BUY, HOLD, SELL

1988 Honda VFR750R Type RC30

This World Superbike Championship–winning motorcycle has long been coveted by collectors, and now Gen X buyers are driving the RC30 toward a six-figure future: This model, with just 5,900 miles on the odometer, sold for $60,000 in April.

Jessie Willcox Smith (1863–1935)

Smith’s Little Miss Muffet is the “Mona Lisa” of children’sbook drawings, but her work remains relatively affordable ($300,000 for the composition above). With illustrations skyrocketing into the millions, that won’t last long.

Nike Air Force 1

This classic is celebrating its 40th birthday with renewed popularity. This Virgil Abloh–designed pair sold for $150,000 in February 2022, and the market is ready for takeoff.

1930s Brough Superior SS100

A masterpiece from motorcycling’s Golden Age, the SS100 is a blue-chip investment. Older editions are already selling for more than $500,000, and 1930s models are sure to appreciate.

Blanche Lazzell (1878–1956)

One of the country’s most revered early-20th-century Modernists, Lazzell gained fame through lush oils and vibrant woodblocks like this $30,000 print. Prices are holding firm, but her moment is near.

Nike Skateboarding Shoes

A passionate collector community makes investing in Nike’s boarder kicks a walk in the skate park, especially SB Dunks: The FLOM (For Love or Money) (above) doubled in value to $120,000 since 2020.

1950s Vincent Series-C Black Shadow

Once the fastest vehicle on the road, capable of 125 mph, the Black Shadow is starting to head downhill in value. This Best in Show winner from 2010 at the Concours in Stafford, England, fetched $70,000 last July, 30% of 2016 prices.

Georgia O’Keeffe (1887–1986)

Auction houses and galleries can barely keep up with demand for O’Keeffe, already a record-breaker with her $44 million “Jimson Weed” (above). Satisfy collectors’ appetites by cashing out now.

Yeezy

Kanye West’s footwear line was cooling off before he parted ways with Adidas: Few styles have fetched five figures since April 2021, when his Grammy-worn Air Yeezy prototypes (above) set a $1.8 million record.