Figuring out the perfect date night outfit can feel tricky, whether it's a first date, a casual coffee, or a special anniversary dinner. To make things a bit easier, I've put together a handy guide covering lots of different date scenarios from daytime outings to evening plans.
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-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 autumn 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, we've got you covered.
Anniversary Date Night Outfit
Of course, it's best to consider the dress code of where you are heading, 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 a date, but it's also a colour associated with romance – and tomato red is one of the key autumn/winter fashion colour trends 2025.
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 tonnes of ways you can wear this colour combination, including wearing a tailored suit with a red blouse or adding red slingbacks to an LBD.
This drop waist dress is perfect for wearing all evening long. The vivid red tone, sleeveless, and maxi silhouette make this dress a glamorous investment piece. On cooler days, add tights and layer up with a tailored blazer
A blazer feels chic, elegant, and sophisticated, making it a go-to for layering over dresses when considering what to wear on a date. Outside of date nights, wear this affordable staple as part of a sleek jeans and a blazer outfit.
If you're scouting for jewellery, Astrid & Miyu is a brand to keep in mind. These earrings are both glamorous and versatile enough to wear every day. They are made from 18k gold-plated sterling silver.
Daytime Date Outfit
For a daytime date, the key is striking a balance between feeling comfortable and looking good, too. If you're planning on being active on your date, such as exploring a gallery or walking around a park, we'd reccomend wearing flat shoes such as ballet flats or Mary-Janes. Denim jeans make a relaxed yet stylish base for an outfit, whilst adding a sophisticated blouse can elevate your whole look.
These high-rise jeans feel vintage-inspired, yet perfectly on-trend. Team with wedge heels for special occasions or chunky trainers for the ultimate comfort.
This neutral blouse features a subtle polka dot print and a ruffle trim, and long 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 office attire, too.
Now discounted in the sale, there is no better time to snap up these stylish Mary-Janes. The cream hue makes these flats extremely versatile, whilst the leather material makes them durable.
Date Night Outfit for Winter
When the temperature drops, your date night outfits might take a little bit of extra thought. We'd recommend looking at the latest coat trends 2025 and investing in a well-chosen coat to become the star of your outfit. However, if you're heading to a venue indoors, like a restaurant, bar, or cafe, what you wear underneath is equally important. Some sleek, tailored trousers that offer full-length coverage and a standout blouse will ensure you look great once you've arrived at your destination, but a warm, cosy coat will do just the trick to and from.
These smart tailored trousers sit high on the waist and offer a wide-leg silhouette and front pleats. Switch out your usual skirts or dresses for some sleek, tailored trousers during the cooler months.
Already firmly on my autumn wishlist, this tie-neck blouse is on-trend, playful, and ideal for building into smarter outfits. It has a tied neck detail that adds to its retro-inspired feel, plus the longer sleeves are great for more coverage when the temperatures drop.
The best winter coats combine style and practicality, and this oversized coat does exactly that. The dark chocolate brown aligns perfectly with the autumn/winter fashion colour trends 2025, and it's made from a soft wool blend that will keep you cozy.
Outdoor's date outfit
Whether you're planning on braving the weather for an outdoor picnic or you're sightseeing around one of your favourite cities, planning what to wear on a date set outdoors should considering several things, from comfort to the weather forecast. To plan for the unexpected, we'd suggest wearing lightweight (and waterproof) layers, some of your most comfortable trainers, and something breathable and comfy underneath.
If you're headed outdoors on a date we'd recommend taking this ultra-chic and shower-resistant trench. Layer this piece over your favourite knitwear, a smart poplin shirt or a floaty dress – it works for a variety of occasions.
This jumper has been made from 100% organic cotton and has an easy-to-wear navy striped style that feels Parisian. Throw this jumper on, combined with denim jeans, tailoring, or even paired with a satin skirt.
With clever cushioned technology, these trainers are a woman&home favourite, with five stars from our testing team. They're a great option for wide feet or anyone with foot issues, so you just know they'll fit like a dream. Read the full review here.
First Date Outfit
First dates are all about projecting your personality whilst wearing something that makes you feel confident and stylish. The setting will naturally guide your choice, but the goal should be to wear something authentic to you. Standout dresses are often a faff-proof option, and don't take up too much time to style. A heeled boot is a stylish yet practical footwear choice, and a top tip is to coordinate your bag and shoe colour or fabric.
This is selling fast according to Boden, and we love the ornate floral print and statement sleeves. If you're on the hunt for the best dresses with pocket this dress features two in the side of the skirt!
Made from real suede leather and coming in a rich tan shade, you'll be wearing these boots for seasons to come. The block heel means that they are comfier than a stiletto; however, they're probably not suitable for strenuous activities.
If you're looking for a new handbag this buckle-design is worth considering. It's made from 100% leather and features a rich tan suede colour that offers versatile styling options.
After-work date night outfit
If you're heading out after work on a date night, you'll need an outfit that transitions seamlessly from office to dinner, and fewer pieces do this better than a satin slip skirt. If you've been wondering how to style a satin slip skirt for evening plans, pairing it with a sleek blazer is a failsafe solution. Swap out your daytime flats for heeled boots to instantly elevate the outfit, giving it a date-ready edge.
This delightful slip skirt will transition seamlessly from AM to PM. Style with chocolate brown boots and layer over a black blazer, both for office attire and for heading out and about.
A cropped blazer jacket is a fail-safe piece of outerwear for when you want to look put together but effortless. Style yours with anything, from special occasion wear to your weekend denim looks.
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, but also comfortable too. A blazer, denim jeans, and a smart blouse make an effortless go-to formula that works for plenty of restaurant settings. 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. To finish, just add a pair of kitten heels if you want extra elegance or style with your favourite flats for a more laid-back feel.
From one of the best French clothing brands, this embroidered 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.
Jeans are an easy 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 casual to smart-casual with ease.
Investing in tailored separates like this chocolate brown blazer is never a bad idea. This doubles as one of the best trouser suits when paired with the matching trousers, and can be worn solo, layered over dresses, casual t-shirts, or light knitwear.
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.
