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Home Fashion: Trending What to Wear on a First Date

What To Wear On A First Date

On top of planning, feeling nervous, and getting ready, figuring out what to wear on a first date can feel overwhelming. Do you go all out or keep it casual? Should you wear that new dress or something you’ve had for a while? Luckily, the Princess Polly styling team is here to take one major thing off your to-do list - your outfit! We’ve pulled together our most viral looks and best sellers that will give you cool, calm, and collected vibes. Whether you want to go for something effortlessly cool or a little more elevated, we’ve got loads of outfit inspo to match your vibe. Ready to leave a lasting impression? Find your dream first date outfit below!

Casual First Date Outfits

If your plans are pretty lowkey, an easy, casual first date outfit is for you. One major thing to keep in mind when it comes to all first date outfits, is to wear what you feel comfortable in. Don’t get us wrong, we love seeing you step out of your style comfort zone, but the first date nerves will be high already.

There’s no need to stress yourself out with an ‘out of the blue’ style statement! Plus, you don’t want to be worrying about your outfit when you should be focused on getting to know your date! If it’s not something you would usually feel comfortable wearing, leave it at home.

We have loads of cute, casual and comfortable ‘fits right here. Think easy and breathable mini dresses and laid-back shorts and pants.

Dinner Date Outfits

Plans to wine and dine? If you’re stumped on dinner date outfit ideas, we got you. The classic ‘jeans and a cute top’ combo never fails. It's effortless and gives major "I didn't stress" vibes.

Opt for dark blue or black jeans to keep it dressy, and pair them with a silky cami, lace, or an off-the-shoulder neckline. Throw on some kitten heels or heeled boots and add dainty jewelry for the final touch.

For something a little bolder, try a matching set or a sleek LBD. If you want an eye-catching pop of color (which we honestly love for dinner dates) add a cute red handbag and complete the look with a faux leather moto jacket in the cooler seasons.

When the weather heats up and you need more date night outfit inspo, head to our Summer Date Night Outfit Ideas blog.

Movie Date Night Outfits

A movie date outfit needs to be the perfect mix of cute and comfortable. Go for laid-back vibes with baggy jeans or wide-leg pants - perfect for sitting through those long movie marathons.

And trust us, don’t forget a jacket! You'll want to rug up in your layers once they pump that theater AC.

Off-the-shoulder sweaters and oversized knits are our fave choice for the elevated yet cozy look. Pair with sneakers or chunky boots and throw on your go-to pieces of jewelry for an effortlessly cool OOTD.

Lunch Date Outfits

A cute lunch destination on your schedule? For warmer weather, go for breathable, flowy and effortless styles. A cute summer dress or a top and skirt combo are perfect choices - think Copenhagen-style tops with tie fronts, lace, or frill details paired with denim.

If you’re after something more chic, try a linen maxi dress or a co-ord set. Anything from our Linen 365 collection would make for the perfect lunch date outfit (these styles get bonus points for comfort!).

Crisp white shades with denim or prints like florals, gingham, and stripes always look stunning at daytime events. If it’s chilly, opt for fitted long sleeves, jeans, and a faux leather bomber or an off-the-shoulder knit!

For more lunch date outfit inspo, read our Brunch Outfit Ideas blog.

First Date Tips

Our best first date tip might be cliché, but it’s totally true - just be yourself! First dates can feel nerve-wracking, but wearing something that makes you feel like the best, most relaxed version of yourself is key. Confidence comes from feeling comfortable in your own skin, so opt for an outfit that feels authentically you. Whether it’s your go-to pair of jeans and a cute top, a matching set or a summer dress, the key is to choose something you love and feel comfortable in.

Questions To Ask On A First Date

First things first, “do you like my outfit?” If they say no, RUN! Just kidding, kind of. Keep it light hearted with your first date questions and let your personality shine. Try asking, “If you could have dinner with anyone, who would it be?” or “What’s the best trip you’ve ever been on?” You could also get a little deeper with, “What’s something you’re passionate about?” If you go in with the mindset of being genuinely curious, you’ll never run out of questions.

What To Do On A First Date

Classic first date ideas like grabbing coffee, hitting up a restaurant, or going to the movies are always a win - they're low-pressure and give you plenty of time to chat and connect. Mini-golf is a great way to break the ice and show off your competitive side, while checking out an art gallery or museum gives you lots to talk about. Local Sunday markets are also perfect for strolling and discovering new things together. Whatever you choose, just focus on having fun and getting to know each other!

Come back to this blog whenever you need outfit inspo for your date nights! Find more cute looks like this over on our IG @princesspolly and TikTok @princesspolly.

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