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!
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.
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
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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The exact Reformation piece Sylvie is wearing is no longer available but this Bershka version is a perfect dupe.
Midi skirts come around like clockwork every season but ecru denim elevates this style even further.
These slip-on mules will never date. Although it's cold outside you can wear them for evening dates indoors.
The slight dip elevates this classic bag into a cool hammock style.
The Victoria X Edge of Ember collaboration has given us some real diamond pieces. The Marquise is a simple necklace you can pair with anything for a slight hint of sheen.
2. Maxi Dress + Silk Overshirt + Mary-Janes
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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Maxi dresses can so easily be dressed up or down depending on the location of the date.
With Nothing Underneath's silk collection boasts some sleek pieces for fancier occasions. Wear it unbuttoned over dresses or tucked into trousers.
Judging by the popularity of mary-janes, I predict this will be a bestseller for Aeyde.
I can't stop thinking about this romantic embellished bag.
Call me a hopeless romantic if you will but you have to wear some form of heart on a date. Non?
3. Light Knit + Leather Trousers+ Flats
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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Top-tier knitwear.
The very definition of dressing for confidence.
A new spin on a classic shoe you can wear for date night and beyond.
This bag is about to be so popular.
4. Black Co-Ord + Strappy Shoes
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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You can effortlessly interchange this co-ord for other events.
A sleek skirt with added slit detail.
Misshapen earrings are perfect in my eyes.
This looks very premium.
The quality IRL looks so great.
5. Oversized Blazer + Lingerie Slip Dress + Sling-backs
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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Every fashion editor owns this blazer. It's a classic for dates, work and weekends.
My love for this dress knows no bounds. It's the ultimate date-night (or occasion) dress with romantic lace applique and a fluted hem that encourages sway.
Sophistication in a shoulder bag.
A classic slingback you can wear with dresses and jeans alike.
Molten organic-shaped earrings with a dangly pearl. This regal style will offset the androgynous blazer and finish the outfit.
6. Cropped Jacket + Jeans + Heeled Boots
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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Pair with jeans and leather trousers or even a slip skirt or dress.
How perfect is the wash on these jeans?
Fashion girls love low-heeled ankle boots, and for good reason. These are a beautiful quality and the perfect heel height to ensure they will be a wardrobe hero for years to come.
Next Up, I've Done the Research—These Are the 8 Best Shoes to Wear With Midi Dresses in Summer
This story was originally published at an earlier date and has since been updated.
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