6 Easy Outfits That Will Make You Feel Your Best on a First Date

Knowing what to wear on a first date is no mean feat. With the added nerves and apprehension, it’s a recipe for frantic last-minute wardrobe scrabbles. Pre-first-date nerves are a rite of passage, but another concern is knowing where to start with your fashion choices. What I've learnt most from working in the fashion industry is the importance of comfort, and contrary to popular belief, that philosophy extends to date dressing. As the result of far too many saccharine rom-coms (conveying the lengths people go to appease a lover), the context of date dressing has become scrambled.

Although we’re familiar with wearing towering heels and tentatively skipping pavement cracks, the reality is that in those situations, you’re less likely to put your best foot forward. I used to think date dressing was akin to one of two options: either figure-skimming cuts or flirty tea dresses. There’s value in both, but in reality date dressing is whatever you make of it. The choices are endless and ultimately, yours to make!


(Image credit: @chloepierreldn)

However, when it comes to dressing for a first date, there’s a general rule of thumb I think always works. First is the art of subtle elevation. Much like the no-makeup makeup look, there are little details that’ll quietly elevate a look, like jewellery, a sleek bag or tailoring with strappy heels. The second is comfort. If you’re not a heel wearer, opt for something you feel relaxed in. Slip-on mules are equally chic and in general, feeling comfortable always boots one's confidence, right?

Dressing for all eventualities is a form of empowerment. Of course, the type of date has a bearing on your outfit choice, as you’re less likely to turn up to a picnic in 10-inch stilettos. (Although, if that’s what you fancy, wear them with pride!) between miniskirts and mary-jane shoes, there’s an evident playfulness with this season’s most famed pieces—so there are various options if you’re looking for something alluring. However, I believe that the bones of a wardrobe are the best fashion allies when we want to look and feel our best—the oversized shirt, a midi elevated with sleek accessories or a great skirt.


(Image credit: @natashandlovu)

But above all, it’s about feeling like yourself. If you could do with inspiration for date outfits or want to refresh your wardrobe, we have six outfits that will take you from day to date night in no time at all.

1. Off-the Shoulder Top + Midi Skirt + Mules


(Image credit: @sylviemus_)

Style Notes: Although this is a refined look, it's also a formula to refer to if you're planning a more laid-back evening date. A column skirt, Bardot top and heels always look polished. Barely-there jewellery will amp up this ensemble even further.

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2. Maxi Dress + Silk Overshirt + Mary-Janes


(Image credit: @vikilefevre)

Style Notes: A maxi dress is perfect for all occasions, and a longer hemline will make you feel carefree. Switch your sky-high stilettos for flat or low-heel Mary Janes to balance things out.

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3. Light Knit + Leather Trousers+ Flats

first date outfits

(Image credit: @lucywilliams02)

Style Notes: It might be spring, but light knits still reign supreme, so this layered look works well for outdoorsy dates too. Leather trousers and a bag an equally glossy finish will leave the look feeling sleek and polished.

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4. Black Co-Ord + Strappy Shoes


(Image credit: @marina_torres)

Style Notes: You can always count on a two-piece to look good from day to night. This outfit is one to go with if you want to look uniform in very little time. Add simple accessories and you're set.

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5. Oversized Blazer + Lingerie Slip Dress + Sling-backs


(Image credit: @tylynnnguyen)

Style Notes: A showstopping dress you feel good in will instantly boost your confidence, especially when paired with striking matching accessories. A slip dress and blazer are two of the hardest-working fashion items. For the evening, wear the blazer over your shoulders and show off every inch of the dress. Black heels and a shoulder bag will go with whatever colour dress you choose.

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6. Cropped Jacket + Jeans + Heeled Boots


(Image credit: @emmanuellek_)

Style Notes: You can't go wrong with jeans, heeled boots and a nice top, or in this case, jacket. Details like gold buttons and a sleek handbag add extra polish.

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This story was originally published at an earlier date and has since been updated.

Freelance Fashion Editor

Avalon Afriyie is a freelance writer and storyteller based in London. She specialises in sustainable fashion, health and the narratives of marginalised communities. She has a background in fashion show production and styling, having previously worked on The Clothes Show and with the Lyst Group. Since graduating in 2013 with a BA (Hons) in English and contemporary media, she’s worked as a feature writer for an independent publication and a contributor for Quill’s creator network. She now marries her passion for words and style, writing for some of the most esteemed fashion and lifestyle publications, Who What Wear UK and Stylist. Avalon also provides copywriting services, creative consultancy, and visual media for independent businesses, including travel guides, interviews, press releases and blog posts. Her work has been featured on Lush, Contiki, Youswim and Ohne. She spends her days writing to her heart’s content for business and pleasure, shooting on film and dreaming of residing a stone’s throw away from the ocean with her love and a pup (clad in a sweeping frock, of course). She’s currently penning ideas for a book of personal essays and free verse poetry on love, life and the stages in between.