Whether it’s a trip to the theater, dinner with drinks and a movie, or a casual meet up for coffee, we have the outfits to inspire your upcoming date night look right here! From first meetings with a new crush to yours and spouses’ tenth anniversary, there’s nothing like feeling totally confident and beautiful as you step out for a romantic encounter. So, take your pick from swishy feminine gowns and heels to comfy and cool ensembles with sneakers. Whatever speaks to you, your style and location of your special date! 

Want to see the looks?!

Go ahead and keep on scrolling…


We love how many incredible dress styles there are almost as much as we love the ease of wearing them! No need to try and coordinate the colors of each individual piece in your look, simply slip into your favorite frock and you’re all set. All that’s left to do is find the perfect heels and accessories…

A Printed Dress

Woman in printed dress on street

Jan Zahradka / Shutterstock.com

Do you love prints as much as we do?

Then this is the outfit for you!

There’s no shortage of printed dress out there meaning it’ll be a simple task to find one that suits you and your style! Opt for florals and leaf prints in fresh shades such as white and soft yellow as we near the spring and summer seasons. Alternatively, whilst it’s still pretty chilly out there, floral prints on a darker base such as black or navy are perfect over tights to keep you warm in style! Why not wear yours with heels in a coordinating color to your chosen print? This will lengthen your silhouette and enhance that gorgeous pattern. 

A Romantic Pink Dress

There’s no doubt about it, date night should be all about romance! Make sure you embrace that love in the air and opt for a beautiful, blush pink dress next time you plan to meet your love! We adore the soft, feminine hue of pink dresses like this one and how they look just a pretty with heels as they do with flats. Opt for a maxi like the Club L London high neck long sleeve maxi dress by Asos to give your look an additional air of romance. Alternatively, keep things playful with a mini length pink dress. Whatever style you decide on, you can’t go wrong with a sweet shade of pink on date night!

A Leather Dress & Boots

If the 2020 runways are anything to go by, you can expect to see soft leather pieces everywhere this year. Pieces in buttery shades, as well as those in deeper hues, will make up a fair few of our staple items and we’re seriously excited about the edgy vibes it’ll give to our closets! Try this gorgeous trend for date night and opt for a sultry leather dress and coordinating leather boots. You’ll feel fierce and confident, not to mention incredibly beautiful! We adore this deep burgundy shade at this time of year and will no doubt be pairing ours with a killer pair of sunglasses and a statement clutch next date night! Get the look with the Burgundy leather-look belted dress by Shein.

A Maxi Dress & Heels

You just can’t beat the classic combination that is a maxi dress and heels. Not only does it lengthen your silhouette but it also gives you a look of effortless sophistication that’s simply ideal for date night. This look is also incredibly versatile meaning it’ll work just as perfectly for impromptu evening drinks as it will for dinner and dancing. Choose a shirt style maxi dress with a loose fit and waist-cinching, self-tie belt then style it with strappy heeled sandals for extra style points. Your date won’t know what hit them!

A Classic Red Dress

Woman in red dress on street

eversummerphoto / Shutterstock.com

Looking for that perfect Valentines’ outfit?

You’ve come to the right place!

In the way of romance, there’s nothing more fitting than the perfect red mini dress. Opt for opulence with a ruffled skirt and sleeves or even an alluring lace insert. Nothing is too dramatic when it comes to red dresses for a date and we highly recommend coordinating your shoes to match as pictured! Finally, a sleek up or down do is best when it comes to styling. This will keep your look elegant and polished so you feel amazing at dinner, drinks, or even a trip to the theater. 

A Maxi Dress & Flat Sandals

It may still be sweater weather but we can’t help dreaming of those not-so-distant spring days! With that in mind, we’re planning out all of all the ways we can style beautiful maxi dresses with flat leather sandals to head out on a, slightly warmer, springtime date! Opt for florals, cotton constructions, and floaty skirts to make the most of this incredibly pretty outfit. A maxi shirt dress is also a great way to balance out the casual component offered by your flat sandals. Just like the beautiful Whistles stripe wrap shirt dress from Asos. A dress like this one is perfect for a semi-casual coffee or on a lunch date.

A Midi Dress & Sneakers

Talk about keeping it cool! This outfit is one of our favorites as it not only looks great but feels amazing too. By choosing a beautiful fitted midi dress you will definitely look as though you’ve made an effort. Meanwhile, styling your dress with your favorite pair of sneakers will give your overall look an edgier vibe whilst making sure you feel comfortable all date long! Try a fitted midi with some stretch to exude those smart/casual sporty vibes on your date!

A Beautiful White Dress

There’s no need to save white for your wedding!

Let us show you why…

When the occasion calls for a look that’s undeniably pretty, you can’t beat the ethereal nature of a crisp white dress. Whether you opt for a mini, midi or maxi length, you’re certain to feel incredible, especially when you cleverly contrast that fresh white shade with a bold red lip! This style of dress is ideal for a romantic lunch at an outdoor venue, an early evening dinner date, or even, meeting the parents! Opt for puffed sleeves and a high neckline for a look that’s supremely elegant and also right on-trend. This style is perfectly captured by the beautiful smocked chiffon dress by H&M. 

A Boho Style Dress

We adore boho dresses, not only for their carefree, vintage-inspired vibes but also how freeing they feel on our bodies! Just because you’re heading out on a date, doesn’t mean you need to wear anything skin tight, uncomfortable or something that doesn’t feel like you. Therefore, boho style dresses are perfect for a look that’s outwardly pretty and charming but still allows comfortable movement. If you can find something in a stunning shade of mustard yellow like this dress, well, that’s even better!

Skirts And Tops

These varying looks are absolutely perfect for date night. Go for something casual and pair your skirt with a slogan tee and sneakers for a coffee date, or amp up the formality with a shirt and heels for dinner! 

Not convinced yet?

You will be!

Read on and discover the many different ways you can style your skirts to suit any and every date location imaginable!

A Shirt And Midi Skirt

Woman in printed skirt on street

DKSStyle / Shutterstock.com

We adore this outfit for evening drinks, dinner, or both! You’ll wow your date with your elegant and polished style with next to no effort. All it takes is your favorite fitted shirt tucked neatly into the midi skirt of your choice. Throw on a pair of heels and you’re ready to step out! This will work beautifully with a flared skirt like the one pictured or something more fitted if that’s what you prefer. The main requirement is that it’s a midi length, this will keep your look timeless and classic. We also recommend a plain shirt and a skirt with a print of sorts, or visa versa. 

Can’t find what you’re looking for?

No problem. We have you covered!

Slip into the floral printed midi skirt by Zara and tuck in your fave plain shirt to instantly achieve this look. For added style, add a pair of heeled sandals and roll up the sleeves of your shirt with the top few buttons left open. For more tips and hints on wearing prints, check out these 11 Celebrity-Inspired Ways To Wear Polka Dots!

A Floaty Skirt & Matching Sweater

Comfort and class combine with this next date night outfit! Choose a floaty midi of maxi skirt then throw on a matching sweater and you’re practically done! We recommend choosing items in the same hue for an extra chic finish though this outfit totally works in pieces that aren’t the same color too. Leave the sweater loose for a slouchy, cool-girl vibe or french tuck your sweater for a slightly smarter, waist-defining ensemble. Finally, throw on the shoes of your choice! This outfit works as brilliantly with boots as it does with sneakers or heels. 

A Neutral Monochrome Outfit

Woman in monochrome outfit on street

Luca Ponti / Shutterstock.com

Look no further for the trendiest date night look out there…

We have it right here!

If you’ve scrolled through Instagram, opened a fashion magazine or, you know, been outside in the last month, you’ll probably have realized that monochrome outfits are very very in! We love how they work with a skirt and top combo and can’t wait to rock it on our next romantic occasion! To embrace this trend for your next date night, we recommend opting for a neutral pallet in soft pastels or earthy tones to keep it chic. Just like Skyla knitted midi skirt and coordinating Suri crew neck sweater both by Reiss. The choice is yours of course and the beauty is this trend will work in whichever color you desire. Finish off your on-trend date night outfit with boots, a red lip and, weather permitting, a gorgeous pair of sunglasses!

Pants And Tops

Whether it’s just not the weather for dresses and skirts or you simply prefer to wear pants, we have the most gorgeous outfit ideas for your next date night! Keep things on the casual side in your favorite pair of jeans or style up your look with tailored pants for evening plans. You’ll have all eyes on you wearing any one of these irresistible outfits…

A Statement Sweater

Woman in jeans and printed top

eversummerphoto / Shutterstock.com

There’s nothing like a statement sweater to instantly breathe new life into your favorite fitted jeans! If your date is on the casual side such as bowling or breakfast, go ahead and throw on a pair of boots or sneakers. Your sweater will still steal the show! When an evening date such as dinner or drinks and a movie is on the cards, however, you’ll want to arrive semi-casual but with a dressier element going on. This is the time to add heels! No matter how you style this outfit, just ensure your sweater is the center of attention like the Black & white mixed animal jumper by Topshop. Finally, give it a French tuck to define your silhouette!

A Sweater & Slouchy/Smart Pants

Pull out your basic sweaters and get ready to fall in love with them all over again. Simply by tucking them into a gorgeous pair of slouchy pants, you’ll discover the smart/casual date night look of your dreams! We’re pretty much obsessed with the slouchy belted pants by Bershka, available in cream, black, turquoise, and grey. We promise we won’t tell if you go ahead and purchase all four! Finish off with a pair of heels or heeled boots (this will also look incredible with sneakers) and a smart long coat. You’ll be the chicest date they’ve ever laid eyes on! 

Jeans & A Coordinating Coat

As we mentioned before, the monochrome look is most certainly on trend right now! The beauty of this trend is not only how chic is comes across but also the fact you probably own enough items to make a fair few looks already! So, for your next date night, try matching your top half to the color of your favorite jeans, black if they’re black, blue if they’re blue, you get the idea! We’re loving this tonal outfit and how easily it can be thrown together whilst looking so elegant and planned out. Once you’re done matching up these pieces, throw on a killer pair of heels and a slick of red lipstick for a romantic edge! You can even make sure your hair looks the part with our 18 Expert Tips For The Secret To Shiney Hair!

Whichever look you decide to rock on your upcoming date, make sure it feels comfortable and, most importantly, like you. Undoubtedly, you’re going to look stunning in any one of these perfect date night outfits!