alternative to buying fast fashion and letting it go to landfills after it goes out of style or gets damaged.”

“A good pair of jeans is an absolute must-have in your wardrobe! 501 Levi’s can be dressed up or down, and are super comfortable! There’s a reason this is one of the best-selling Levi’s jeans of all time… They have transcended decade after decade and will continue to do so for generations to come.”

“This bag has been iconic for decades and reimagined through the fashion house’s multiple creative directors over the years. It was one of our top-selling bags in 2022 and we have a feeling it will continue to be a must-have for seasons to come.”

“It’s been over 25 years since Hermes came out with the Oran sandals, and they are still iconic as ever. These have become some of the most desirable – not only shoes – but accessories you can own! Definitely a must-have for 2023’s spring and summer seasons.”

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