How to pick wine like a boss Our sure-fire system for getting the perfect bottle every time

Way back in the day when I was a waiter at a fancy shmancy restaurant in downtown Portland, I’d often have to recommend wine to go with whatever customers ordered. To help us out with that, we’d actually have representatives from different wineries come out and do presentations to the wait staff and we’d get to taste all the wine and talk about how to pair it with food. The chef would break out the menu and sometime even prepare some food.

Heathman Hotel in Portland

This is the Heathman Hotel restaurant where I worked. It had a French chef and everything.

We’d hear all about how the wine was made. We’d hear about oak barrels and wine blending and aging. We’d learn some great adjectives for describing wine tastes.

Apparently the more bizarre the description you use the more you sound like you know what you are talking about. So descriptions like “3 day old Cheerios” or “Tootsie Roll dusted with cinnamon” would be great wine descriptions. The more wacky and awesome your description was, the more the wine representatives would smile and nod with delight.


Do these remind you of a big, hearty Cabernet Sauvignon? Me either, but the wine reps ate this kind of thing up. (The description, not the Cheerios.)

When it came to food pairings there were all kinds of rules. Hearty wines like Cab went well with hearty foods like steak. Sweet white went with spicy. Don’t remember much else, but suffice it to say there were a lot of them to wade through to get it right.

steak risotto beans dinner plate

This meal would call for a red wine.

Mostly, though, I found that most people really didn’t know anything and you only needed to SOUND like an authority to pull it off. So I memorized a few rules and had some sweet descriptions I could pull out to describe the wine if needed.

Trouble was, it all tasted the same to me because I didn’t drink enough of it to develop a wine palette. If there really was anything to the whole pairing wine with food business I never really figured it out. I was just good at faking it. I suspect many people are faking it, and there’s nothing wrong with that.

wine drinking

Here's Rita and kids pretending to be snooty wine drinkers last Christmas. (No, we don't give our kids wine. They prefer soda.)

Still, even if you get over the idea that choosing wine is a special science, that doesn’t mean it’s easy to do it. There’s a lot of bottles on a lot of shelves in most stores. How do you figure out which one to take home with you?

Rita and I have managed to develop a system for wine selection that works great for us. If–like me–you’ve ever had trouble with the traditional method of understanding grape variety, wine growing regions, vintages, growing seasons, and food pairings, you might want to try our simplified system.

table setting with wine glass

Rita and Cane Wine Selection System

Step1: Choose white or red

Here’s how we pair it with food. Suppose you are serving green food. As best as I can recall from my art school training red is the complementary color of green so it makes a complementary color scheme, which is supposed to be pleasing to the eye. Pair it with brown stuff like steak and you have an analogous color scheme. That’s a good one too.

color wheel

OK, just kidding. We don’t really use the color wheel to pick the wine color.

We tend to pair red wine with any food that we like to cook. Why? Because we like red wine and we like the food that we cook. How perfect is that? We like to drink red wine while cooking, so we just continue drinking it with the meal. Makes sense.

cane pouring wine

This is a joke, too. Not really cooking with wine here--making mulled wine last Christmas.

White wine goes well with hot, sweaty days. When it’s too damn hot to cook we like to drink white wine. So it goes well with take-out, pbj’s, chips and guacamole, watermelon, ice cream, and Adirondack chairs in the back yard. It goes really well with a couple of ice cubes if the temperature is above 95. So, just ask yourself this question if you want to make it easy:

Is it damn hot out?

Yes- White wine.

No- Red wine.

cane in hammock

This was definitely a white wine day.

Step 2: Consider Price

How much do you want to spend on that bottle of wine? It has to be under 10 dollars for me. Since it all tastes mostly the same, I don’t subscribe to the idea that the more you pay the better it is.

I usually start with the cheapest and work my way up as I’m scanning the aisles for bottles. Once I’ve established my price point, it usually eliminates about 90% of the bottles in the store. Much more reasonable to work with. I’ll start by looking at the cheapest bottles and move up in price until I find something reasonable.

barefoot and flipflop

Two wines we like. How can you go wrong with bare feet and flipflops? They just go together, like pb and j. (And you can drink them with pb and j, if you're so inclined.)

Step3: Find a cool label

OK, now you have to start looking at the labels. What we are looking for is something cool. No boring or stuffy looking labels. We want something fun or funny or interesting. Something that makes you smile. It could be cool or irreverent or whacky. It could have a kick-ass font face or a great name.

The label  matters because:

a) You have to find some way to choose;

b) It’s easier to pick a cool label than to memorize all the rules you’re supposed to know about buying wine;

c) It’s nice to having something fun on the table to look at when you’re lingering after the meal.

red wine in glass

To sum it up…

I find the cheapest bottle in the store and pay up to a 2 dollar premium for a kick-ass label. It might be a Merlot, or a Cab, or a Pinot Noir. I never remember which one of these I like best or if they taste different in any way. It might come from California, or Oregon, or Australia, or Italy even. Don’t much care about that. I know that the Italians and French are supposed to make great wine but they make horrible boring labels. Who wants to look at that? Plus they usually cost more than my price point.

And that’s it.  It’s a great system that has worked out very well for Rita and me. We always leave the store with a cheap, good bottle of wine with an awesome label. We drink it with delight and the full confidence that we picked the perfect bottle for us.

two wine glasses

I’ll soon share our similar system for picking plants for the garden. Works every time!

rita shopping for plants

Plants are a little harder because they don't have cool labels.

Now it’s your turn!

Tell us how you choose wine…Will you be pairing any with your Memorial Day picnics this weekend?

Credit for color wheel image