Deciding what to wear on a date can feel overwhelming, but the right outfit changes everything. From Valentine’s Day dates to first dates, I’ve compiled a handy guide for deciding what to wear.
Getting dressed for a date always comes with a mix of excitement and overthinking, and whether you’re in a long-term relationship or newly dating, the right outfit is a must-have in order to look and feel your best. Personally, I gravitate towards pieces that make me feel comfortable and elegant whilst remaining true to my personal style, as there is nothing worse than feeling overdone or confined by tight or uncomfortable clothes—we’ve all been there! Pairing your existing capsule wardrobe staples with some fresh new picks is the best way forward.
Dressing for a date isn’t about following any rules or formulas, ultimately, it’s about curating a look that makes you feel like the best version of yourself. And of course there may be things to consider in terms of where you’re heading, what you’ll be doing, and what the weather forecast predicts. So our guide considers everything, from daytime and casual dates to Valentine’s Day dinner reservations. We’ve got you covered.
Valentine’s Day Date Outfit
It might seem cliché to wear red on Valentine’s Day, but I simply love it! And what better way to wear it than a satin mini-dress? Red and black pair so well together it’s almost a no-brainer, and there are tonnes of ways you can wear this colour combination, but a dress and a black blazer is an elegant option. Add slingback heels and some gold sparkly earrings.
This long sleeve dress has a loose silhouette that is perfect for wearing all evening long. On cooler days add tights and layer up with a tailored blazer.
H&M Double-breasted blazer
A blazer feels chic, elegant and sophisticated making it a go-to for when considering what to wear on a date. Layer over dresses, blouses or even jeans.
COS Coiled Freshwater Pearl Hoops
If you’re scouting for jewellery COS have some great high-street finds. These earrings feel both glamorous and on-trend, making them perfect for date nights.
Daytime Date Outfit
If you’re heading out for a daytime adventure, pairing the best wide leg jeans with a glamorous blouse is a fail-safe option. A leopard print blouse tucked into high-waisted denim jeans feels laid-back yet elegant, making it ideal for transitioning from day to night. Pair a red leather handbag with leopard for an added touch of vibrancy.
& Other Stories High-Waist Flared Jeans
These high-waisted jeans feel super 70s, yet perfectly on-trend. Team with wedge heels for special occasions or chunky trainers for the ultimate comfort.
Next Animal Print Tie Neck Blouse
Leopard print has had a major resurgence and opting for a blouse is the perfect way to get in on this trend. Style with indigo denim jeans for the perfect date-ready look.
Radley Small Zip-Top Grab
Now discounted, this ‘lava’ red Radley handbag is the ultimate way to add a playful touch to your weekend looks.
Date Night Outfit for Winter
When the temperature drops, it can feel hard to know how to remain glamorous whilst keeping warm; however, opting for cosy, stylish layers is key. A denim dress offers a thick, warm material while still feeling elevated. Add the best knee high boots in suede or leather and finish off the look with a warm coat and thick winter tights.
River Island Indigo Denim Shirt Collar Mini Dress`
This dress offers the perfect floaty relaxed silhouette. Wear through the cooler months with thick tights and knee high boots and in the summer pair with sandals.
H&M Handmade Wool Blend Coat
This might just be one of the best winter coats we’ve spotted this season. Style with almost anything from evening dresses to layered over the chicest trouser suit.
Zara Suede Leather Cowboy Boots
These cowboy boots are at the top of my wishlist. From pairing with midi-dresses to styling with skirts and skinny jeans these are boots are a must-have.
Date Night Outfit for Plus Size Women
When it comes to what makes the best date night outfits for plus size women, there is lots to consider, including what brands to shop from. We’ve opted for a fabulous gathered dress from the excellent Your Curves range at Next and paired it with a buttery yellow cardigan from the ASOS Curve collection. To finish off this vibrant date night outfit is the chicest drawstring handbag from Arket.
Yours Curve Natural London Mesh Gathered Dress
This mesh dress has an on-trend floral print in light yellow and dark brown. It’s long sleeves and gathered waist are sleek and sophisticated, perfect for evenings out.
Arket Stone-Detailed Drawstring Bag
This small white bag is made from quality leather and features the chicest drawstring closure and four colourful decorative stones.
ASOS Curve Buttermilk Cardigan
Opting for a light-weight knitted cardigan on a date is a smart choice if you aren’t sure what the temperature will be like, and this buttermilk colour is simply delightful.
First Date Outfit
First dates are all about projecting your personality whilst wearing something that makes you feel confident and stylish. A simple slip dress and a blazer can balance feeling feminine whilst remaining smart, and the added Mary-Jane flats will keep your feet comfortable all evening long.
Vila Satin Maxi Dress Yellow
This satin max-dress is a showstopper! Layer over the top a white blazer or even a white cardigan and add some on-trend ballet flats or Mary-Janes and minimal gold jewellery.
Nobody’s Child White Single Breasted Blazer
This sleek tailored blazer is the perfect way to add a smart feel to your special occasion looks, whether you layer it over satin dresses or floral prints.
Hush Maeva Mary Jane Leather Flats
Now discounted in the sale, there is no better time to snap up these stylish Mary-Janes. Perfectly in line with the shoe trends of 2025 these flats will pair with anything, from barrel leg jeans to floaty dresses.
Casual Date Night Outfit
If your date night plans are looking more casual than formal, your outfit needs to reflect that. Opt for a floaty printed dress that looks effortlessly chic and layer over a stylish black leather jacket. For an elegant finishing touch, add some suede heeled ankle boots.
M&S Round Neck Spot Print Midaxi Tea Dress
This delightful spotted dress is one of M&S’s best selling pieces. Style with chocolate brown suede boots and layer over a black leather jacket for an elevated, casual feel.
Mango Leather Biker Jacket
A cropped leather jacket is a fail-safe piece of outerwear for when you want to look put together but effortless. Style yours with anything, from special occasionwear to your weekend denim looks.
Next Forever Comfort Leather Western Boots
These boots have a western-style and come in the chicest chocolate brown colour. The block heel offers just the right amount of height without the discomfort of a stiletto.
Dinner Date Night Outfit
If you’re heading out for dinner the chances are you want to feel put-together and polished, that’s why you can’t go wrong with a midi-skirt and slingback heel combination. Add a boho-inspired ruffle blouse and some gold statement earrings and you’re good to go.
Zara Tie Front Ruffled Top
This ruffled blouse is already on my wishlist. In a trending chocolate brown shade and featuring dramatic flared sleeves this piece feels like a staple that you can wear on repeat.
H&M Slit Hem Pencil Skirt
A pencil skirt is the ultimate go-to if you’re not sure what to wear on a date and styled with a floaty ruffled blouse and slingback heels you’re good to go.
Charles & Keith Pointed-Toe Kitten-Heel Slingbacks
In an on-trend faux-suede material these slingback heels will become your wardrobe go-to. Pair with denim jeans, midi-skirts or flowy dresses.
FAQs
What is the best thing to wear on a first date?
Our 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. 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.
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