Dressed to Perfection: A Guide to Fabulous Holiday Footwear

The Chrisitan Louboutin ‘Water In Love’ campaign by Peter Lippman for Christian Louboutin S/s 2015, the Senora T- Strap Pumps are shown. Image CHRISTIAN LOUBOUTIN/PETER LIPPMAN

As the holiday season rolls around, many of us will find ourselves with extremely full schedules. Shopping and family events aside, the sheer number of social events that we’re planning to attend can be dizzying (but who’s complaining?). To elegantly navigate the season, us chic gals must prepare our ensembles well in advance and for me, this begins with footwear. Yes girls, this is a shoe post!!

Lupita Nyongo’o is resplendant in Miu Miu’s Crystal- Embellished Sculpted Heel Sandals, by Inez+Vinoodh for Miu Miu’s S/s 2014 campaign. Image MIU MIU/INEZ+VINOODH

My twin island home of Trinidad & Tobago has been long renowned for being the Caribbean’s party center, but this isn’t your regular “Caribbean” social scene- especially during the Holiday season. With social events ranging from glamorous white and black tie events, semi-formal dinners, house parties, club parties, Down-the-Island parties, regattas, Tobago New Year beach parties to pre-Carnival fêtes, your outfits- especially your shoes, have got to be on point for you to make it through all of these in fine style.

Casadei’s Moroccan inspired S/s 2014 campaign by Sebastian Kim. Image CASADEI/SEBASTIAN KIM

By following a few simple rules when choosing your footwear, it’s quite easy to always have the appropriate shoe choice for each event- even if you have a relatively small shoe collection or you’re packing a few pairs into a travel bag (like I’ll be doing). Although a few of the events I listed are exclusively Caribbean, with a little tweaking of the following guidelines, you’ll be able to easily manage all of your holiday footwear needs.

Eva Herzigová wears Brian Atwood’s Zoe Lace Up Sandals for the Brian Atwood S/s 2013 campaign by Mert+Marcus. Image BRIAN ATWOOD/MERT+MARCUS

The golden rule is to pay attention to the anatomy of the shoe and the event’s dress code. For the most part, all types of ladies’ footwear have the same features (there’s a diagram below). The most important ones to pay attention to are the vamp (or toe strap) and the heel, particularly the heel’s thickness. Make sure that the shoe fits and is comfortable for walking, standing and dancing. If the soles are relatively smooth or leather, you might also want to score them a bit so that they’re less prone to slipping on wet or icy grounds.

The anatomy of a shoe, as seen on the Ruthie Davis Emilie Studded Metallic Cage Sandal

As for which style to choose for which event, generally the more formal the get together, the thinner your heel should be- that’s why stilettos are the shoe of choice for galas and red carpets like those at Cannes or the Oscars. This is my general guide- if you’re attending something formal, choose footwear with thin, elegant straps or a covered front and with a reasonable slender heel. For parties, go all out. Bring out those sexy pumps or aerodynamic sky high wedges. Remember that this is the most glamorous time of the year, so now’s the time to wear your embellished shoes! Gorgeous sandals and ballet flats are great for the large cooler parties and fêtes that we Trinis love, but if you’re going to be anywhere warm, these are great for informal events.

Karlina Caune in the Tom Ford Metallic Gold Knee- High Gladiator Sandal, by Tom Ford for the Tom Ford S/s 2013 campaign. Image TOM FORD

Colour wise, it’s always a smart choice to stick to jewel tones, metallics and black or white for formal night events. If you’re attending something semi-formal or during the day, it’s perfectly fine to gravitate towards brighter shades. Patterns and prints are also good for less stuffy affairs and don’t be afraid to experiment with daring shapes and embellishments like beading, bright appliqués and graphic motifs.

Most importantly, make sure that you can properly walk in your heels- even if you have to practice at home for a few days before the event- trust me, no one wants to be remembered for this:

Poor Kamila, we still remember her moment at Vivienne Westwood S/s 2007

I shouldn’t even have to mention this, but I’ve seen this major faux pas committed too many times to let it slide: if you are attending an event on a yacht, a boat or any type of sea-faring vessel, do not wear heels! Apart from the fact that it’s extremely hard to keep your balance in heels on unstable ground, these shoes horribly damage the wooden decks of the vessel you’re traveling on! Also consider the added challenge of walking on the dock in heels (bad if it’s concrete, worse if it’s wood) added to the procedure of boarding the yacht and… it’s really not worth it. Stick to flats. Espadrilles or wedges can also be worn, but only if the platforms are soft- cork and wood covered with fabric or leather are your best bets here.

The Ted Baker London “Tastefully Ted” campaign by Sam Hofman for Ted Baker London S/s 2013, the Pink Escinta Pumps are shown. Image TED BAKER LONDON/SAM HOFMAN

Follow these suggestions and you’ll be able to navigate your season fabulously! I’ve listed some dress code categories for holiday events below, along with some FAB shoe suggestions for all you stylish ladies. Hopefully they’ll help you put your best foot forward this holiday season!

-xx Ana

Daytime Casual

This can be anything from a daytime party at a friend’s house, a low key family gathering, a beach dance… heck even holiday shopping (style bloggers are everywhere). Casual means comfort, so you can wear anything from slingbacks, strappy sandals, slides, mules and cute flats (definitely the flats for the beach). Be bold and experiment with cool shapes and embellishments- bright beading, embroidery or appliqués, neon colours, 3-D florals and crystals are all fun styles to try.

Guiseppe Zanotti Studded Ankle-Wrap Chunky-Heel Sandal, Militare

Ancient Greek Sandals Eyes Triple-Strap Thong Sandal, Natural

Giuseppe Zanotti Leaf Strap Sandal

Kate Spade Alejandra T-Strap Sandal, Luggage

Alexander Wang Kai Contrast Sandal

Alexander McQueen Skull Sandal, Black/Gold

B Brian Atwood Alcarra Flat Sandal

Dolce & Gabbana Polka-dot Canvas and Embroidered Cork Wedge Sandals

Bottega Veneta Woven Leather Thong Sandal, Pale

René Caovilla Chandelier Swarovski Crystal Thong Sandal, Sand/Smoke

Daytime SemiFormal

You can basically wear any type of shoe to these- sandals, peep-toe platforms, pumps, wedges and even dressy flats. Keep it playful and experiment with pretty patterns, cool embellishments and bright colours.

Sophia Webster Lola Metallic Crystal-Toe Pump, Silver

Yves Saint Laurent Jane Ankle Cuff Sandal

Christian Siriano Gold Multi- Color Beaded Pump

Givenchy Floral Print Leather Ankle- Wrap Sandal

Paul Andrew Delphi Metal- Trimmed Leather Wedge Sandals

Charlotte Olympia Flora Leather and Mesh Pumps

Stuart Weitzman Annex Metallic Wedge Sandal, Penny

Christian Louboutin Senora 130mm T-Strap Pump

Daytime Formal

Anything formal requires ladylike footwear, but you can get away with more daring designs at daytime events. Stick to heels regardless of style and you’ll be fine. During the day is the time to wear brighter colours and patterns- florals are especially pretty- you can also get away with bright metallics and punchy embellishments.

Oscar de la Renta Gladia Scalloped Sandal, Carnation

Casadei Blade Denim Pump

Christian Louboutin Pigelle Follies 120 mm Red Sole Pump, Multicolor

Alejandro Ingelmo Flavia d’Orsay Point- Toe Pumps, Black/Metallic

Christan Louboutin Bandy 120 mm Point- Toe Red Sole Pumps

Oscar de la Renta Artha Pointy Suede Mesh Pump, Grey

Sophia Webster Lola Suede Fringe Pump, Tropical Green

Manolo Blhanik BB Fabric Pump, Vivid Floral

Daytime Yachting

This category is twofold: formal events like regattas, luncheons and location weddings, and casual gatherings like a cruise party or a jaunt up the islands.

Formal Yachting

You can get away with wearing wedges or elevated sandals if the soles of the shoe are soft, but for the most part stick to flats. Ballerina flats, mules, luxe sandals and embellished slides are all good for these events, the ‘rules’ of formal dressing are somewhat relaxed on the high seas, so you can get away with wearing shoes with peep- toes and pretty straps.

Christian Louboutin Suspenodo Flocked Glitter- Finished Flats

Jimmy Choo Inka Wedge Mirror Sandal, Gold

Bally Leather Wedge Sandal

Emilio Pucci Silk Wedge Sandal

Seychelles Night & Day Mini Wedge, Copper/Platinum

Jimmy Choo Baxen Glittered Wedge

Elma Pointed Toe T- Strap Flat, Olive Leather

Casual Yachting

Anything casual works, but aim for footwear with non- slip soles.

Melissa Jason Wu Jean Flat, Red

Dolce & Gabbana Magpie Embellished Sandal

Valentino Rockstud PVC Thong Sandal, Poudre

Ivy Kirzhner Taj Mahal Sandal, Gold

Schlutz Christy Wedge Espadrille

Yves Saint Laurent Studded Leather Fringe Sandal, Nero

Valentino Rockstud Chevron Thong Sandal, Multicolor

Prada Patent Logo Wedge Thong Sandal, Rosso

Valentino Multicolor Espadrille Wedge Sandal


Anything goes here- play with wild colours, interesting shapes, cool embellishments and bright (or neon) motifs to your discretion. In the Caribbean, especially Trinidad, Barbados and Jamaica, and warmer seaside spots in Europe, heels are the de rigueur shoes. Wear a pair that’s beautiful and comfortable!

Jimmy Choo Lynthe Mixed- Media Platform Sandal

B Brian Atwood Alouette Wedge Sandal

Christian Louboutin Mandolina Laser- Cut Mesh Bootie, Black/ Gold

Alejandro Ingelmo Odyssey Iridescent Cutout Bootie, Black/ Metallic

Giuseppi Zanotti Suede Strappy Platform Wedge Sandal, Pink

Casadei Platform Peplum Leather Pump, Ecru/ Red

Burberry Virginia Tapestry Peep- Toe Ankle Boots

Fendi Metallic Leather and Suede Sandals

Casadei Venice Suede and Metallic Pumps, Plum

SemiFormal Night

We naturally try to dress a little more elaborately at night, so it’s fine to pull out the glitter after dark. Clubbing aside, heels are a must for night and there are so many fabulous options out there. Peep- toed pumps, platforms, elegant sandals and killer stilettos are just a few choices, and you can get away with glitzy adornments, metallics, rich colours and opulent fabrics.

Christian Louboutin Beauty K Metallic Cage Red Sole Sandal

Valentino Lace Bow Peep- Toe Platform Pump

Ted Baker London Reflective Landscape- Print Satin Pump, Blue

Giuseppe Zanotti Haymitch Sandal

Christian Louboutin Cloo 100 Studded Snake, PVC and Leather Slingback Pumps

Givenchy Monia Leather Sandals with Crystals

Christian Louboutin Pina Spike Red Sole Sandal, Black/ Gold

Kurt Geiger London Maia Bow Sandal

Givenchy Shark Lock Ankle Wrap Sandal, Black

Formal White and Black Tie

Black tie calls for all-out glamour, so when attending these events you can break out all the gorgeous, jewel-encrusted numbers you want. Stick to ladylike closed front shoes and stilettos, sling-backs and kitten- heeled pumps are all ideal. If you absolutely must wear flats (and the only excuse for this is if you actually have a broken leg or a twisted ankle) look for something embellished. Exotic skins and detailed leather are great for a simpler shoe and if you’re wearing something fabric- covered, stick to luxurious materials like silk, velvet, net and lace. Experiment with luxe accents like metallic and iridescent finishes, lush embroidery and adornments like crystals, metal spikes and glimmering beads.

Christian Louboutin Follies Crystal Mesh Red Sole Pump, Silver/ Nude

Jimmy Choo Tania Crystal Degrade Pump, Black

Valentino Rogue Abaolute Sig 100 Diamanté Pump

Manolo Blahnik Hangisi Crystal Buckle Stain Pump, Green

B Brian Atwood Nicolette Pump

Christian Louboutin Follies Spike-Studded Glitter Pump, Gold

Dolce & Gabbana Crystal Embellished Mesh & Leather Slingback

Gina Felicity Satin Flat

Miu Miu Crystal Embellished Calfskin Pump

Manolo Blahnik Swan Pump

Dolce & Gabbana Silver Lining Colletion Belluchi Velvet Pump

Christian Louboutin Viennana Strappy Suede Red Sole Bootie, Black

Tom Ford Python Point- Toe Stiletto Pump, Gold

Gina Whitney Pump

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