Looking for date night outfits? Here are 7 fail-safe looks that work for everything from anniversaries to casual daytime dates

Deciding what to wear on a date can feel overwhelming, but the right outfit changes everything. From wedding anniversaries 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 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 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 dinner reservations. We've got you covered.

Anniversary Date Night Outfit

It might seem cliché to wear red on date, 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.

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.

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.

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.

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.

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.

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.

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.