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.
When it comes to dressing for dates, it’s mostly 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.