5 Casual Date Outfits of the "I Just Threw This on" Variety

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.

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Edge Up Statement Trousers
(Image credit: @lucywilliams02)

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. 

Related: Camel Coats Always Look Elevated—28 That Get This Fashion Editor's Approval

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Look For Relaxed Fits
(Image credit: @monikh)

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. 

Related: Summer 2019 Fashion Trends: Looks You Need to Know

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Spin Your Favourite Wrap Dress
(Image credit: @asos_lesley)

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. 

Related: What to Wear on a Date: 7 Confident, Stylish Outfit Ideas

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Dress Down a Slip
(Image credit: @_jessicaskye)

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. 

Related: No Biggie—I've Just Found Your Best-Fitting Jeans to Date

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Throw On A Denim Jacket
(Image credit: @aglaelovinyou)

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.

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... 

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o.

Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.