The 50 Most Stylish Moments of 2011

Style (noun)

1. A distinctive appearance, design, or arrangement

2. Elegance and sophistication

— Oxford English Dictionary

Whether walking the red carpet at the latest high-profile event or inspiring hushed whispers of admiration (or God forbid, disdain) at that chic cocktail do, the ensemble in which one steps out can ultimately prove to be a make-or-break moment; most notably for style-watchers like us at The Style Observer. As we usher in a new year and keep our well-trained lens on the coifs, dresses, accessories, suits and, of course, the shoes of the style-savvy and the uhm, fashion challenged, we look in the rear-view mirror at the head-turners who delivered the most stylish moments of 2011 between the pages of SO and Page 2.


Songstress Alaine Haughton made an ever-so-stylish appearance in this mint green strapless number as a guest at the nuptials of reggae crooner Jah Cure -- Siccature Alcock -- and Kamila McDonald at Tryall back in August.

Ali & Yussuf

Ali Lue and husband Yussuf Migoko seemed to channel the fabulous Kimora Lee Simmons and Djimon Hounsou at the Smirnoff Xclusive New Year's Eve soirée a year ago.

Hlison & Harvey Lyn

Harvey and Alison Lyn made a hot duo as guests at the Kim Edwards/Alfred James Hamilton nuptials February last in Atlanta.

Annmarie Vaz

Ann Marie Vaz, wife of Member of Parliament Daryl Vaz, gave a formidable nod to our local designers in a fabulous gown by Shenna Carby, the 2011 Mission Catwalk winner, when she appeared at the American Friends of Jamaica Annual Hummingbird Gala at the Capitale in New York City November last.

Ashley Martin

A beaming Ashley Martin (right) copped the well-deserved title Avant Garde Designer of the Year, as her mirrored creation, The Shape of Glass, modelled by Saint International's Danielle Bryan, caught the attention (not to mention the lights), of the judges and audience last March on the East Lawn of Devon House.


The voluptuous Barbee turned her, dare we suggest, finer assets in the direction of photogs on the pink carpet of the EME Awards on the East Lawn of Devon House in March.

Bernadette Barrow

NCB Assistant General Manager - SME & Retail Bernadette Barrow played gracious host (in shimmering silver compliments of Signature's Boutique) to guest speaker Wilfred Emmanuel-Jones, British businessman who helms the Black Farmer line of products, at the NCB Nation Builder Awards at the Jamaica Pegasus Hotel last October.

Caron Chung

American Friends of Jamaica (AFJ) executive Caron Chung dazzled in this strapless figure-hugging gown at the 30th Annual Hummingbird Gala at the Capitale in New York City back in November.

Deborah Newland

This strapless, floor-length silver gown with triangular black detailing worn by attorney-at-law Deborah Newland at the Jamaica Chamber of Commerce Grand Charity Ball held at the Jamaica Pegasus Hotel in November, impressed our lens.

Debra Taylor

Select Brands marketing manager Debra Taylor caught our attention in this one-strapped gown with green tropical print and shoulder accents for the Jamaica Chamber of Commerce Charity Ball in November at the Jamaica Pegasus Hotel.

Desiree Depass

Checking out her reflection in a mirror in Devon House's master bedroom, Miss Jamaica World 1999 Desiree Depass wears a Badgley Mischka cobalt gown with an embellished halter-top from Flirt Boutique. Depass appeared alongside 10 other former beauty queens and models in a fashion editorial shot at the historic Devon House for SO in September.

Erroleen & Sophia

The fabulous Erroleen Anderson-Powell (left) and Sophia Max-Brown both gave us another reason to genuflect when we saw them at the Alice in Wonderland-themed Hanover Charities Sugar Cane Ball 2011 at Round Hill Hotel & Villas last February.


Rapper Eve hit the pink carpet at the EME Awards last March at the East Lawn of Devon House in this sleeveless sheath column minidress.

Gavin Douglas

Pulse supermodel Jeneil Williams strutted the runway at last June's Caribbean Fashion Week at the National Indoor Sports Centre wearing a fab yellow draped design by Gavin Douglas.

Grace Silvera

Grace Silvera, LIME's regional VP for marketing and communications, stunned in an Escada gown on the red carpet of the Jamaica Observer Business Leader 2010 Awards hosted at the Jamaica Pegasus Hotel last November.

Ivana Trump

Ivana Trump styled in Dior and Swarovski jewellery from the House of Ivana at her birthday dinner celebrations at Hanover Grange, Tryall last February.

Jaime Stewart-McConnell

Happy Baby distributor Jaime Stewart-McConnell rocked a one-should print mini for the Montego Bay launch of Jamaica OBSERVER CELEBRATES FASHION'S NIGHT OUT last August at Denny Chandiram and wife Veena's Second City home.

Jaunel & Gaye

Smoking hot in white in last July's edition of Essence magazine were Gaye McDonald (left) who wore an Altuzarra Akra jacket and Byblos wide-leg pants, and Jaunel McKenzie, dressed in a Hakaan dress with Wendy Stevens Paris purse.

Judith Haughton

A stunning Indian textile-inspired gown was the choice of attorney-at-law Judith Haughton who accessorised with a coral clutch for the Jamaica Chamber of Commerce Grand Charity Ball last November at the Jamaica Pegasus Hotel.

Juliette & Maya

The style-savvy duo of Julan fashion designer Juliette Dyke (left) and 'it' girl Maya Deer were visible from all angles with their eye-popping fascinators at the launch of Saint International's Style Week Jamaica last May.

Kay Osbourne

TVJ's general manager Kay Osbourne dubbed this outfit her 'Page 2 dress' after rocking it a third time at the launch of The Ity & Fancy Cat Show last July. We spotted Kay twice before in the famous blue dress at Digicel's 10th anniversary celebratrions last April at the Old Coal Wharf, Port Royal and Supreme Ventures' 10th anniversary celebrations at the Jamaica Pegasus Hotel last June.

Kimberley Mais-Issa

Former top model Kimberley Mais-Issa was hot to trot in a Mikael Aghai fuchsia chiffon gown from Flirt Boutique for a SO photo call at Devon House with former beauty queens and models.


Fabulocrats Krystal Chong, Jodi Stewart and Traci Stewart epitomised va-va-voom at the Global Party last September at Fiction Lounge.

Lady Saw

Dancehall diva Lady Saw got the style nod when she wore this sizzling Tadashi gown (complementing it with quirky spectacles) to the EME Awards at Devon House last March.

Maurice Taylor

Dr Maurice Taylor kept it classic cool in a grey blazer, black trousers and loafers, pulling the outfit together with a scarf, at Fiction Lounge's third anniversary last month.


A barefooted Romae Gordon, Pulse general manager, was ethereal in an off-white Meiling design, at Caribbean Fashion Week back in June.

Michelle Parker

Attorney-at-law Michelle Parker styled in a single-strapped cocktail dress, accented with a feather at the waist at her 40th birthday party last April.

Mike Henry

He might have lost his transport and works ministerial portfolio, but Mike Henry's fashion sense is still intact, as was evident at Jean Anderson-Wright's 70th birthday party November last.

Natini Tewani

Natini Tewani turned heads in this red Hervé Leger column gown at the American Friends of Jamaica's 30th Annual Hummingbird Gala at the Capitale in NYC last November.

Nesha and alessandra

Wisynco brand events coordinator Nesha Smith (left) and cousin/fashion publicist Alessandra Bell styled effortlessly in floral maxis at The Global Party at Fiction Lounge last September.

Nordia Witter

Singer Nordia Witter was leggy and fab as a Playboy Bunny at Ficton Lounge's Halloween-themed paranormal party last October.


Saint International model Ornelia Edwards strutted the runway for designer Elie Tahari at New York Fashion Week September last in this golden, empire waist dress.

Paula Kerr-Jarrett

Montego Bay maven-cum-politician Paula Kerr-Jarrett was a study in perfection as she styled in this asymmetrical crimson gown, a nod to the Queen of Hearts at the Alice in Wonderland-themed Sugar Cane Ball 2011 last February at Round Hill Hotel & Villas.

Avery Johnson

New Jersey Nets head coach Avery Johnson and wife Cassandra made a fashionable pair when SO snapped the two at the Kentucky Derby last May.

Racquel Jenkins Moss-Solomon

Style maven Racquel Jenkins Moss-Solomon, principal of Permanent Cosmetics, dazzled (as usual) in her Meiling ensemble at the Kingston launch of Jamaica OBSERVER CELEBRATES FASHION'S NIGHT OUT at the Fiction Lounge last July.

Rosa Joseph

A figure-hugging bejewelled gown was the stylish choice of Pablo's managing director Rosa Joseph for the Jamaica Chamber of Commerce Grand Charity Ball last November at the Jamaica Pegasus Hotel.

Roy Reid

Roy Reid, manager, client portfolios and investment strategies at Jamaica Money Market Brokers, was dapper in a custom-made metallic Spokes Apparel suit with Kenneth Cole tie and shoes at the Jamaica Observer Business Leader 2010 Awards last November held at the Jamaica Pegasus Hotel.


A sophisticated Sedene Blake (from Pulse model agency) appeared between the pages of the September issue of Essence magazine, looking red-carpet worthy in a green Blumarine gown, Olga Prieto brass choker and Valentino sandals.


Fast-rising Saint International model Shena Moulton was a favourite of designers at last September's New York Fashion Week and Paris Fashion Week last October. In the Big Apple, she walked for Tadashi Shoji and in the City of Lights for Paco Rabbane.


Looking every bit the fashionista in her self-designed black and white minidress, Mission Catwalk's season-one winner Shenna Carby lived up to her fashion mantra of "go hard or go home" at the announcement party of the show's winner at the Spanish Court Hotel last June.

Shevolee Bell

Model Shevolee Bell, wearing a Reem Acra gown, sits comfy (and stylishly) in the trunk of the Range Rover Evoque which was unveiled at the Ocean Style fashion showcase last November at ATL Autohaus in Bogue, Montego Bay.


It was history in the making when the 145-year-old Spoerry 1866 unveiled their deluxe men's wear collection for the first time outside of Europe at Caribbean Fashion Week last June. Pulse model Kahil Marks was GQ-ready in this Spoerry ensemble as he walked the runway.

Stacy Anderson

Stacy Anderson wore this avian-inspired winning Avant Garde design by HOD at Saint International's Fashion Block last June.


Terian Cunningham wowed in a lavender M&M gown paired with Badgley Mischka heels at the second anniversary celebrations of her Gabriella's Cosmetics and Gabriella's Couture stores, on the East Lawn of Devon House September last.

Timeka Marsha & Tessane

Guyana's answer to Rihanna, Timeka Marshall (left) oozed mod-glam in a daring minidress, piped with leopard and sequins, alongside Tessanne Chin, who showed off her svelte new figure in an LBD at the CaribFest Awards last January in Barbados.

Tshani Jaja

Tshani Jaja, Digicel brand marketing and communications manager, was a glamourpuss in a printed gown by designer Sequoia at the Jamaica Observer Business Leader 2010 Awards November last at Jamaica Pegasus Hotel.

Ulian, John, Tracy

Our lens caught sight of this smart teal suit, worn by a polished John Small, who appeared the centre of attention for belles Uliana Afanasenko (left) and Tracy Moses at the Smirnoff Xclusive New Year's soirée last January.

Violet Lewis

Hanover Charities co-chair Violet Lewis added sparkly glam in this costume, a chic take on the Queen of Hearts look at the Sugar Cane Ball 2011 at Round Hill Hotel & Villas last February.

Wayne & Sandy

SO's lens snapped Let's Make A Deal host Wayne Brady and Sandra Denton (of Salt 'N Pepa) in their race-day best (hats and all) at the Kentucky Derby in the US last May.

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