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.
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.
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.
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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
