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 date dressing is whatever you make of it.
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 plush bag or tailoring with strappy heels. Second is comfort. If you’re not a heel wearer, opt for something you feel relaxed in. Slip-on flats are equally chic.
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!) There’s an evident playfulness with this season’s most famed pieces—cut-outs, minis and ankle-strap heels—so there are various options if you’re looking for something alluring. 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 and jeans, a daytime midi elevated with sleek accessories or tailored trousers paired with a décolletage-bearing top.
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 nine outfits that will take you from day to night.
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.
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.
Autumn/winter is the time for moody prints, from abstract motifs to dark florals. Add a pair of knee-high boots to keep your look feeling sleek and polished.
My top tip for this look? Half-tuck the shirt or undo the last few buttons and tie it to show off the fringing. Round the outfit off with some fun accessories that match the skirt’s energy.
Tailoring is undefeated. I’d wear a smart pair of trousers with a cut out top and have my hair in a low bun to show off the finer details and jewellery.
A dress is perfect for all occasions, and a shorter hemline will make you feel flirty and carefree. Switch your sky-high stilettos for low-heel Mary Janes to balance things out or opt for boots.
This is a formula to refer to if you’re planning a more laid-back date. A well-fitting pair of jeans and heels always looks polished, and jewellery will amp up this ensemble even further.
There something ultra-classy about white jeans. Paired with a detailed top, it’s a good way to celebrate a staple. Ballet flats are casual shoes, so they always complement pared-back looks for date days. Or, swap in a heeled mules.
A showstopping dress you feel good in will instantly boost your confidence, especially when paired with striking matching accessories.
This story was published at an earlier date and has since been updated.
