When you’ve been in a relationship for as long as I have (we’re talking 16 years), it’s not unusual for date nights to lose their sparkle. Though, when I speak to my single friends about their upcoming dates, often, they too are less than enthused about prepping for them. Gone are the days, however, when “sexy” was the dress code to adhere to for date nights. Whether it’s your first or 50th, it’s important that you stay true to yourself and wear an outfit that reflects who you are and your individual style.
Still, no matter how self-assured you are, there’s always the conundrum about how fancy your outfit should be. Are jeans too casual? Will heels make me look overdressed? To help cover all of your date-night outfit needs, I’ve scoured the internet to find 12 impressive looks that’ll work for low-key daytime meetings all the way to late-night dinners in the most exclusive restaurants. What’s more? I’ve also found the pieces to re-create them. Scroll on for your ultimate date-night outfit guide.
Style Notes: Leather blazers have the power to give any outfit a cool overhaul, including pretty dresses.
A blazer I always come back to.
A dress fit for so may occasions.
Who doesn’t love statement arm candy?
Style Notes: Jeans and a nice top will always serve you well. For fashionable kudos, opt for straight-leg denim and a satin blouse.
The halterneck adds an evening touch.
High-rise jeans look great with tops tucked in.
A block heels adds comfortable to these shoes.
Style Notes: If you know your date is going to take a fancy turn, slip into velvet suiting for the perfect formal but fashionable balance.
A single-breasted blazer always looks effortless.
Wear with the matching trousers, or switch in a faux-leather pair.
Sparkly shoes will elevate any look.
Style Notes: Dresses are always a date-night fail-safe, but skirts and tops look just as sleek. Stick to monochromatic or neutral palettes, and you can’t go wrong.
A top you can wear with jeans and trainers, too.
I own a miniskirt just like this and get so much wear out of it.
If in doubt, I always add a chain necklace to my outfits.
Style Notes: Wide-leg trousers are now a wardrobe staple, whether you wear them to work or at the weekend. Make them feel more “date night” with a sweetheart-neckline top and a top-handle bag.
This silhouette continues to be so popular.
Black and brown is such a luxe combination.
A bag you’ll carry for the rest of your life.
Style Notes: The appeal of suits and co-ords is that they take all the effort out of assembling your outfit but look seriously pulled-together.
I just know this set is going to fly.
A barbiecore moment.
Now this is a beauty.
Style Notes: Is there any occasion a little black dress doesn’t work for? This year, the best options feature subtle rhinestone embellishments, which can be dressed up or down depending on your date location. If it’s on the fancy side, up the ante with a beaded bag.
My dream dress.
This looks just like the designer iterations that came before it.
Finish with a simple hoop.
Style Notes: If you’re still not sure whether to dress smartly or casually for your date night, turn your attention to the cardigan. With the ability to make even the fanciest dresses feel more casual, pair yours with a frock in a similar colour, and finish with whatever shoes you feel most comfortable in.
Fluffy knitwear always feels so luxurious.
A versatile dress staple.
You’ll always get the wear out of a pair of classic tan knee boots.
Style Notes: The last thing you want to be is cold when the sun goes down, so why not make your jacket the focal point of your look? Look for streamlined styles that won’t look odd being left on, and wear them with a simple top, jeans and mules.
I’ve had my eye on this jacket for months.
These went straight into my basket.
Follow Carrie Bradshaw’s lead, and make every date night a Manolo moment.
Style Notes: Minidresses and knee boots are one of my favourite outfit combinations and always my go-to for cocktail-based date nights.
I always look for minidresses with long sleeves.
Complete the look with statement earrings.
White boots will make every outfit you wear them with feel fresh.
Style Notes: We’ve already covered the fact that co-ords are a date-night style saviour. If you love clashing colours, try wearing a bright two-piece with a pair of statement boots or a bold bag.
This tank-and-skirt set is so cute.
Charles & Keith’s shoulder bags could easily pass for designer.
Mock-croc finishes always look so expensive.
Style Notes: Monochrome dressers, this one is for you. Washed black jeans feel more evening-friendly than classic blue, especially if you add heeled pumps.
Easy to dress up or down, depending on the date.
Arket has so many flattering cuts to choose from.
It’s date night, so why not treat yourself?
Next Up: Wimbledon Is Here—These Celebrity Outfits Are Serves in Their Own Right
This story was originally published at an earlier time and has since been updated.
