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STYLE | Fashion | Trends & Tips

5 V-Day outfit ideas you can wear from work to date night

As Valentine’s Day approaches, we curated 5 outfit ideas that are sweet, romantic and sexy

By Michelle Yeoh - 

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I recall a rather mortifying event one Valentine’s Day. Having just left the office on my way to meet a date, I had my “go out heels” in a bag on hand in an attempt to delay the inevitable torment that is switching out my comfy flats for pinching stilettos. It probably didn’t help that it was pouring heavily – and I vividly recall the struggle of having to balance on one foot while I awkwardly slip each side into the heels before the date started. I wish that was all there is to the story, but an hour before that, I was in the washroom at the office changing into an outfit that wouldn’t have been appropriate for the workplace.

That’s the thing about date nights: they’re an absolute pain in the neck when they fall on work days. 

I made a solemn vow that night to never put myself through that hullabaloo again. Instead, I need to strategically plan my outfits so that they work for both the boardroom and an after hours date at a fancy restaurant. 

Now that V-Day (and the anniversary of that tragic night) is fast approaching, this ongoing goal of mine feels particularly relevant. The days of hauling a separate outfit and a change of shoes to work are no more; coordinate an outfit that hits the sartorial nail on the head from desk to drinks.

 To help you with that, here are 5 curated ensembles to try out this V-Day below.

Romantic vibes

Credit: Matchesfashion
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Emilia Wickstead Jules cropped sweetheart-neck cloqué top, S$680; Oséree Lumiere lame wrap skirt, S$320, Proenza Schouler square-toe leather sandals, S$770; Rosantica Baby Heart mini crystal-embellished bag, S$510; Maryjane Claverol Katia double-hoop earrings, S$235; all from from Matchesfashion

Emilia Wickstead’s cream cropped top with a sweetheart-neckline manages to look impeccably romantic with a subtle innocence, and sophisticated at the same time.

For V-Day 2020, team this top with a relaxed wrap skirt in glittering pink for a pop of colour. Coordinate the look with minimalist square-toe strappy sandals in red, an occasion-fitting heart-shaped bag bedecked in crystals, and contemporary hoop earrings with an artful finish.

Contemporary neutrals

Credit: Net-a-Porter; Matchesfashion, Mytheresa
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Loewe cropped tie-detailed wool and cashmere-blend sweater, US$1,150 (S$1,569.61)  from Net-a-Porter; Wandler Isa square open-toe python-effect leather mules, S$490 from Matchesfashion; Mara Hoffman + NET SUSTAIN Lolita knotted tiger-print organic cotton maxi dress, US$371.01 from Net-a-Porter; Jacquie Aiche fishtail 14kt rose-gold drop earrings, S$2,129 from Mytheresa; Lauren Manoogian New Grid wool tote, US$231.32 from Net-a-Porter

A sexy slip dress is the first thing we all love to reach for when it comes to special date nights. To render it appropriate for the office, try layering a cropped sweater on top of the slip dress. Loewe’s uber-cropped number makes for a chic option with a tongue-in-cheek twist.

Finish the look with baby pink python-effect mules, matching rose gold earrings and a woven wool tote bag.

Whimsical energy

Credit: Luisaviaroma, Farfetch, Net-a-Porter, Mytheresa
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Nina Kastens Mop face earrings w/ mother of pearls, S$504 from Luisaviaroma; Simon Miller buckle strap sandals, US$704 from Farfetch; Marni two-tone tied sleeves dress, US$1,422 from Farfetch; Lele Sadoughi stacked stone barrette, S$185 from Mytheresa; Prada Fiori leather-trimmed appliquéd nylon tote, US$1,441.62 from Net-a-Porter

For those of you who prefer a fun, quirkier outfit, this ensemble has got you covered. A duo-toned half-half dress from Marni featuring deconstructed shirt sleeves that tie to cinch the waist, a pair of abstract face-shaped earrings, and a floral applique tote bag from Prada – craft the perfect whimsical look this Valentine’s Day with these charming pieces.

Complete your look with platform sandals in a saturated zesty orange and a statement barrette with decorative stones in playful shapes.

Sexy sophisticate

Credit: Net-a-Porter; Matchesfashion
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Roland Mouret Zenna ruffled silk-georgette halterneck camisole, US$685 from Net-a-Porter; Theodora Warre mismatched garnet hoop earrings, S$310 from Matchesfashion; Cushnie silk-charmeuse wide-leg pants, US$925 from Net-a-Porter; Tsatsas Tape XS grained-leather clutch bag, S$735 from Matchesfashion; By Far Theresa leather wedge mules, US$344.37 from Net-a-Porter

Match a deep purple camisole with cascading ruffles together with a silky pair of wide-leg pants in a pearlescent “antique-rose” hue. Balance out the silhouette of the billowy wide legs with the sleek, sharp lines of these minimalist mules by By Far, and go for a burgundy clutch bag to match.

A simple, elegant pair of good hoop earrings featuring a garnet stone in the shape of a heart will elevate this look even further.

Sweet pastels

Credit: Net-a-Porter; Matchesfashion
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Remain Birger Christensen Debbie double-breasted cotton and linen-blend blazer, US$271.39 from Net-a-Porter; Jil Sander Whipstitched square-toe leather ballet flats, S$1,050 from Matchesfashion; Gucci embroidered tulle bodysuit, US$797.22 from Net-a-Porter; Ellery Gulliver crepe midi skirt, US$688.74 from Net-a-Porter; Wandler Georgia croc-effect leather shoulder bag, US$634.93 from Net-a-Porter

Dip a foot in the “relaxed tailoring” trend and opt for an oversized blazer in a pastel sunshine yellow. Team it with a matching midi skirt in the same colour and give the look a sexy V-Day-twist with a soft pink embroidered tulle bodysuit that resembles lacey lingerie.

Throw on these ballet flats from Jil Sander – they look immaculate and dainty, and feature chic metal hoops that act as ankle cuffs. Haul a pink croc-effect shoulder bag to finish the polished look.

ALSO READ: Lucky Colours To Wear In February, According To Your Horoscope

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styling tipsvalentine's daywork wear
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