Bruce Sherman knows how to put on a show, which he has been doing to great acclaim for more than a decade at North Pond, the romantic Arts and Crafts hideaway in Lincoln Park. Earlier this year, he won the coveted James Beard award for best chef in the Great Lakes region, an honor that validates the durable appeal of his way of cooking: seasonal foodstuffs—local produce, artisanal meats, sustainable seafood—shined up with classical French technique.

But Sherman, 51, is also a husband and father of two (Emma, 17, and Kate, 11). And the last thing he wants to tackle on a day off is a complicated culinary project. When he and his wife, Joan, invite family and friends to their Evanston home, they generally keep things simple. For example, Sherman will make homey braised lamb shanks and winter spinach for Hanukkah with his dad, who lives in the city. For Christmas, which the Sherman family celebrates too, he’ll serve up hot-pressed panini—stuffed with prosciutto, pickled red peppers, and Wisconsin cheese—and a bottomless bowl of Chex mix. “That’s our tradition because everyone’s exhausted from getting up early and opening presents,” Sherman explains.

So he seemed like the perfect person to solve the stressful mind game that holiday entertaining can become: Should you try something new and exciting or satisfy the tradition-bound expectations of your guests? Besides that, how is it possible to cook everything from scratch without losing it?

At Chicago’s request, Sherman created a menu that kicks the usual festive dinner fare up a notch but is easy enough for the average person to manage in a regular home kitchen. No fussy ingredients. No recipes within recipes. The result is a tour de force: a sophisticated cocktail and appetizer pairing, a dramatic pork rib roast with a blizzard of hearty side dishes, and an elegant dessert that tastes positively restaurant-worthy.

His secret? Choose dishes that you can prepare largely in advance. Study his detailed game plan and you’ll see that it is possible to make a big, impressive meal with a relatively small amount of cooking on the day of the event—leaving you plenty of time to plump the pillows, sip a test cocktail, and catch your breath before the doorbell rings. “If something is so stressful that you can’t have fun, what’s the point?” Sherman says.

Just as important, he adds, is to buy the best-quality ingredients you can find. Anyone can set out a bowl of olives. But when you buy the freshest, brightest green Cerignola olives around (one good source for them is Graziano’s, at 901 West Randolph Street), half your work is done even before you marinate them overnight.

One of the first chefs to champion the Green City Market (the 12-year-old farmers’ market in Lincoln Park; held Saturdays in winter at the Peggy Notebaert Nature Museum), Sherman argues that a carrot is not always a carrot. Indeed, when I tested his recipe for balsamic-roasted root vegetables, baby carrots from the farmers’ market held up far better in cooking than did the organic carrots from the supermarket, retaining their crispness even after 40 minutes in a hot oven.

Finally, Sherman counsels, let go of the idea that you must make absolutely everything from scratch. In other words, give yourself permission to make strategic timesaving substitutions. Take the crust for his rack of pork, a clever twist on the traditional Christmas ham. Instead of using the gingersnaps from Sherman’s recipe, feel free to go with ready-made cookies, he says, so long as you eschew bland varieties for good ones with real spices, either from a bakery or the grocery store.

As for his silky-smooth bourbon applesauce: It couldn’t be easier to make. In a pinch, though, simply add a splash of nice bourbon (Sherman likes Rowan’s Creek) to a good-quality applesauce and warm it gently before serving. Don’t forget to set aside a booze-free portion for the kids.

And you can prepare the components of the dessert—poached pears served with a rosemary-flavored custard and delicate orange-almond tuiles on the side—in advance. Or skip the sauce and cookies and match the pears with either of these two supereasy accompaniments: a scoop of eggnog ice cream (plain vanilla works, too) or a soft cheese that becomes custard-like at room temperature. Sherman recommends procuring a wheel of Rush Creek Reserve, a glorious bit of aged raw cow’s milk from the Uplands Cheese Company in Dodgeville, Wisconsin. (Be sure to reserve one in advance from Pastoral, at 53 East Lake Street, or Provenance Food and Wine, at 2312 West Leland Avenue, because every week’s supply of this limited-release cheese reliably sells out.) “You could even dip the gingersnaps into it,” Sherman muses. “It’s just magical.”

He’s talking about the cheese. But chances are you’ll feel that way about the whole evening.