The First Date Outfit

Know what to wear on a first date | Date outfits | feminine style | style advice & tips

When your heart is playing matchmaker, your wardrobe should too. What to wear on a first date is one of the most common questions asked on this blog, and I thought it was the right time I sit down and share my thoughts on it.

As someone who has recently gotten back into the dating game, I know how hard it can be. Put the nerves, the hair, the makeup, and the outfit together, and you’re already flustered enough without adding the boy into the equation, but if my styling skills can help, I’d like to put in my two cents.

What you wear all depends on where you’re going. If your date is choosing and tells you the dreaded, “It’s a surprise”, ask what he thinks you should wear. That doesn’t mean you have to wear what he says, but it gives you a better idea, so you’re not feeling over or underdressed. Like most young people, leaping into the world of dating, going to dinner and seeing a movie is a common occurrence. For this instance, it’s best to wear something smart casual. Depending on your style, this could mean a fit and flare dress and some cute ballet flats or your great slim jeans and a rebellious, edgy biker jacket – but one thing I would steer clear of on a first date is an overly revealing outfit.

Just like the rule: Don’t kiss on the first date; there are rules for dressing for a first date too! If you want that call back from Mr. Maybe, you’re going to need to dress the part.

A first date should be all about mystery. How interesting would an episode of CSI be if we knew who the baddie was in the first five minutes? We’d be flicking to the next channel in an instant and getting through our packet of My Diet Starts Tomorrow Flavoured TimTams much faster than we’d intended.

It’s not about being a prude or keeping your dresses and skirts long enough to stop your most loving friend from pulling out the shotgun; it’s about being yourself and being comfortable in your skin. If you feel you need to show off your body to keep him entertained- you’ve got yourself a date with the wrong person. My simple rule when aiming for the perfect amount of sexiness and style is to pick an area of your body to show off and cover more of the other areas, ie: show off your lovely long legs but choose a less plunging neckline.

The First Date Outfit
Source: Pinterest

The First Date Outfit – Golden Rules

Dress for yourself: Make YOURSELF feel great first because when you feel great, you look confident, your skin glows, and you’re the best version of you. This doesn’t mean that you need to buy a whole new outfit, instead take a little more time getting ready. Don’t rush around trying to make things perfect; things will be perfect on their own if it’s meant to be. Remember that you’re looking for a man you can be yourself around- not a man that you can play pretend with.

Be comfortable: This doesn’t mean your least stained sloppy joe, thongs and a top knot. Think about your outfit options, while a tight fitting dress may have sexy dripping all over it; if you’re shifting in your seat or pulling it down all night- it’s not the best choice. Save that for the evening you plan on having him take it off you.

Let’s talk about shoes: Those red platforms might be hot for a night out with your girlfriends, but nothing is more of an eyesore than a woman who can’t walk in her heels or someone with sore feet that you just want to offer a pair of slippers to! My rule when buying heels has always been, don’t buy them if you can’t run in them.

Be yourself: If you’re a jeans and sneakers girl, own it! He accepted this date for a reason and dressing up in that mini skirt and sequin top is false advertising. He came for you, not the girl under all those sparkles!

Don’t Buy A New Outfit: Think about wearing something you already own to the date. Buying something new can backfire if the date doesn’t go so well, you’ll feel like you’ve wasted your hard-earned money. If you have to buy some new dresses or clothing, actually consider the outfits wear purposes before investing.

What To Wear On A First Date – The Casual Coffee Date

The First Date Outfit - What To Wear On A First Date - Alarna Hope Fashion Stylist
Source: Pinterest

A daytime date I’ve done plenty of times is the coffee date, bonus points if there’s cake involved. A coffee date is meant to be casual, so in winter, a pair of jeans and a knit or long sleeve top could work with a cute scarf or in summer, a sundress or maxi dress will suit the occasion. Flats or shoes with a small heel will work best, particularly if you live in the city. It may lead to a little stroll afterwards, and blisters just don’t work with many outfits.

You want to go for an effortless vibe, so if you get stuck before the date, the day doesn’t go as planned and you’re in a hurry to get out that door – neutral colours like black and white always work. Add a touch of fun with simple accessories so you can have that ‘I just woke up looking this good’ thing going on.

Wear Appropriate Makeup: While a date calls for a little extra effort, remember it’s daytime. Nighttime makeup is a little darker, and daytime makeup is a bit more natural. Make sure you haven’t got any foundation lines and kept it simple.

What To Wear To A Dinner Date

The First Date Outfit - What To Wear On A First Date | Alarna Hope Fashion Stylist
Source: Pinterest

When it’s a dinner date, always research the restaurant. If you haven’t been there before a handy little trick you can do is jump on the restaurant’s Facebook page or Instagram and have a look for tagged photos or check-ins. You’ll likely find pictures of people there, and you can get a rough idea of what’s acceptable attire. The last thing you want is to wear something completely over the top to a hole in the wall cafe.

The Fail Safe Option: There are three ways you can make your outfit fail safe for a dinner date:

1. Wear Separates: It always helps to make you blend. You could wear a silk shirt with a pair of soft pants and heels and be ready for a nicer restaurant or a small cafe.


2. Nude Shoes: These don’t stand out but give you a nice touch of height. A nude shoe makes your legs look miles long, and they go with everything except dark stockings – don’t do it.

3. Thin Knits: Hallelujah for these inventions, a soft knit paired with anything but denim can help to ensure you don’t push the boundaries of a dress code or a surprise date destination. There’s a perfect combination above, or you could try a leather pencil skirt, a soft pair of trousers or even a cute fit and flare skirt. Add some accessories and nude heels to step up your look and hot damn, you are ready to date!

For all the Effortless Bitches out there, what did you wear on one of your first dates? Paint me a picture with your words in the comments below!



  1. Avatar for Daniela King

    Thanks for sharing! The key is not to stand out too much but look cute.

    1. Avatar for ALARNA HOPE

      Exactly! Good luck on your date! x

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