If you find dressing for low-key dates a total minefield, you're not alone. When it comes to casual date outfits, how casual is too casual? Should you wear small heels, or go for complete comfort and opt for flats? Is a short dress too dressy for the daytime? These are questions we can all relate to when choosing the perfect date outfit. It's no wonder most of us resort to an easy top-and-jeans combo and wind up feeling underdressed.
To avoid that gut-wrenching regretful feeling, we've turned to a few of our favourite influencers to show us how to be prepared for every kind of casual date eventuality. Sure, they may not be on an actual date themselves, but their mix of style and practicality—think chunky kicks with slinky slip skirts or and a boxy denim jacket worn over a midi dress—is giving us all kinds of good ideas. Scroll below to see and shop five casual date-night outfits to copy on your next one.
Style Notes: Showcase your fashion flare by opting for a pair of standout trousers—be they bright or printed—then give them a relaxed overhaul with a leather biker and plain boots. Ideal for Saturday strolls, grabbing coffee or hitting the bar on a week night.
Invest in a good-quality leather jacket and we promise you'll wear it for years to come.
Achingly cool, try tucking this tee into ladylike skirts, too.
The high-waist cut of these trousers will flatter all body types.
Get in on the beaded bag trend with this pearly style.
Burgundy leather boots make for a fresh alternative to classic black.
Style Notes: You're off out for dinner but you have no idea which restaurant has been booked. For all you know, it could be a pie and mash down the local, or a seven-course taster menu at a fancy joint. In this situation, we recommend a fluid shirt dress, as the wide shape will give it a relaxed vibe. Keep your accessories to a minimum, too—simple strappy heels will never go amiss.
This versatile frock comes in three other prints. At that price, we'll take one of each.
Try looping the long chain twice around your neck for an easy layered look.
You'll get so much wear out of these simple sandals.
Style Notes: Universally flattering and easy to style, wrap dresses are ideal attire for casual dates as they can be worn in a multitude of ways. Our favourite, however, has to be with an oversized cardigan slung off one shoulder, simple hoop earrings, and your choice of trainers, low-heel boots or loafers.
Buy this cardigan a size-up to really hone the slouchy vibe.
Try wearing this pretty printed dress with a roll neck and white boots.
The perfect hoops for under a tenner? Sold.
Style Notes: There's no denying that slip skirts can look slinky if that's your intent, but we think they work just as well for chill dates, too. Pair it with a fine roll neck top, a chic coat and box-fresh kicks for a cool high-low take on the trend.
The thin weave of this roll neck is ideal for layering underneath a slip skirt as it won't look bulky.
We're amazed this skirt is still in stock, so act fast.
Staud's Bisset bag is still going strong on the Instagram scene.
The closest you'll get to walking on air.
Style Notes: To grab brunch or for cinema pre-drinks, turn down the heat of thigh-split frocks with a pair of ladylike block heels and an oversized denim jacket.
Topshop's sell-out dress is back.
We love this edgy perspex take on the classic toe-cap shoe.
Heading to a fancy restaurant with your significant other? Then you'll need another outfit entirely. Don't worry—we've already found it for you...