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5 Date Night Outfit Ideas: Stylists Share Fashion Advice for Every Kind of Date
Stylists reveal essential fashion guidance for every type of date, whatever your plans might be.
Lara Owen Thursday 29 January 2026 08:00 GMT
There's a peculiar pressure attached to getting dressed for a date. Whether it's a first meeting or a long-standing relationship, the outfit can feel more important than the conversation you're about to have. As stylist Angela Kyte explains, "the goal is to look put-together but still like yourself." That fundamental principle holds true across every kind of plan, from candlelit dinners to escape rooms and everything in between.
So, if you're wracking your brain about what to wear for your next date, here are five comprehensive outfit ideas for all occasions, arriving just in time for Valentine's Day celebrations.
1. The Fancy Dinner Outfit
For an evening at a nice restaurant, the brief tends to be chic without seeming too try-hard. Kyte's advice is to keep things elevated but comfortably yourself. "Something I choose frequently is a silky blouse or a well-cut top with tailored trousers or a midi skirt as it instantly looks elevated without feeling overdressed," she reveals.
If dresses are more your preference, she suggests going for "a simple slip dress with a great jacket," adding a smart bag and jewellery to transition the look from day to night seamlessly.
Francesca Zedda, head of womenswear creative styling at M&S, agrees that the dress remains the most instinctive choice for this kind of sophisticated date. "A midi column dress worn with knee-high boots can make for a chic, winter-ready combination," she says, "accessorise with chunky gold jewellery and a clutch bag to elevate the look further."
For those who prefer tailoring, she suggests a structured co-ord, like a jacket and skirt set with a tapered waist that creates a polished silhouette.
2. The Cinema or Cosy Evening Attire
Here, comfort takes precedence – but it needn't come at the expense of style. Zedda frames this approach as "elevated comfort." Her starting point is "a cashmere knit," paired with "wide-leg trousers in velour or pure cotton." The look remains relaxed, but the luxurious fabrics make it smart enough to appear as though you've made a genuine effort.
Kyte recommends leaning into soft materials that are simultaneously luxurious and comfortable. "I adore a soft knit paired with straight-leg jeans or a relaxed midi skirt, layered with a lightweight coat because cinemas are always freezing," she advises.
Trainers or Ugg-like boots represent excellent options for a cosy date, while a crossbody bag leaves your hands free for popcorn or drinks and doesn't take up excessive space under your seat.
3. Casual Drinks Ensemble
This represents the territory of effortless style and perhaps a look that feels closest to your everyday aesthetic. Kyte's formula is reassuringly simple – "a great pair of jeans with a flattering top always works, especially if the top has a bit of texture or an interesting neckline."
Layer with a leather jacket, blazer or statement cardigan to pull the look together cohesively. Shoes perform the most work here; ankle boots, loafers or a low heel can all change the tone dramatically, depending on how you want the evening to feel.
Zedda's contemporary update on the classic 'jeans and a nice top' formula is to choose a romantic blouse or something with subtle detailing, like puffed sleeves, "satin, lace inserts or soft ruffles for contrast" – and finish with ankle boots. It's a combination that feels relaxed but not overly casual.
4. The Daytime Date That Turns Into Evening
Coffee that becomes dinner, a museum visit that drifts into drinks – these spontaneous dates require tactical dressing strategies. For Kyte, the hero piece is "a great jacket or blazer. You can wear it casually during the day over a tee or knit, then in the evening simply swap your bag and shoes, add a bold lip or earrings and suddenly the whole outfit feels elevated."
It's about building flexibility into your look with one key piece to do the heavy lifting. Zedda emphasizes that a statement coat is by far the most important element in your outfit, particularly during winter months.
"Dates, especially first dates, are all about initial impressions," she explains, "whether you arrive in a wool coat, a car coat with contrast sleeves or a blazer with a cinched waist, choose something that makes a statement while keeping you warm."
The beauty of outerwear is that it sets the tone before anything else is revealed, creating that crucial first impression.
5. The Activity Date Attire
Bowling, mini golf, escape rooms – these types of dates are undeniably fun but demand movement and practicality, which shouldn't mean surrendering style entirely. Zedda says footwear is absolutely foundational. "Begin with a pair of trainers in a retro silhouette and work your way up," she recommends, noting the vintage plimsoll is currently trending. "If trainers feel too casual, how about a pair of sleek-yet-sporty Mary Jane pumps?"
Barrel jeans, she suggests, balance these styles well, and softened with "a lightweight cardigan on top," the ensemble becomes practical but still pretty.
Kyte similarly recommends "stretchy jeans or relaxed trousers with a fitted top that won't get in the way," layered with a denim jacket or bomber, to nod to the recent return of 2016 fashion trends.
"Trainers are usually the smartest choice because you'll be on your feet and moving around constantly." Accessories should remain minimal, she advises, so long swinging necklaces and heavy bangles should probably be left on your dresser for more stationary occasions.
