Before Galen entered the picture, Hilary Frayne – daughter of an appliance salesman – had a vibrant middle-class upbringing in Dublin, Ireland. She was particularly drawn to the work of the Bloomsbury Group,  a famous circle of English authors, painters and intellectuals that included the great Woolf, Vita Sackville-West, Vanessa Bell and Duncan Grant, the artist who created one of her very first pieces. “It was a voyage of discovery through reading that finally brought me to be interested in art,” she says. While working as a fashion model around that time, she caught the eye of Galen, who came to Ireland to set up a grocery chain. He was following suit in the entrepreneurial successes of his grandfather George and father Garfield, who thrived in the food industry. A few years later, the two married, simultaneously sparking a union of art that, among a list of things, would later transmit to their children, Alannah and Galen Jr. “We became very interested in drawings per se, so we started to collect French and Italian Renaissance earlier drawings … In those days it was what one could afford, and we felt very fortunate to have been able to buy them at the time because prices for paintings were crazy,” says Weston, whose last name currently sits second on the list of Canada’s wealthiest, with an estimated net-worth of $8 billion, according to Canadian Business magazine.

Alannah vividly remembers growing up in a house where the walls could talk, particularly in the green language of new realism artist Christo, whose work her parents avidly collected. “Ever since I was a little kid I was surrounded by conceptual art, so I remember writing my final exam at Havergal [College] all about Christo and trying to defend the fact that his art was ephemeral, it was temporary even though it cost millions of dollars to create, and then it was gone within a few days,” says Alannah. She has been lauded as a transformative force in her current creative director role at Selfridges, the high-end British department chain her father famously added to an empire that encompasses Loblaw Companies Limited and Holt Renfrew & Co. in 2003. Coincidentally, it was Alannah who would introduce her parents to the world of contemporary art, which she discovered during her studies at the University of Oxford and subsequent stretch as an arts-beat journalist for London’s The Daily Telegraph. “It’s all my fault,” she says, laughing in her sprightly tone while looking back on her mother’s amusement when she would come for a visit and find video installations in the bathroom. Alannah’s laugh elevates and reddens when she tells the story of the time she posed nude for her friend, artist and photographer Beth Derbyshire. “I posed for her undergraduate degree work and my dad was a little shocked so he ended up buying all of the work … so that was a great introduction!”

With the curatorial influence of her daughter, Weston’s newfound affection for contemporary art would inevitably become the pulse of a private residential community her and Galen Sr. established in Vero Beach, Florida more than two decades ago. As creative director, Weston was at the helm when ground broke on Windsor, a 416-acre “village by the sea.” Consisting of 350 uniquely designed luxury home sites, its complementary grounds reflect Weston’s affinity for architecture and horticulture. Windsor was built by Andrés Duany and Elizabeth Plater-Zyberk, architects of the new urbanism movement, on a verdant barrier island between the Indian River and the Atlantic Ocean. “Everything there was designed by my parents, really carefully, to kind of reflect all the essential human needs. So, of course, it’s a very privileged place, but at the end of the day, no matter how we live we all want to live in communities, we want to live close by each other, we want places to go to eat, to meet our friends, we want to play; we want to be inspired, and I guess art is part of that,” says Alannah, which is why she made a monumental move in adding a not-for-profit art gallery to Windsor in 2002 while filling in for her mother, who was serving her final year as lieutenant-governor of Ontario at the time. Suffused with natural light, The Gallery at Windsor has featured the works of important contemporary artists such as Peter Doig, Ed Ruscha and Alex Katz. Even the Weston family’s eccentric leading man Christo and his wife, the now-late Jeanne-Claude, have been by for a discussion. Of all its achievements, it’s Weston’s newest project that has her on the edge of her seat.

It’s an idea that came to light under a veil of stars at Windsor when the Westons were hosting Iwona Blazwick, director of the Whitechapel Gallery, London’s century-old art space acclaimed for premiering modern icons like Jackson Pollock and Pablo Picasso. “It just flowed over dinner one night,” says Weston of the conversation that led to a curatorial collaboration in which Whitechapel Gallery will bring three annual exhibitions to The Gallery at Windsor. “In a way it’s kind of paradoxical,” says Blazwick. “We are absolute opposites: the Whitechapel Gallery is in the east-end of London, it is the most dense, urban, edgy location you could possibly imagine, you know, the sirens never stop … so this seemed like a really exciting idea to go to a place which was like paradise: it’s tropical, it’s on the ocean, it’s got the most incredible lush vegetation,” she remarks, of an east-meets-Weston partnership that begins December 2011 to coincide with Art Basel Miami Beach.

For a range of reasons that include the scope of her cultural influence and geographical context, the vibrant, rhythmic screen prints and wood block editions of renowned Brazilian contemporary artist Beatriz Milhazes were selected for the first solo exhibition. “One doesn’t necessarily plan for any of these things, they just take on a life of their own,” says Weston.

Such off-the-cuff undertakings may be a recurring thread in Weston’s life, but it’s never before measuring depth that she decides to dive into a blue pool. Whether it was her decade-long tenure as deputy chair of the board for family owned Holt Renfrew, or her notable term as lieutenant-governor where she fought to bring awareness to youth homelessness and women’s issues, every venture is carefully considered.

Her cautionary approach was perhaps most transparent in 2002, when she accepted the ambitious philanthropic post of Renaissance ROM Campaign Chair, pledging to help raise hundreds of millions of dollars in Canada’s largest cultural fundraising movement. “She took a lot of time and interviewed our board chairs herself before she finally committed herself to lead that campaign,” says the ROM’s former director and CEO William Thorsell, adding that once she came on-board she was very willing to work in the trenches. Thorsell recalls many instances where he and Weston would park their car outside a potential donor’s office tower and strategize over the approach they would employ to get that person to make a massive contribution. “We’d come out and high-five after, so you know, I got to know her well enough that we could do this, but it’s not the Hilary Weston most people see. She’s actually got a great wit, she’s relentless, she doesn’t take ‘no’ for an answer in the sense that if somebody says no, she’ll say, ‘that means not yet.’” Her effective persistence even made headlines in The New York Times, which applauded her for famously persuading businessman Michael Lee-Chin to donate the $30 million that revolutionized the architectural face of Bloor Street with the Daniel Libeskind-designed Michael Lee-Chin Crystal. “So much of these things are about understanding and respect, because I think that you can’t expect people to give you money, you’ve got to hope it’s a good fit and that they believe that it’s real,” says Weston, who elevated the campaign with a gift of $20 million split evenly between her and her husband, and The W. Garfield Weston Foundation. “You have to learn how to give money away, that is a lesson in itself.” On another philanthropic page, The Hilary Weston Writers’ Trust Prize for Nonfiction recently praised its first winning author with a substantial prize of $60,000.

Like acclaimed contemporary artist David Hockney has said, “The longer you look, the more you see.” Watching Weston articulate her passion for the arts, philanthropy and her upcoming Windsor collaboration is a bit like dipping photographic paper in developer and seeing a portrait gradually emerge. Canada’s closest connection to the royal family is an astute businesswoman, exemplary wife and fun-loving mother, who, according to her daughter, is filled with Irish catchphrases and wise advice like, “Always leave a party when you want to stay a bit longer.” In contrast to her descriptive interpretation of the Toulouse-Lautrec piece, it takes Weston a few moments to harness her definition of a happy life. Not for a lack of words, but for an abundance. “A happy life is being curious in life, and learning through your experience and enjoying it as a result of what you’ve learned … I think it isn’t just one thing, because curiosity brings you into so many different areas and you discover so much about yourself by learning through other people, and one’s always seeking the spiritual in life and I think sometimes you find, and sometimes you don’t, that it comes and it goes, but to have them all is really, truly, the sweet life.”
www.windsorflorida.com
www.westonfoundation.org

AUBERGE DU POMMIER
Huîtres &  Caviar
Peter Oliver: I feel that Chef St. Jaques takes oysters to the next level with this dish. The poached oysters are placed on a bed of leek velouté, then topped with toasted brioche and caviar. It’s magnificent.
Boeuf Quatre Façons
Michael Bonacini: I love this dish as it gives you the opportunity to taste not one, but four styles of beef: ribeye, short rib, oxtail, and a ragoût. This is a rich dish, perfect for a chilly winter day.
Macaron
Oliver: These French macaroons just melt in your mouth. They are the perfect finishing touch to a wonderful Auberge du Pommier meal.

BANNOCK
Bannock Bannock
Bonacini: House-smoked salmon and cream cheese on freshly made bannock.  This is such a fun dish that blends Canadian traditions in a unique and interesting way.
Arcadian Court Chicken Pot Pie
Oliver: When we first announced that we were opening a restaurant in The Bay, people would stop me in the street and ask me about this pot pie! It has been a Toronto family favourite for many years, and we are thrilled to carry on the tradition.
Sour Cream Donuts
Bonacini: Real Canadian, eh?
Oliver: We know we couldn’t serve Canadian comfort food without a glazed donut on the menu. These are warm, doughy, a little crispy on the outside. Simple food – elevated.

OLIVER & BONACINI CAFÉ GRILL
Grilled Calamari
Bonacini: This calamari dish is adapted from the Jump lunch menu, and is one of my favourites.
O&B Macaroni and Cheese
Bonacini: This is classic mac and cheese for grown-ups.  With aged white cheddar, goat cheese, roasted chicken and sweet garden peas, it’s a fun spin on an old favourite.
Carrot Cake
Oliver: This is a carrot cake for real carrot cake lovers – moist, perfectly spiced and topped with a not-too-sweet cream cheese icing.

LUMA
Burrata
Bonacini: I love that this dish is rich and creamy but still feels light.
Steak Frites
Oliver: This is such a classic, timeless dish – a fantastic match with a bold red.
Opera Cake
Bonacini: A perfect end to dinner and a movie! If you forgot to buy your date a snack, the popcorn ice cream and caramel popcorn will more than make up for it.

Peter Oliver and Michael Bonacini Guest Food Editors
Two of Toronto’s best-known culinary entrepreneurs put it all on the table nearly two decades ago when they partnered to open Jump Café and Bar in 1993. At the time, Peter Oliver was a thriving Toronto restaurateur, and Michael Bonacini was the executive chef of Centro. Today, their lucrative food enterprise dots the city with restaurants and event spaces, which include Jump, Canoe, Biff’s Bistro, Auberge du Pommier, Oliver & Bonacini Café Grill, Luma, O&B Canteen, Malaparte and Bannock. Oliver is also the founder and president of The Stephen Leacock Foundation, a charitable organization that helps disadvantaged children in Canada and the developing world. www.oliverbonacini.com

Glenfiddich Snow Phoenix
Nothing brings a capsized day to shore better than a nightcap. MacPhee chooses to get whisked away by the warmth of Glenfiddich Snow Phoenix single malt scotch whisky. www.glenfiddich.com

Jaguar XF
MacPhee chose this mid-size luxury ride for all the right reasons: it’s easy on the eyes and the environment. This car gets him from A to B and beyond in sophisticated style. www.jaguar.com

Rado DiaStar Watch
An invariable element of MacPhee’s wardrobe is Rado’s Integral two-tone watch with its sapphire crystal elegance and high-tech psyche. www.rado.com

Prada Chelsea Boots
MacPhee slips on his black leather Prada Chelsea boots to give him that extra kick. www.prada.com

Ermenegildo Zegna
We communicate with our words, actions and even our attire. For MacPhee, Zegna’s bespoke suits do all the talking. www.zegna.com

Isaac Hayes
When it comes to music, MacPhee has Hayes fever. The songster behind the musical score for Shaft impresses with Hot Buttered Soul. www.isaachayes.com

Stewart MacPhee is president and CEO of Toronto public relations firm PUNCH Canada Inc. www.punchcanada.com

1. Bottega Veneta Eau de Parfum, Body Lotion and Shower Gel: Renowned designer Tomas Maier debuts a decadent, exclusive scent that’s perfect for that special person in your life. Available at select The Bay stores and Holt Renfrew locations across Canada.

2. Kodak EasyShare Camera: Capture those special moments with this easy-to-use point-and-click camera.

3. CHI Straightener: All frizzed out? Get straight, shiny locks with the power of ceramic technology.

4. Dimples Bracelet: An earth-friendly silver charm bracelet that captures the fingerprint impression of a loved one, newborn infant or pet.

5. Chanel Sublimage La Crème: The ultimate in skin regeneration, this silky cream nourishes your complexion with moisture and radiance while firming facial contours.

6. Keurig Special Edition Brewing System: Good morning, coffee connoisseurs! This special edition single cup brewer is a great holiday gift for those on the go or a friend that entertains.

7. Philip Stein Timepiece: Beneficial to life and health, the frequencies of a Philip Stein watch provide a lifestyle experience that is more resilient and adaptable to stress.

8. Hydra Thermal with Light Therapy Facial Gift Card at King Country Day Spa: This lifting facial with a gentle micro current and light therapy session stimulates the collagen in your skin at the cellular level.

Congratulations to our winners, Eileen & Jim Wright!

Thank you to the following sponsors: Cupido, L’Oro Jewellery, Coty Canada, Chanel, Keurig, King Country Day Spa

“This is a very exciting event,” says Tim Elgar, director of charge cards for American Express Canada, explaining how the private shopping affair, reserved exclusively for Centurion members, awards after-hours access at four of the city’s most coveted boutiques: Louis Vuitton, Cartier, Hermès and Gucci. Valet is at the ready, champagne cascades, exquisite hors d’oeuvres are served, and handsomely attired personnel wait on cardholders hand-and-foot. Every guest is also given a special gift before leaving each shop. Gucci, for example, presented Guccissima leather card cases personalized with gold initials.

With no pre-set limit, the Centurion Card is a mark of affluence and social standing, simultaneously removing barriers and opening doors, granting cardholders perks such as hotel upgrades, bonus reward programs and access to airport lounges. There’s something enigmatic about it. As Elgar notes, “We like to think about it as similar to carrying a private club membership in your wallet.”

A rare beast of personal finance, the ‘black card’ is available by invitation only, requires a $5,000 initiation fee and $2,500 annual fee. And while AmEx won’t disclose further qualifications, you can confidently assume it requires an exorbitant amount of income to even be considered. A fact made clear by the unabashed luxury on display at Blackout on Bloor.

“We reserve it exclusively for the top tier of our card member base here in Canada,” says Elgar, describing the jet-black, hand-forged, engraved and embossed piece of titanium. “There’s really nothing else like it on the planet.”

The perks don’t cease at the boutique. Centurion members have a personal concierge service at the ready for around-the-clock requests that range from the simple day-to-day, like ordering business cards, to the extraordinary. Elgar explains how one cardholder, for example, wished for a cast member of the Gone With the Wind musical to hand his wife flowers during a performance – the request was fulfilled. “We work very hard to understand each Centurion Card member at a very personal and meaningful level so that we can cater all our recommendations and the access we provide for them at an individual level.”

As the shopping winds down, the Gatsbyesque evening fittingly flows to La Société for drinks in cosmopolitan style. Bottles of bubbly pop, freshly uncorked vintages breathe, and no one bats an eye. But why would they? Their black cards have it covered.

www.americanexpress.com

My husband and I started a family foundation in 1991 because it seemed like a good thing to do. The next year I joined  the NY Women’s Foundation Board. On this board, you don’t just read proposals, you go to Coney Island and talk to ex-heroin addicts about HIV and prostitutes. I learned a ton.

I didn’t travel far when our four kids were little, but I travelled to all sides of my city. In New York, it’s all here. My leash made me go micro before macro. I saw the local political landscape. I got onto a zillion non-profit boards and volunteered in little organizations. I got to see what people were stressed out by, whether lack of serviceable office equipment, or rats and guns.

When I finally travelled overseas to Liberia and Egypt, I was stunned — both by the severity of the problems, and by how people had the same struggles all over the world. The issues at job-training programs in Morocco were the same ones I heard in New York. I’m glad I first took the time to learn deeply about the problems at home.

With our family fund, called the Daphne Foundation, we did something smart. We took the time to list the grantees that really moved us. During the reflection process, it was torture to say ‘no’ to requests, but we needed time to get clear. We discovered that we liked to focus on ‘adolescent’ organizations: groups that are no longer “the flavour of the month” for funders although they haven’t yet reached institutional stability. Equipped with this focus, we went seeking our life partners. We have been funding some of the same groups now for 10 years. The Daphne Foundation, now endowed and giving $850,000 a year, has been a third of my total giving.

I recently self-financed an incredible film by and about women peacemakers in Liberia called Pray the Devil Back to Hell. I am happily using my last name to get it publicity, glad that I can put both my money and privilege to such powerful use.

The position I am in life is sometimes challenging. I don’t enjoy that many people are terrified of me, if not because I’m wealthy then because I have a famous family name. The more people are afraid of or intimidated by me, the less they tell me the truth and the harder it is to truly connect. Every room I walk into I am seen as holding the checkbook to solve everyone’s problems. Sometimes I feel like I’m going to die from all the people who want money from me. But if that’s the price for engagement and self-respect, I’m willing to pay it.

A lot of people give away the froth on their cappuccino. Why stop there? Over the past 10 years, I give all the income I don’t spend. I’ve given away about a third of my net worth, although it has come back to me as quickly as I’ve given it away. I’ve started making million-dollar grants payable over four to five years.

But bolder giving isn’t just about grant size; it’s about being out in the world and working with other people. I’m far richer a person because of it.

Excerpted from an interview with Abigail Disney on www.BolderGiving.org, where over a hundred profiles of bold givers can be read.

Breville Espresso Machine
To keep his days feeling short and sweet, Birchall prefers the steamy precision extraction of The Dual Boiler espresso machine. www.breville.ca

Progressive Nutritional
In the progressive world we live in, one must be conscious of keeping healthy. This is why Birchall starts his day with a multivitamin that complements his dynamic lifestyle.www.progressivenutritional.com

Ford Mustang Shelby GT500
When driving in the fast lane, Birchall beckons the torque of Ford Mustang’s Shelby GT500. With a 5.4-L supercharged V-8 engine, fellow roadsters are left in the dust. www.ford.com

Rolex
The watch you choose to wrap around your wrist can say a lot about your character. With a sea of brands, sizes and styles to choose from, Birchall sticks to the classic eminence of Rolex Deepsea. www.rolex.com

Milwaukee’s M12 Heated Jacket
Birchall doesn’t let the cold air give him cold feet when it comes to staying active outdoors. Instead he slips on Milwaukee’s M12 Heated Jacket. www.milwaukeetool.com

Jim Birchall is founder of Birchall & Associates Inc. www.birchallpr.com

For Immediate Release
Ronn Torossian totes his top-selling public relations book For Immediate Release wherever he goes. www.ronntorossian.com

Philip Stein
When he’s keeping track of time, Torossian does it with Philip Stein Prestige. www.philipstein.com

Hint Water
Torossian drops a Hint about seeing his glass half full. www.drinkhint.com

Ronn Torossian is CEO of New York-based PR firm 5WPR. www.5wpr.com

2. If you’re looking for motivation, look to your wrist for inspiration. With the diamond-encrusted words “Keep Calm and Carry on” strewn across the ebony cuff of this sparkling bangle, you’ll find the strength to get through anything.

3. Made from red and white crayons, Herb William’s The Color of Luck dice literally melds tools of art with tools of chance – and the result is nothing short of a winner.

4. Turn your bottles of vino into sparkling gems with these unique bottle stoppers that dazzle with natural amethyst and crystal spikes.

5. Straight from the reels of classic Hollywood sci-fi, Kim Kardashian’s latest line of Beach Bunny Swimwear is out of this world. www.beachbunnyswimwear.com

6. Originally released in 1963, Rolex’s Cosmograph Daytona was designed with the professional racer in mind. Its purposed mechanisms allow drivers to measure circuit time and average speed. www.rolex.com

7. With a 14-karat gold-plated buckle holding a princess-cut amethyst as its crowning jewel, this regal belt is reminiscent of a royal family’s prized heirloom.

8. This unique Infiniti G37 was hand-painted by Montreal artist Heidi Tailler, and auctioned during Masquerave, a culinary event in Whistler, British Columbia that raised funds for the non-governmental organization One Drop. www.infiniti.ca

9. A minimalist, modern masterpiece, the Qlocktwo Touch uses a stylish matrix of letters, as opposed to numbers, to register time. Perfect for that eccentric techie.

10. A unique twist on vintage furniture, this hot pink chair comes upholstered with patterned fabric that demands to be seen.

11. Delivering best wishes, I-love-yous and congratulatory praise in the form of majestic floral arrangements, Dizennio Floral is your first pick. After all, you never know what can blossom from the right bouquet. www.dizenniofloral.com

12. If your thumb is every colour but green, this simple hand-blown glass terrarium is easy to tend to – a pleasant and distinctive centrepiece.

13. A look Audrey Hepburn would adore, this Jimmy Choo clutch is an elegant accessory for those moonlit galas. www.net-a-porter.com

14. For the conscious consumer, Superior Seating Hospitality donates $50 to the Princess Margaret Hospital from the sale of each of these ribbon-shaped chairs. www.superiorsh.com

15. Clive Christian’s No. 1 Perfume is heralded as the world’s most expensive perfume. Using exquisite and rare ingredients, this scent will have you smelling like gold. www.holtrenfrew.com

16. Her eyes will sparkle when she beholds the wondrous beauty of the spectacular pieces and custom creations of Valente Jewellers. www.valentejewellers.com

Items 1, 2, 3, 4, 7, 9, 10, 12 available at www.vivre.com

2. The AvenDale Located in Toronto’s Forest Hill neighbourhood, the luxurious lifestyle of The AvenDale  gleams with hotel-style amenities and interiors by Gluckstein Design. www.minto.com

3. Shangri-La Like the manifestation of a fabled paradise, the Shangri-La appears in a stunning display, bringing the luxuries of a prosperous kingdom with it. www.livingshangri-latoronto.com

4. 277 Davenport The clean, modern design of 277 Davenport gives a sharp, metropolitan esthetic that melds perfectly with the city’s fashion-forward mentality. www.277dav.com

5. One Bloor A monument to the spirit of the city’s bustling core, One Bloor reaches for the heavens, towering over Toronto with wonder and affluence. www.onebloor.com

6. 1717 Avenue Road Without pretence or ostentation, 1717 Avenue Road manages to capture the prominence of this celebrated area through a soft look and artistic landscape. www.tributecommunities.com

7. Schoolhouse Loretto College’s traditional brick façade has been enhanced with contemporary condo living at Schoolhouse – Empire Communities’ latest venture into The Annex. www.schoolhouseannex.com