What to Wear on a First Date: From Casual to Classy (2024)

No matter if it’s your first date in a while, or even your first date ever, we all know one thing’s for certain; that those pre-date nerves are hard to shake off. You want to make the best first impression you can, all while looking and feeling confident. Because we all know that confidence is attractive, and your outfit can give you that confidence boost you may need.

What to Wear on a First Date: From Casual to Classy (1)

Of course, throwing on the first thing you see in your wardrobe isn't going to cut it. You want to navigate the complexities of first date fashion with poise, authenticity and style that showcases you in all your glory. Knowing this is all good and fine, but we still have to conquer the dreaded “what to wear on a first date” dilemma. Before you start panicking and thinking about cancelling, take a deep breath, trust in our advice and read on for our best tips for first date fashion.

First Impressions Last: First Date Outfit

When preparing what to wear on a first date, we have some tips that can set the tone for a memorable evening. Your first date outfit should reflect your personality and make you feel confident. Whether it’s a casual date outfit like a coffee date or something dressier for a dinner date, choosing the right first date fashion is key.

Here are some quick pointers to get you started:

Do Wear What Makes You Feel Good

The secret to a great first date outfit? Confidence! Choose clothes that make you feel comfortable and fabulous. Whether it’s a flattering dress or your favourite jeans, feeling good in what you wear will boost your confidence.

Don’t Try to Be Something You’re Not

Authenticity is attractive. Stick to your personal style—whether casual or more polished. Your first date is about being yourself, not trying to impress with a new persona.

Do Express Your Sense of Style

Let your personality shine through your outfit. Whether it’s bold accessories or unique footwear, embrace what makes you, you. Your date will appreciate your authenticity.

Do Wear Layers

Be prepared for any weather. Layering is practical and stylish. Bring a jacket or sweater that you can easily add or remove based on the temperature.

What to Wear on a First Date: From Casual to Classy (2)

Casual Date Outfit

So you’ve both decided to keep your first date cool and casual. Fantastic! But you still want your first date outfit to make an impression, even if it's laid-back.

For a cute coffee date, the general vibe is laid-back, so whether it's winter or summer, your outfit should reflect a relaxed yet stylish approach. A coffee date outfit winner is always jeans paired with a cosy knit or long-sleeve top if it's cool outside, or an oversized boyfriend shirt in warmer weather. Jean based outfits can include a wide legged denim, a relaxed tencel or even fitted jeans in light or dark denim to give your look some flair. In warmer weather, a sundress is perfect for the occasion, keeping you comfortable and chic.

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These outfit ideas also work for lunch dates, which are generally on the casual side of things.

If your first date is a romantic and fun picnic at the park, you’re likely to be sitting on a picnic rug or folding chairs, so focus on comfortable clothing such as flowing maxis. Or pants like the Breezy Relaxed Tencel Pant in Mid Wash

with its elastic waist, so you can focus on the cute and witty thing you’re going to say next, and not on your waistband that’s digging into your tummy!

Don’t forget you may be doing a bit of walking so choose flats, sneakers or shoes with a small heel so you can enjoy the moment in comfort.

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What To Wear On A Dinner Date

Dinner dates sound formal, but depending on the setting they can range from fromage-formal to salsa fiesta fun! When it comes to choosing a first date outfit for a dinner date, striking the right balance between chic and comfortable is key. Here are some essential tips and date dress ideas to ensure you make a memorable impression.

Embrace your femininity and opt for a dress or a skirt, as trousers can sometimes give off a more masculine vibe unless styled just right. This choice exudes elegance while keeping your look sophisticated yet approachable.

Also, aim for a look that reflects your personal style while considering the evening occasion. A black midi dress is always a classic choice if you're unsure, and can be paired with accessories such as jewellery to add some understated sophistication.

Whether you're naturally bold or more reserved, find a style that aligns with your personality. If you're feeling adventurous, a touch of boldness in your outfit can add just the right amount of intrigue. Right now nothing says bold like the wonderful Lakey Long Sleeve Dress in Jadesheen with its long sleeves and shirred cuffs, offering a modern twist on classic elegance. If you prefer less va-va-voom for what to wear on a dinner date, the Hazel Short A-Line Tunic Dress in Soho is refined, understated yet elegant at the same time.

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Lastly, prioritise comfort. When you feel at ease in your outfit, it shows. Confidence is key on a first date, so choose something that allows you to shine while enjoying your evening.

Staying True To Yourself: Personal Style and Confidence

Remember, the best first date outfit is one that makes you feel confident, comfortable, and authentically you. As mentioned before, your first date isn’t the time to get radical with your outfit and try to fit into a mould of what you think your date would like. Instead, stay true to yourself and your personal style. How to dress on the first date is all about what makes you feel comfortable, confident and true to yourself.

Strike that balance, and you're sure to impress while enjoying a wonderful dinner date.

Fingers and toes crossed! Adrift xx

Discover what to wear on a first date with Adrift’s impressive collection. Whether it's a laid-back coffee outing or a sophisticated dinner date, find outfits that exude confidence and allure. Shop now and set the perfect tone for your romantic rendezvous!

What to Wear on a First Date: From Casual to Classy (2024)

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