It’s February, which means Valentine’s Day is around the corner. If you’re on the hunt for the perfect date-night outfit, I’m here to help. Whether it’s a first date, a casual coffee, or a special anniversary dinner, my handy guide will see you through a variety of date scenarios, from at-home dates to dining out.
Getting dressed for a date always comes with a mix of excitement and overthinking, and whether you’re in a long-term relationship or new to dating, the right outfit is a must to look and feel your best. I always recommend choosing pieces that you’re comfortable in, that embrace your personal style, as there is nothing worse than feeling overdone or confined by tight or uncomfortable clothes. And teaming existing winter capsule wardrobe staples with some fresh new-in styles is the best way forward.
1. Valentine’s Day Date Night Outfit
Of course, it’s best to consider the dress code of where you’re heading if you’re planning a Valentine’s Day outing, but for a special dinner out, the theatre or an evening occasion, maxi or midi dresses paired with a lightweight blazer work seamlessly. It might be a little bit cliché to wear red on Valentine’s Day, but it’s also a colour associated with romance – and fire engine red is one of the key spring/summer fashion colour trends 2026.
Red and black pair so well together, it’s a no-brainer to consider pairing a red dress with either a black blazer or a lightweight cardigan; however, there are a variety of ways you can wear this colour combination.
Finery London
Polka Dot Midi Tea Dress
The empire waist on this polka dot tea dress enhances your shape, whilst the sweet elbow length sleeves add structure to this design. On cooler days, add tights and your best knee-high boots to this style.
ZARA
Double-Breasted Oversize Blazer
Layer up with this double-breasted blazer. Tailoring is a go-to staple for layering over dresses, especially when considering what to wear on a date. Outside of date nights, wear this jacket as part of a sleek jeans and a blazer outfit.
M&S
14ct Gold Plated Heart Hoop Earrings
If you’re scouting for affordable jewellery, you don’t have to look too far; M&S have some great offerings this season. These love-heart earrings lean into the romance-filled season, and they are versatile enough to wear every day.
2. Daytime Date Outfit
For a daytime date, the key is striking a balance between feeling comfortable and looking dressed up, too. If you’re planning on being active on your date, such as exploring a gallery or visiting a city, make sure you opt for footwear you feel comfortable in. Ankle boots with a block heel strike the perfect balance between elevated and practical, plus they will offer you extra height without the discomfort of a stiletto.
Denim flared, or your best wide-leg jeans, are great for adding dimension to your silhouette. Pair them with a tucked-in blouse or a neat button-up shirt for a smart-casual finish. This formula can also work as a coffee date outfit.
Zara
Z1975 Wide-Leg Belted Jeans
These belted jeans have a front seam that makes them appear vintage. You could style them with wedges or block-heeled ankle boots if you’re looking to dress them up; alternatively, wear everyday with your most comfortable trainers.
Mint Velvet
Navy Heart Print Chiffon Blouse
This navy blouse features a sweet heart print and ruffled sleeves. Not only does this blouse work for dates, but it can also work if you’re on the hunt for smart casual outfit ideas or for the office or fancy dinner reservations.
Zara
Split Suede Cowboy Ankle Boots
Elevate your current footwear collection with these suede cowboy-boot-inspired boots. The rich brown shade is a versatile choice, and the block heel offers extra height without discomfort.
3. Date Night Outfit for Spring
As we enter spring, your date night outfits will shift with the changing season. Stash away heavy-duty coats and opt for one of the best trench coats, a more appropriate alternative that will combat against spring showers, whilst not being overly warm.
If you’re heading to a venue indoors, like a restaurant or bar, what you wear underneath is equally important. Some sleek, tailored trousers and a lace-trimmed or satin cami-sole will ensure you look great once you’ve arrived at your destination.
What’s great about date night styling when the temperature warms up is that you can opt for open-toe shoes, try adding these mules from Arket to the formula below.
M&S
Cotton Rich Belted Longline Trench Coat
During the spring months, layer this cotton-rich trench coat over your date night outfits. It’s designed with a longline silhouette and a flattering belted waist to cinch in your figure.
Boden
Silk-Blend Lace Trim Cami Top-Black
Already firmly on my spring wishlist, this lace-trimmed camisole is a playful addition to any date night outfit. It’s elevated yet slightly flirty which makes it perfect for the occasion, and the short sleeve design is ideal for when temperatures begin to rise.
Nobodys Child
Black Pleated Wide Leg Trousers
These are the kind of trousers that quickly become the backbone of your wardrobe. The wide-leg design and front pleats makes them an elevated choice whilst the black colour makes them versatile enough to style with almost anything.
4. Coffee Date Outfit
For a coffee date outfit, the goal is to look effortlessly put-together while still feeling confident and well-dressed. A lightweight knitwear piece paired with a satin slip skirt strikes the perfect balance between cosy and elevated. A jumper feels relaxed and approachable, whilst the slip skirt suggests that you’ve made a little effort.
In terms of footwear, midi-skirts pair well with a range of silhouettes; however, we’d suggest wearing flats for a coffee date, Mary-Janes, or ballet flats are an on-trend choice that feel feminine and playful. Or take a look at the spring/summer shoe trends 2026 for more inspiration.
Mint Velvet
Butter Yellow Knit Button Detail Jumper
Butter yellow is an optimistic spring shade. This button detail jumper will make a handy addition to your current rotation, pairing with a range of bottoms, including your favourite denim jeans and silky satin skirts.
Rixo
Kelly Silk Midi Skirt in Leopard Brown
This leopard print midi is a coveted skirt style by the British clothing brand Rixo. It’s made from silk crepe de chine and has a warm brown leopard print, which acts as a neutral – you can style it with a variety of styles of tops.
Sézane
Aubane Low Babies – Natural Woven
If you wanted to try out the Mary-Jane trend, this woven pair are a great place to start. Made in a Portuguese atelier, they feature a smooth leather exterior and a woven textile lining.
5. First Date Outfit
First dates are all about projecting your personality whilst wearing something that makes you feel confident, stylish and most importantly, comfortable. The setting will naturally guide your choice, but the goal should be to wear something authentic to you.
Midi dresses are a fuss-proof option that requires limited styling, something which will minimise nerves when getting dressed for a first date. In terms of footwear, a heeled boot is a chic yet practical choice that will make you feel a little bit elevated without feeling over the top. A top tip is to coordinate your bag and shoe colour or fabric.
Boden
Button Detail Denim Dress-Indigo
This denim tea dress features short puffed sleeves and a cinched belt, which makes it an excellent find if you’re on the hunt for stylish dresses to hide a tummy. Team with your favourite boots, best white trainers or some trusty loafers, the options are endless.
M&S
Suede Kitten Heel Pointed Knee High Boots
Made from real suede leather and coming in a rich brown shade, you’ll be wearing these boots for seasons to come. The supple suede material will make them a luxurious addition to any date night outfit.
DeMellier
The New York Shoulder Mocha Suede & Mocha Smooth
An elongated version of DeMellier’s iconic New York shoulder bag, this style offers an elegant, more compact design that’s perfect for evenings out or special occasions. Choose from four colourways, including burgundy or chalk white.
6. Dinner Date Night Outfit
If you’re heading out for dinner, the chances are you want to feel put-together and polished, but also comfortable too. Nothing quite beats a jeans and a blazer combination, and this go-to formula works for plenty of restaurant settings; however, if you’re going somewhere more exclusive, like a fine-dining restaurant or hotel, you might want to swap out the jeans for tailored trousers or a skirt.
Depending on the venue, you can dress it up or keep it more relaxed, but the mix of tailoring with denim works without trying too hard. A satin blouse is the ultimate base layer to tuck into denim, and looks great layered underneath sharp tailoring. To finish, just add a pair of kitten heels or style with your favourite flats for a more laid-back feel.
ME+EM
Sharp Shoulder Blazer
Investing in a tailored jacket like this striped cinnamon blazer is always a good idea because it can be styled with almost anything. This sharp blazer is part of one of the best trouser suits when paired with the matching trousers.
Mango
Satin Finish Flowy Shirt
From a high-street favourite, this silky white blouse is a staple that you’ll get plenty of wear out of. Tuck into high-waisted denim jeans or pair with sleek, tailored trousers for more formal occasions.
Mint Velvet
Black Wash Straight Jeans
Straight-leg jeans are fail-proof choice if you’re not sure what to wear on a dinner date, and styled with a smart blouse and a blazer, you can transform them from laid-back to date-worthy.
7. Staying-in date night outfit
For a stay-in date night, it’s all in the small details; you want to feel comfortable and a little bit luxurious. Long-sleeve satin pyjamas are perfect because they bring that elevated feel whilst still being soft enough to lounge in. Pair them with some of the best slippers for a warm and comfortable finishing touch, and don’t forget to add jewellery.
Eberjey
Gisele Tencel™ Modal Long Pj Set
This vivid red set from one of the best pyjama brands is made from a buttery soft fabric blend that will keep you warm and cosy. The set features a relaxed long-sleeve top with front buttons and white contrast piping, giving it a classic finish.
Selfridges
Scuffette Ii Slippers
Investing in a pair of UGG slippers is always a good idea. Cosy and inviting, these slippers are finished with a shearling-line interior for maximum warmth, whilst the chesnut suede makes them a stylish choice.
Monica Vinader
Gold Vermeil Pear Diamond Chain Necklace – Lab Grown Diamond
Accessorise your date night outfits with this beautiful diamond chain necklace. It’s made with 18k gold vermeil and a cut lab-grown diamond, set in a pear-drop setting. Buy for yourself or add to your Valentine’s Day gift wishlist.
FAQs
What is the best thing to wear on a first date?
Freelance Fashion Editor Julie Player comments, “When deciding what to wear on a first date, the most important thing is to choose an outfit that you feel reflects your true style personality. A first date is not the time to try out any adventurous new trends. Whether you’re heading for a quick coffee date or spending an evening out, choose an outfit that you feel comfortable and confident in. Having said that, you have one opportunity to make a first impression, so you want to ensure that you are reflecting the best version of yourself.
Later saying “Use colour to boost your confidence, bright and bold shades will project an upbeat aura, or maybe a soft pastel shade will suit you better, try out a few options before the big date, don’t leave the decision making until the last minute. Playful prints or interesting accessories are a great way to project your personality too, and can make a great conversation opener.”
Should you dress up for date night?
In short, yes, dressing up for a date night or day signals that you have put effort and care into your appearance. However, the most important thing is that you are wearing an outfit which you feel comfortable and confident in, whether that’s laid-back denim or a little black dress.
With over 30 years experience in the fashion industry, Julie is a regular contributor to Woman & Home, Woman’s Weekly and Chat magazines, creating engaging fashion and lifestyle content for woman of all ages. She also works in the wardrobe department at ITN, dressing the presenters for Good Morning Britain. In her late fifties, Julie understands what women want when it comes to figure flattering fashion.
