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What to Wear On A Casual First Date


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First dates are certainly nerve-wracking, that’s why casual first dates are perfect for beating those awkward silences. Casual first dates remove the pressure of ‘dating’ so you can sit back, relax, and get to know the person in front of you.

With so many options for a casual first date, we have removed the stress and worry for you and compiled a list of casual first date ideas and what to wear to them. Whether you’re heading out for a walk in the park or exploring your local museum, we have the ultimate guide on what to wear on a casual first date.

Casual First Date Ideas

  • Play Mini Golf: With so many mini golf centres popping up across the country, what better time to jump on the craze than on a first date? It’s a great way to have fun and see each others competitive side.
  • See a Band – If you’re feeling really nervous about talking, why not book tickets to see a local band? And if you’re feeling it after, you can always go and get some drinks.
  • Grab a Coffee – What better place to go on a first date than your favourite coffee shop. Guaranteed comfort when you know the place inside and out!
  • Watch a Film– We know it’s a cliché date idea, but heading to the cinema is the perfect way to enjoy someone’s company with no pressure attached.
  • Head to a Sporting Match – If you enjoy football or ice hockey and want to support your local team, what better way to get to know someone than at a sporting match, and you don’t have to worry about dressing up.

Walk At The Park First Date Outfit

Fancy going for a stroll around your local park? This is the perfect option if you love the outdoors and you can take your time getting to know someone, whilst enjoying your surroundings – and it’s free!

Opt for outfits with breathable and stretchy material that isn’t restricting your figure. You want to keep comfortable throughout, so choose something you can dress up as much as you want. We’ve picked out two of our casual dresses ideal for a first date.

Made from a comfortable jersey fabric, this midaxi dress is floaty and lightweight and features two side pockets. Available in stunning cobalt blue, burgundy, khaki green, and timeless black, complement this dress with a denim jacket and canvas trainers to keep those blisters at bay.

Fresh in floral print, this stunning midi dress is perfect for a first date at the park. Similarly to the previous dress, this floaty number is lightweight and will keep you cool on your walk. Available in various designs, this dress features a stunning v-neckline, frill hemline, and short frill sleeves. Wear with sandals and a jacket for an effortless everyday look.

Shop tall casual dresses.

Concert First Date Outfit

If you’re looking to see a band for your first date, this is the perfect idea to keep the conversation flowing as much as you want whilst you enjoy the music.

At a concert, feel free to add a little edge to your outfit. We have picked out two of our favourite casual concert date outfits.

Ticking off that edgy look, we have our trend-led cropped jeans, made from cool cotton fabric they feature a wide leg style, high waist, and belt loops. Complement with a day top, or better yet, the band’s t-shirt if you’re a big fan and trainers for an easy on-the-go look.

Looking for something to make more of a statement? Turn to our bright pink twill trousers in a cropped finish. Made from 100% cotton, these twill cropped trousers will keep you cool and comfortable throughout the concert. Complement with sandals and a parka jacket if you’re outside, just in case the weather decides to take a turn.

Shop tall cropped jeans.

Drinks At A Bar First Date Outfit

If you’re in need of some Dutch courage, a first date at a bar is the answer. You can always leave a little early if you’re feeling awkward, but if the drinks are flowing and it feels right, it’s the perfect place to relax and get to know someone. You can always find a bar that has games inside as an icebreaker.

This is your chance to dress up your outfit with statement trousers or bright tops, you can always keep it casual with your footwear choice and accessories.

These stunning trend-led swirl trousers are the perfect statement piece to lighten up any room. The ideal outfit to make a lasting impression, these marble print satin trousers are lightweight, and feature a high elasticated waist, side pockets, and are finished in wide-leg style. Elevate your look further with strappy heels and a blazer jacket to polish off your look.

Another stunning pair of wide leg trousers in gorgeous swirl print that matches the casual vibe. Available in bright orange and bright green, these trousers feature a high elasticated waistband to cinch you in at the waist as they effortlessly elongate your legs. Dress down your outfit using an oversized crisp white shirt, vest top, and mules for a trend-led look you can wear on repeat.

Shop tall wide leg trousers.

Cinema First Date Outfit

The cliché date that everyone loves! Heading to the cinema is the perfect choice when you’re worrying about the conversation drying up and is great for an icebreaker first date. You don’t have to worry too much about your outfit for this first date as you’re sitting in the dark, but even so it’s always nice to make a good first impression.

We have picked out two of our best jeans and a nice top outfits, ideal for a cinema date.

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A more casual dress code is needed for a cinema date however, you can always make a statement with our stunning green leopard print top. Featuring a gorgeous scoop neckline, tie sleeve detailing, and an all-over leopard print, partner this must-have look with jeans to instantly give a casual vibe and sandals for an effortless, everyday look.

If you’re looking for something a little smarter, this party top instantly elevates your outfit for a trend-led look. Made from a soft woven fabric, this top features a stunning halter neck with flattering keyhole back detailing, complete in a swirl print. Finish this look with jeans and trainers for the style you’re looking for.

Shop tall party tops.

Coffee Shop First Date Outfit

Just about everyone loves coffee, if not hot chocolate for sure, and heading to your favourite local coffee shop is the ideal first date to put you at ease. It allows you to spend some quality time with your date whilst in a busy environment. You can always head out on a walk if the conversation doesn’t flow.

You can wear practically anything to a coffee shop, but if you’re after the casual vibe, then you can get cosy in our two favourite outfits below.

Keep cosy and comfortable on your coffee shop date with this must-have balloon sleeve cardigan. Perfect to wrap up in, it features long balloon sleeves and two side pockets. Layer over your go-to casual outfits for the perfect off-duty vibe. We recommend a basic top, light cropped jeans, and trainers for a lighter polished look.

Similarly, as above, the fabric of this cardigan is made from a comfortable knitted fabric, ideal for wrapping up in and an easy way to add some casual vibes to your outfit. It features a trend-led ribbed texture, long sleeves, and it elegantly floats at midi length. Match with a darker wash pair of jeans, crisp white shirt, and a shoulder bag for the perfect casual look.

Shop tall cardigans.

Top Tip: The most important thing you can do or be on a first date is yourself. Regardless of the pressures of outfits, ideas, and conversation starters, simply have fun, as that’s what dating should be about.

Looking for more advice? Head to our tall jeans & a nice top and tall bright clothing collections for more trend-led outfit inspiration.

Found your tall casual first date outfit? Show us how you’re styling it alongside what you get up to by tagging us on our social channels @longtallsallyfashion on Instagram & Facebook by using the hashtag #ImWearingLTS – you might even get featured!