8 Elevated Outfits That Are Ideal for a First Date
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.
1. Nice Top + Jeans
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.
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Gold Lurex is the perfect option for a low-key but fancy top.
2. Tailoring + Crop Top
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.
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3. Midi Dress + Knee Boots
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.
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4. Checked Blazer + Skinny Jeans
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.
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These jeans come in a plethora of blue shades as well as two tones of grey and black.
Green accessories are still trending.
5. Minidress + Oversized Shirt
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.
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A simple LBD is one of the most versatile style investments you can make.
6. Silk Camisole + Black Trousers
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.
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I own two Laura Lombardi necklaces, and they've never hinted at tarnishing.
When it comes to black tailored trousers, Arket has nailed the staple.
7. Blazer + Miniskirt
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.
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This oxblood colourway makes a change from classic black leather cover-ups.
8. Breton Top + Loose Denim
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.
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The Y2K aesthetic is still going strong—cue my ongoing obsession with shoulder bags.
Next Up: The 9 Most Expensive-Looking Pieces on the High Street This Week
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.
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