How to Spend It: Invest

Want some bang for your buck? Sometimes, dropping serious coin is the smartest play in town.

Frame by Frame 

Investing in art is very similar to investing in the stock market: you can either bet on start-ups (a.k.a. emerging artists) that may either go great guns or go belly up; or you can look for blue chip stocks (established artists) who you think are undervalued. Option #1 is sexy, but Option #2 is smart. Take Jack Shadbolt’s recent show at the Equinox Gallery. At the time of his passing in 1998 Shadbolt was the preeminent artist in B.C. and his reputation hasn’t faded. Shadbolts aren’t cheap—prices at the Equinox show ranged from $15,000 to $20,000 for good sized pieces—but compare that to the prices of his contemporary E.J. Hughes, whose large canvasses can now top $1,000,000, and they seem like a very solid, undervalued art play.

Tick Tock 

The Daytona and the Submariner represent the dynamic duo of investment-grade Rolexes (Paul Newman’s personal Daytona sold for $17.75 million last November), so those looking to buy a new model with potential resale value might want to look at one that hasn’t yet attracted as much frenzy: a good bet might be the classic Explorer (not the Explorer II), which has the same legendary history of those other two (its predecessor was the first to see the top of Everest), and the same rugged good looks, but it sits at a relatively easy entry point (for a Rolex, that is) of $7,500. At 39 mm, it’s a nice size—big, but not hulking—so it’s likely to be in fashion in the future, assuming the ginormous watch craze continues unabated. Also, it’s beautiful: simple, handsome, timeless. Remember—always keep the box, paper and even receipt pristine—they’ll add to the valuation in the years to come.,

Not-So-Fast Fashion

This is an easy one: 99.9 percent of clothes go down in value. The exceptions?

1. Any Nike sneaker you need a raffle for2. Hermès Kelly bag3. Hermès Birkin bag4. Supreme x Louis Vuitton5. Adidas Yeezys

Garage Goods 

As a general rule, if you’re buying a new car, your odds of making money might be a little thin. But let’s narrow it down using a few basic rules: SUVs never appreciate, no matter how rare; ditto sedans. And assuming you can’t get on the list for some limited-edition Ferrari, we’re left with this big bite: the Porsche 911 GT2 RS, a $334,000 car that is the most powerful 911 car ever made by the company (700 hp worth of power, in fact). Older 911s have shot up in value lately (especially anything with an air-cooled engine) as collectors scramble to snap up historical icons from the world’s most famous sports car. The good news? You can easily drive this baby around town—something that can’t be said for your Lamborghini. The bad news? Every kilometre you log will detract from the value when you go to sell. The wild card? Porsche has not announced how many of this model they’re making, so if they keep cranking them out, it could affect the long-term value. If they don’t, this is a good bet to wow at the auction block in 2030.

Cheers to That

Back in 1993, we had wine guru Anthony Gismondi choose a handful of wines that he thought were good bets, investment-wise, and darned if he didn’t end up beating the S&P 500 by 90 points. Fast-forward to today, and the fermented grape juice landscape has changed (a bottle of Lafite Rothschild will now set you back $3,000), but we’ve asked Gismondi and Wine associate Treve Ring to suss out a new crop of investment-grade bottles.

1.  Domaine Jamet 2013 Côte Rôtie, N. Rhône, France, $140Affordable still from what is considered by many to be the pinnacle of Northern Rhône syrah. Tightly knit and highly structural, concentrated yet finessed, with heaps of savoury stoniness that will take years to yield.

2. Château Beychevelle 2014 St. Julien, Bordeaux, France, $170Epitomizing the smooth and ripe fruit St. Julien is known for, this vintage is especially perfumed and expressive, with density and amplitude that allow this regal medium-bodied Bordeaux to age impressively.

3. Champagne Jacquesson NV Extra Brut Cuvee No. 739, Champagne, France, $86.86A mature, lightly toasty and creamy wine, with a backbone based on the leaner, erratic 2011 vintage and all the best fruit went into this bottle. Native ferment, one-third reserve wines and aging in large wooden casks add detailing and support to carry this long haul with character and grace.

4. Tenuta Poggione 2012 Brunello di Montalcino, Italy, $80Fantastic value for this confidently quiet brunello, one of the stars of Montalcino. Richly saturated with dark fruit, but with a rush of vibrant acidity to the bright, tight finish. Will reveal in time.

5. Ridge 2014 Monte Bello, Santa Cruz Mountains, California, U.S., $300Understated, humble and authentic are not words that come to mind when thinking California cabernet blends, but the prestige and respect for Ridge’s Monte Bello is deserved. Inherently complex yet refined, with graphite, dark chocolate and cassis streaming the long length of this graceful wine.

See more from our How to Spend It package and put your money to work with the best ways to indulge, invest, give back and outsource your life.