Planning your date night outfits is one of life’s most difficult fashion decisions. Getting dressed for the office? Formulaic. Throwing on an outfit for a speedy iced oat latte with your bestie? Casual. But when it comes to what to wear on a date – no matter if it’s with a new Hinge linkup or a partner of three years – it can leave you standing in your underwear, staring blankly into your wardrobe.
I’m a bit of a broken record myself and have a go-to rule where I wear ‘normal clothes’ but show a little skin which gives off a low-maintenance vibe. This usually means changing up my work look for midweek dates: I’ve worked in fashion for years, and I often wear outfit combinations that can be too high maintenance for a low-key midweek date. A polo-neck or t-shirt layered underneath an open oversized shirt is my go-to for a Monday, but on a Thursday when I might be heading out for a date after work, I like to spice things up a little. I’d ditch the polo-neck for starters – and I might swap my mom jeans for something with a slimmer fit.
It means planning ahead, which I’d argue is key, because whether you’re dressing up to impress or to feel confident, taking time to consider your features means you’ll feel your best, too.
As a starting point, I’ve made a list of easy outfit formulas for a host of dating scenarios, from chilled coffee meets, to after-hours drinks, chic dinners and beyond…
The date look formula: jeans and a nice top
It’s a classic combination and a dating failsafe. So much so that brands such as Nasty Gal and New Look even have dedicated sections on their website for the look. Denim is definitely date-approved. If like me, you don’t have supermodel-length legs (a girl can dream, right?) opt for black jeans on a date and something with a flattering shape. Rock a flare for that sexy-seventies style or even a skinny-shaped straight leg to stay within the comfort zone. And always high-waisted (yes, I’m ignoring the fact that low rise jeans are threatening to make a comeback). Dress up your favourite pair of jeans with a pretty puff-sleeved top or cami and cardi combo for a lunch date. Add colourful mules for happy hour – you’ll exude effortless chic.
The date look formula: cold-shoulder top and trousers
Well, not literally if you want the date to go well. You can still flash a bit of flesh without looking like you’ve tried too hard. May I present fashion’s solution to the practicalities of staying warm, whilst you expose some skin: meet the slinky knit. Try a style with cut out detail or one-shoulder body. Both work well tucked into high-waisted jeans or tailored trousers. A heeled boot will suit both too and don’t forget stacks of chunky jewellery.
The date look formula: silk and leather texture clashes
Technically leather trousers could be filed under the high-maintenance outfit category, so this one sort of breaks my number one rule. But, in my defence, leather is sexy, so keep it on the radar when planinng your date night outfits.
If you’re unsure the trend will suit you, try a faux version for less, before you commit to full Gwyneth Paltrow in the 90s. You can still embody her minimalism though with a pair of slick leather trousers paired with a silk cami or shirt, for the ultimate texture match. If you’re worried about ending up like Ross Geller at the end of the night, this look also works well with an a-lined leather skirt. Opt for dainty footwear to offset the harsh leather: these strappy mules do the trick.
Read Eliza’s guide to the best leather trousers here.
The date look formula: no fuss dress and stompy boots
Worried about being overdressed for a daytime date? The see this is formula as the ultimate safe bet look which works for a multitude of scenarios – even a cute pumpkin spiced latte pitstop on a dog-walking date.
A smock dress with a little square neck detail is feminine but not too sickly sweet, especially when paired with box fresh trainers. Or go for a mini shirtdress style with knee-high stomper boots for a trip to crazy golf – it’s all about the high-low balance.
Consider your underwear
Lacey underwear makes me feel super confident. So, when I’m planning what to wear under my date night outfits, I’ll always pull a matching set out of the bag (it’s mismatched underwear and socks for the rest of the week though, sorry not sorry). This leads to my final point: when you consider what to wear on a date, the most important thing is wearing what makes you feel comfortable and confident. So, if that means wearing a cute cami which shows off the lace trim of your bra, or a delicate bralette under a sheer blouse gives a little hint of sexy, without giving away too much.