What To Wear - First Date Outfit Checklist | CLiKD Dating App

What to Wear – First Date Outfit Checklist

  • Closeup of woman holding shopping bags

    Meet/Eat/Love (MEL) #4

    So it’s happening, you’ve matched with someone that you ACTUALLY want to take the conversation from online to offline with. No more endless texts and pic swapping, you will actually be meeting each other IN PERSON!

    In. Real. Life. Like actually sharing the same air space.

    Mind. Blown

    You’ve agreed on a date, time and place, then this pops into your head, “What to wear, what to wear…. WHAT TO WEAR FOR THAT FIRST DATE?!”

    Scenario 1

    Will you try on 10+ outfits then send ‘First Date Outfit’ snaps to your bestie for her input? What about this? What about that one? Too slutty? Too conservative?


    Scenario 2

    Will you be a calm cool chic because you’ve read the First Date Outfit Checklist below and you’ll know what to wear for your first date.

    Looking into a girl's revolving wardrobe

    I like to call it a First Date Outfit CHECKLIST because First Date Outfit RULES just sounds so authoritative, plus aren’t RULES meant to be broken anyway? 😉 Also, First Date Outfit TIPS just sounds so Martha Stewart. Checklists, however, sound more effortless, something you can easily run through to help you find your First Date Outfit. The checklist is also short, as it’s meant to make your life simpler, not more complicated. Who has time to go through a gazillion checklist questions to figure out what to wear?


    After over 20 months of online dating now, I’ve been caught wearing the wrong outfit for the date OR been super judge-y of my date’s outfit (*but only to learn there’s always a great story behind every loud shirt, see below.)

    I’ve shortlisted FOUR simple First Date Outfit Checklist questions to help you find what to wear for your First Date; some inspired by my own real first date experiences, others are just being practical.


    First of all, it’s a lot easier after you guys both agreed on the First Date activity, so you can limit down the universe of your wardrobe to what’s activity appropriate.

    Real first date experience: Matched with Mr. Flamenco in Seville and we agreed to meet at Triana Bridge. He was dressed in a white button shirt and trousers. I was dressed in jeans shorts cut-offs and a black tank top. This was middle of August after all! Oops, I guess agreeing to meet at the bridge was too vague for the rest of the evening’s activities. After we met, Mr. Flamenco took us to a local spot, next to the bridge, famous for their gourmet Spanish conservas (aka. canned foods) and sampled delicious tuna, anchovies, peppers, and sardines. Afterwards, we heard loud music and laughter nearby. It led us to a restaurant down the street with a packed crowd, dancing impromptu flamenco. So freakin’ awesome! It turned out to be a pretty fun packed night and I guess we both ended up wearing appropriate First Date Outfits after all.

    Triana bridge

    Triana bridge


    Have you ever tried on a shirt, shorts, jeans or dress and all you could do was hold your breath and tried not to sit? If you can just suck in our stomach for the rest of the night, you’ll be fine right? I like to choose outfits that don’t make me feel like a stuffed sausage, an outfit that I can breathe normally in, without having to hold my breath or suck in my stomach.

    Dancing sausage

    Trust me, no matter how awesome you think you look, you want to be able to share a laugh without worrying you’ll pop off your jean’s top button, sit at a bar without worrying your zipper will burst and dance the night away without the seams ripping.



    I know you’ve been dying to wear your killer heels, but remember what happened last time? Remember her?!

    Girl with bags on feet

    Source: https://www.buzzfeed.com/juliareinstein/who-is-the-burger-feet-girl?utm_term=.ehpvzQmXD2#.lpr7Qjqe5v

    You want your feet to be comfortable too. Otherwise, you’ll be grinning through seething teeth as your date asks if you wanted another round of drinks or wants to dance the night away.



    Confidence goes a long way when making a great first impression. That’s why when choosing your First Date Outfit, you should feel like you are the ‘hottest/coolest/hippest/nerdiest/whatever identifies you’ person ever.

    Real first date experience: There was Mr. Belgium in Barcelona. We matched and decided to grab brunch. I was wearing my usual jeans shorts cut-offs and blouse. Mr. Belgium arrived earlier than I did so when I walked to where he was seated, the first thing I saw was his *loud shirt. He greeted me with a warm smile but I could not stop staring at his shirt. It was definitely on the loud and colourful side, like a lava lamp.

    Lava lamp - play doh

    He tells me, during brunch, it was his lucky shirt from the past 8 years. Whenever he wears it, it puts him in a good mood because of how colourful it is, and being in a good mood makes it easier to feel confident too. It rubbed off on me and put me in a good mood too! Who knew First Date Outfits can have double duty?

    So that’s it! It’s FOUR very simple and short checklist questions for what to wear on your first date. If you’ve answered YES to the above (minus the first question as that’s not a yes/no question lol), you my friend, have found your First Date Outfit.

    Have fun on that first date!

    Ms. Mel

    CLiKD, Creative Dating App - Don't Just Date Anyone


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