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Evening Standard
Evening Standard
Lifestyle
Tania Leslau

Best first-date outfits for women, from classy to more casual styles to suit any occasion

No matter how many times you've done it, a first date is always nerve-wracking.

Feeling comfortable and confident is essential to putting your best foot forward - and that begins with your outfit. Dressing to impress is all very well, but if you’re not feeling comfortable in your own clothes, you’re bound to feel on edge and that is bound to shine through.

There are a few factors to consider before choosing your date night look. Firstly, this is the time to flaunt your personality. You want to wear something that shows who you are, be it with a sprinkling of sparkle, a playful graphic print or a timeless neutral colourway. Clothing can convey confidence. Use it wisely. 

The second element to take into careful consideration is what activity you’ll be doing during said date. For example, a moody evening soiree spent lounging in a wine bar calls for an entirely different aesthetic to a Sunday pub roast and walk. The same goes for accessories and footwear. Never underestimate the power of a great heel and its ability to take your date night attire to new heights.

(Instagram/Nicola Peltz Beckham)

Nobody understands this theory better than the expansive realm of celebrity WAGS. Victoria Beckham, Hailey Bieber, Sofia Richie Grainge and Nicola Peltz Beckham are just a handful of famous faces who have mastered the art of date night dressing. For Amal Clooney, the modus operandi is typically an elegantly draped dress, while Kaia Gerber prefers a classic waistcoat to suit the simmering Los Angeles climate. 

We also have the Hollywood effect to thank for romantic regalia inspiration. Meet cutes are a defining factor of the romance genre, with make-or-break first dates following shortly after. From Kate Hudson’s iconic lemon yellow satin number in How To Lose A Guy In 10 Days to Emma Stone’s coral concoction in La La Land, an epic date night look is bound to help love blossom. 

(La La Land)

Once you’ve got a plan in the works, it’s time to dress accordingly. Discover the best first-date looks to suit any occasion and browse the edit below.

Shop now

Reformation Nadene Dress

Best for: cocktail bar dates

Command attention in a sequined mini dress of dreams. Reformation is the go-to destination for party-girl glamour and the brand’s Nadene Dress is set to get you on the dance floor with a Negroni in hand.

Buy now £258.00, Reformation

Cos Tailored Black Bustier

Best for: wine bar dates

Wine bars require demure, sophisticated looks. Cos’ tailored waistcoat treads the perfect line between classy and cool, thanks to its sculpting construction, button-down detailing and midnight black hue.

Buy now £110.00, Cos

Mango High-Waist Wide Leg Jeans

Best for: Sunday pub dates

Afternoons spent tucked up in a cosy pub corner call for a great pair of jeans. Mango reigns supreme when it comes to affordable denim, and these mid-wash slacks can be paired with any top in your transitional wardrobe.

Buy now £35.99, Mango

Shushu/Tong Corset Velvet Mini Dress

Best for: fancy restaurant dates

Posh dining dates require a traffic-stopping look with a dash of timelessness. Shushu/Tong's corseted dress comes complete with a romantic sweetheart halter neck in a sumptuous ebony velvet.

Buy now £580.00, Matches

Ganni Harlequin Wool Mix

Best for: park dates

Ganni’s Harlequin Wool knit is replete with character. Layer under a classic beige trend, a white tee and jeans for a Scandi It-girl aesthetic as you map Victoria Park.

Buy now £225.00, END.

Cos Panelled Flared Denim Skirt

Best for: coffee dates

Flared silhouettes are undeniably flirty. Cos’ denim skirt doubles up as a date night and day piece. For cute coffee mornings together, team yours with a mohair knit or high-neck top.

Buy now £85.00, Cos

Reiss Frankie Relaxed Denim Jumpsuit

Best for: walking along South Bank

When the sun is shining, nothing tops a meander down the South Bank. Pop into a river-side cafe, head to the National Theatre or enjoy a cheeky tipple wearing Reiss’ Western-style denim jumpsuit.

Buy now £238.00, Reiss

Claudie Pierlot Ecru Sailor Collar Top

Best for: boat dates

The only option for a boat day date, a sailor collar top is a subtle yet stylish way to tap into the nautical-themed affair. Slip into some blue jeans plus a pair of practical trainers and get ready to hoist the sails.

Buy now £139.50, Claudie Pierlot

Stine Goya Noa Checked Jacquard-Knit Vest

Best for: board game cafe dates

An apt pick for playing chess, Stine Goya’s pink and cream checkerboard knit is a tongue-in-cheek take on date dressing. At 70 per cent off, this youthful knit is hard to resist and effortlessly upgrades the current sweater vest obsession with a flirtatious colourway.

Buy now £57.00, Coggles

Chopova Lowena Sexy Mermaid Top

Best for: gallery dates

Dress for the occasion with a sketch-like graphic top by Chopova Lowena. It features a rapidly drawn siren in pink and green tones, ready to lure potential lovers.

Buy now £114.00, SSENSE

Aligne Jamison Denim Trench Coat

Best for: Columbia road dates 

Every weekend without fail, influencers and East London It-girls flock to Columbia Road. Stand out from the crowd with a denim trench coat that you'll wear time and time again. 

Buy now £249.00, Aligne

Mango Checkered Zipper Cardigan

Best for: movie dates

Movie nights call for outfits that prioritise comfort. But that doesn't mean style is out of the equation. Mango’s checkered cardigan in shades of forest green and cream is soft and chic in equal measure for prime cinema snuggling.  

Buy now £44.99, Mango

Adidas Jacquard Long Sleeve Top

Best for: sporty dates

Assert your sporty style authority with a helping hand from Adidas. The brand is a hub of technical, trend-led sportswear pieces, whether you're playing or watching pitchside.

Buy now £25.00, Adidas

Sandro Rhinestone Jeans

Best for: ice skating dates

Finding the perfect pair of jeans is a feat. So when the right pair appears, you don’t hang about. Sandro’s rhinestone jeans will dazzle against the ice and offer a comfortable piece punctuated with sparkle.

Buy now £174.30, Sandro

Siedres Desta Crystal-embellished Sheer Top

Best for: festival dates

Enjoy a grand 75 per cent of this resplendent lemon-yellow Siedres top which is peppered with glistening crystals. With an original RRP of £240, you’ll be bagging yourself a bargain for your upcoming Glastonbury meetup.

Buy now £61.00, Farfetch

Rouje Alexa Top

Best for: at-home dates

At-home dates are deceptively hard to dress for. You don’t want to get too dolled up, but also don’t want to appear overly laid-back. Reach for your favourite pair of jeans and Rouje’s romantic Alexa top in a delightfully soft ribbed jersey with rosebud detailing.

Buy now £60.00, Rouje

Rixo Lena Dress

Best for: casino night dates

Amp up the Bond Girl glamour with Rixo’s Lena Dress. A feathered trim takes this sultry LBD to a whole new level. Adorn yourself with some silver jewels and a petite evening bag and hit the roulette table.

Buy now £245.00, Rixo

Damson Madder Romilda Striped Cotton Blouse

Best for: picnic dates

A romantic gingham or striped blouse is a must for intimate picnic dates. Damson Madder has nailed the dreamy girl aesthetic, and the Romilda Blouse offers a covetable blend of feminine and flirtatious.

Buy now £85.00, Harvey Nichols

Fiorucci Sticker Print Dress

Best for: funfair/carnival dates

Inject colour with Fiorucci’s kaleidoscopic Sticker Print Dress added to your online shopping basket. Iconic sticker prints from the brand’s archive pepper the mini silhouette, which can be worn as it is in summer or layered over a black turtleneck and tights during the chillier months.

Buy now £105.00, Fiorucci

H&M Pinstripe Shirt

Best for: foodie dates

Foodie dates are always fun, so feel at ease in your own skin when slipping into this pinstripe shirt that showcases a loose silhouette and a nonchalant print.

Buy now £44.99, H&M

16Arlington Nage Print Sequinned Tulle Top

Best for: gig dates

Take a leaf out of front-row regulars with 16Arlington’s tulle sequin top. A grunge palette of oyster, burnt orange, ash and mustard makes for a mood, gig-ready ensemble.

Buy now £460.00, Net-A-Porter

Salomon XT-6 Trainers

Best for: tourist-in-your-own-city dates

Walking dates call for a low-key look of your choice. The main priority? Footwear. There’s no quicker way to ruin a walking date by wearing the wrong shoes. Salomon’s XT-6 sneakers are hot property among street style enthusiasts and carefully cushion the foot.

Buy now £159.00, END.

Miaou Elektra Mini Skirt

Best for: aquarium dates

Mini skirts are a failproof date option thanks to their cheeky nature. Miaou’s number goes one step further, depicting a glimmering seawater print to match the tropical tanks of the aquarium in question.

Buy now £90.00, END.

Superdry Faux Fur Lined Longline Afghan Coat

Best for: thrifting dates

Whether heading to Portobello or Brick Lane, an afghan coat will allow your inner Penny Lane to shine. Superdry’s chocolate rendition is a Seventies-inspired statement piece for fashion followers.

Buy now £144.99, Superdry

Kitri Greta Navy Star Lurex Knit Mini Dress

Best for: roller disco dates

Kitri’s celestial mini is sure to inject some Seventies style into your wardrobe. Retro metallic stars pepper the party piece which features a scoop neck and bell sleeves. 

Buy now £140.00, Kitri

Barbour x GANNI Waxed-Cotton Bomber Jacket

Best for: countryside dates

Enjoy a countryside sojourn in Barbour. The brand offers classic field-chic pieces of all prices, but we especially enjoy the label’s Ganni collaboration. Mud à la mode.

Buy now £475.00, Coggles

Whistles Hai Velvet Sienna Dress

Best for: candlelit dinner dates

A plush chocolate dress is the perfect blend of classy and cool. Whistles’ velvet offering is a simple pick which exudes after-hours elegance.

Buy now £208.00, Whistles

Jaded London Film Print Mesh T-Shirt

Best for: arcade dates 

Battle it out against your prospective partner in Peckham's Four Quarters. An inherently fun date to show off your competitive side, an arcade destination calls for a punkish look brimming with playful pigments. 

Buy now £40.00, Jaded London

Topshop Sequin Cami Dress

Best for: burlesque dates

Razzle dazzle them with a sequinned number in a striking shade of crimson red. Topshop's midi dress is a true show-stopper. Pair yours with some kitten heels and a discreet evening bag.

Buy now £50.00, ASOS

Alo Wild Thing Bra

Best for: gym dates

Accentuate your assets while working out. Alo’s Wild Thing bra hugs the form while sculpting the figure. Made from buttery soft materials with ruched detailing, the piece will instantly hone your gym bunny aesthetic.

Buy now £70.00, Alo

& Other Stories Single-Breasted Waistcoat

Best for: post-work dates

Stuck in the office before a date? Dress for both occasions with some impeccable tailoring. Layer this waistcoat over a plain white baby tee and under a coordinating black blazer. Top it off with some chunky gold jewels.

Buy now £75.00, & Other Stories

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