Whether you’re deep in the dating apps, newly coupled, or years into a relationship, one thing remains constant: choosing a date night outfit can feel oddly high-stakes—especially when it comes to Valentine’s Day. You want to look effortless but chic, put-together and polished, but without ever looking overdone—and, above all, like the best, most confident and fabulous version of yourself.
Over time, I’ve learned that having a few simple yet reliable outfit formulas on standby makes all the difference. For me, it’s usually the classic “jeans and a nice top” combination for that perfect high-low look that’s rarely out of place, with different accessories depending on the occasion and setting. And for when the vibe calls for something more elevated? I love the sultry after-dark vibes of a tailored suit worn with heels and a sheer lace bodysuit beneath.
You see, the secret to great date night dressing isn’t reinventing your style—it’s simply refining it. The best looks are ones that feel authentic, flattering, comfortable and quietly confidence-boosting, without trying too hard. And yes, it’s entirely achievable.
To prove it, I’ve turned to some of my favourite fashion insiders for inspiration. Each of the below looks is perfect for Valentine’s Day, but also easily translatable to all manner of date nights, be it drinks, dinner, or wherever the evening takes you…
Lace Slip Dress + Faux Fur Coat
Lean into the romantic boudoir vibes with a silky lace-trim slip dress, a glamorous faux-fur coat, heels and sparkly earrings à la Amalie Gassmann. Being a little on the naughty, naked side is all part of the appeal, but you can also make the look more PG by adding sheer tights and a black cashmere cardi loosely buttoned over the top.
Ducie London
Betty Faux Fur Coat
Swedish Stockings
Beata Seamless Tights
JUDE
Date cutout leather mules
Self-Portrait
Crystal-embellished earrings
Jeans + A Nice Top
A classic outfit formula for a reason, and still one of the best in my experience. Why? Because it nails that high-low look perfectly, offering polish and effortlessness all at once, while being appropriate in most date-night contexts without looking like you’ve tried too hard. My hot tip? Balance out a more elegant top with dark straight-leg denim and kitten-heel boots.
Simkhai
Scarlett caped satin top
AGOLDE
’90s Pinch Waist high-rise straight-leg jeans
COS
Sculpted Brushed Cuff
Reformation
Robbie Ankle Boot
RIXO
Zenni Beaded Bucket Bag in Silver
Little Red Dress
Forget the LBD: come Valentine’s Day, it’s all about the little red dress, as Nina Sandbech knows all too well. It’s fun, flirty, sultry and impactful at the same time, especially if you add matching shoes—while an oversize funnel-neck leather jacket adds the perfect amount of insouciant, casual cool.
Khaite
Daria satin-crepe turtleneck mini dress
ROHE
Leather bomber jacket
Massimo Dutti
Medium-Sized Earrings With Pleats
H&M
Bow-detail satin court shoes
Cosy, Comfy + Chic
It’s important to prioritise comfort when it comes to date-night dressing—that’s when you can really relax and enjoy yourself, in my opinion—all while still looking chic, of course. To achieve this, I usually opt for head-to-toe black, sparkly jewellery and a smart flat over a heel. This Manière De Voir faux fur-trim jacket is my latest discovery, and perfect for the occasion (especially when worn with nothing underneath…).
Manière De Voir
Lina Faux Fur-Trim Black Jacket
Heavenly London
The Mossianite Graduated Collar
Silk Skirt + Cardi
Silk and soft knits are a match made in fashion heaven, and given their sensual textures, a great option for date-night too. Add a pop of pink to lean into your feminine side, and allude to the Valentine’s Day romance of it all too.
Bernadette
Cable-Knit Embellished Cardigan
Arket
Pony-Hair Effect Leather Pumps
Alaïa
Le Coeur Leather Shoulder Bag
After-Dark Tailoring
For a more formal event, sharp tailoring is always a safe bet—but leaving it slightly unbuttoned to reveal a sheer lacy bodysuit beneath will make it date-night ready in more ways than one…
Reiss
Double-Breasted Suit Blazer in Berry
Reiss
Wide-Leg Suit Trousers in Berry
ZARA
Lace Backless Bodysuit
Reformation
Clementine Heeled Mule Sandal
& Other Stories
Chunky Chain Link Necklace
