There’s one big question that every woman struggles with at some point in their life: What is the best thing to wear on a first date? Should you go classic and stick with a little black dress? Perhaps it’s more of a bold-frock, “here’s who I really am” type of situation. Maybe, just maybe, you don’t want to wear a dress at all and would be much more comfortable wearing a pair of jeans. However you feel about the other elements surrounding a first date (the person actually being the person they’ve said they are on the app being a primary concern), it’s inevitable that you will stress out about what to wear.
But worry not—we’ve rounded up a few outfit ideas that will work for every kind of date. There’s just one rule we stick to: make sure you feel good and really comfortable in what you wear. Whether that equals a comfy dress that you can wear your battered Converse with or a skirt that shows off a little leg, there’s plenty to choose from for that all-important first date. Scroll on to see eight outfits that nail what to wear on a first date. Plus, you can shop the looks right now.
Style Notes: Not everyone wants to go for the short-skirt option, but there are ways of feeling date-ready without showing off your pins. Try a pretty top and your favourite pair of jeans. This outfit is a guaranteed confidence booster.
Gold Lurex is the perfect option for a low-key but fancy top.
Favourite jeans amongst style influencers.
I know these shoes are going to fly.
Style Notes: For an evening spent sipping wine and getting to know each other, tailoring makes for an ideal solution. Wide-leg trousers such as this are perhaps the comfiest thing you can wear—second only to leggings, perhaps—while the crop-top-and-blazer combination up top will showcase what an adept dresser you are.
Double-breasted blazers always look so expensive.
I love the thick, bra-covering straps on this crop top.
H&M has perfected its wide-leg-trouser offering this season.
Style Notes: The midi dress is a classic for a reason. It is universally wearable and can be dressed up or down depending on your date activity. If you’re unsure of the dress code, a pair of heeled knee boots strike the perfect in-between balance and will give any dress a fashionable edge.
This Reformation dress creates the sleekest hourglass silhouette.
There’s no outfit these earrings can’t elevate.
These boots also come in an ankle length should you prefer.
Style Notes: Jeans and blazers go together seamlessly. (And hopefully, you and your date will too!) If you’re stressed about matching up your separates, stick to classic colours, then add accessories that reflect your personality.
This blazer comes with an extended size range.
These jeans come in a plethora of blue shades as well as two tones of grey and black.
Green accessories are still trending.
Style Notes: The minidress made a big comeback this year. You need only see the multitude of thigh-length hemlines on the runway for clarification. A black minidress is a timeless option which works for an array of dates. Again, if you’re not sure how elevated you should go, try laying a shirt over the top of your minidress. It’ll make it feel more casual if you end up going for a low-key dinner, but you can also sling it off should you find yourself somewhere fancier.
The fabric on this shirt drapes so beautifully.
A simple LBD is one of the most versatile style investments you can make.
These look so premium—no one will guess they cost £45.
Style Notes: There’s something to be said for simple first-date outfit combinations. This triad of a chunky chain necklace, silk camisole, and black trousers is a no-fail solution.
I own two Laura Lombardi necklaces, and they’ve never hinted at tarnishing.
An easy top option you can pair with jeans or slip skirts.
When it comes to black tailored trousers, Arket has nailed the staple.
Style Notes: Not a dress or jeans type of person? Try a miniskirt paired with an on-trend leather blazer for a look that’ll impress your date in the style stakes. Minimal silhouettes and easy jersey staples, such as a T-shirt, will keep the look effortless.
This oxblood colourway makes a change from classic black leather cover-ups.
This & Other Stories tee comes in so many colours.
The bouclé texture feels so on-trend.
Style Notes: Just want comfort? Fear not; a Breton tee and loose jeans can totally work for a first date, be it to grab a coffee on a walk or to do something more active like bowling.
A top every wardrobe would benefit from.
The Y2K aesthetic is still going strong—cue my ongoing obsession with shoulder bags.
