Best Outfits to Wear for Dates

Dating In The 6ix Jun 10, 2020

Fashion is complicated. The rules of no wearing white after Labour Day or saying no to yellow in the winter can make dressing up a task and a half. But you and your boo don’t have to fear because the fashion police won’t come here, cause we’re gonna take a look at the overall do’s and don’ts of fashion, in this date edition.

Outdoor Activities

If you and your boo are all about smoothies and kale, there is no reason you can’t look good doing it. If you’re looking for a more feminine style, one option is a tennis skirt with a tank top tucked in. Whether you wear a black or white skirt with a colourful top, or vice versa, this is one look that will get everybody staring. If skirts aren’t your thing, and you still want something if a similar style, then replace the skirt with shorts, and you’re good to go. One last option would be to wear leggings with a sports bra, the colour of your choosing. These are all excellent options, as they are flattering from all angles and won’t make you feel like you’re wearing clothes with extra weight.

If you’re looking for something a little more masculine, some shorts and a t-shirt or a muscle tee work excellently. They show off the right features while still being light and proper apparel for a hike. The best part here is that you can mix and match to see what feels the most comfortable, which makes it all about your personal preference. When doing some athletic activity, it’s all about vibrancy. Go grab some dark with some light or go all out with the colour to look amazing on your hike.

Pool Side

Kicking it pool side with a cocktail while soaking up the sun is a classic summer activity no matter if it’s sunrise or sunset. A feminine look is dependent on your preferred bathing suit style. For a bikini or a tankini, some shorts and a cute t-shirt or a t-shirt dress are the perfect way to go. For a flattering bathing-suit, you need a flattering “cover up” to show off the curves and toned muscles. For a one piece, a sheer or almost see through dress is definitely the way to go. Paired with some fancy flip flops, this is a fashionable yet comfortable choice that will get everyone copying your style. These two options also serve as a bonus for being perfectly fashionable for the nighttime, as these pool parties can go all night.

If you’re looking for something more on the masculine side, swim trunks and a t-shirt is the way to go. Bright coloured swim trunks with a neon coloured top are the perfect way to get people’s attention and come dressed to impress, but if you’re feeling a little frisky, going shirtless with a towel draped around your shoulders is also an option. Just pack a light long sleeve T for when the nighttime hits. The key here is all about looking cute and wearing something convenient, so whether it’s a bikini with some jeans or some trunks with a muscle tee, you’ll have a blast and look cute doing it.


Brunching is not only an elevated breakfast experience, but a way of life. Anything that can support drinking Mimosas at 11:00am is a win in my books. But the true question is what to wear for something that is one of the best options for a first date or for any date. For a feminine vibe, I would recommend some ripped jeans with a cute sweater or top. If you’re feeling like being a bit more on the dressier side, then a simple black or brown skirt [depending on the season] will do the trick. Pair it with some sneakers or booties to complete this look and you’re good to go. This is a sure success for brunch because it’s cute without being too much.

For something on the masculine side, jeans and a sweater or a t-shirt will definitely do this date justice. Put on your favourite pair of sneakers or some Timberlands to feel even more confident. Brunch is all about food and getting to drink before 5:00pm [on a good day], so don’t stress about your outfit too much, as the vibe here is all about being cute ‘n’ casual.


For a classic dinner date, for a feminine touch, a nice dress or a nice romper will do the trick to make you a classy and fashionable date. Depending on the season, you can wear black, white, or a colour that compliments you and makes your features pop. Add some heels, to dress it up, or some wedges to dress it down, but no matter what, this is a classic and classy option.

In terms of a more masculine option for dinner, a dress shirt or a “fancy” sweater with black jeans, fills the bill depending on the place, of course. Dress up this outfit with dress shoes or keep it more on the simple side with black boots or boat shoes, if it’s summer. Dinner is a time where it’s about the food, company, and the ambiance, so your clothes matter, which is why this outfit never fails, because it blends in no matter where you go and can make you feel like a million bucks.


When it comes to picnics, the goal is to avoid a fashion mishap. Dressing in a masculine manner is easy, in this case, but dressing in a feminine manner is hard. Dresses or skirts can lead to Marilyn Monroe moments and do not allow you to sit comfortably, so if you’re looking for a feminine option, then some shorts with a crop top or shirt with some plaid tied around your waist is a great way to be cute yet confident for this one-of-a-kind date idea. If you’re looking to spice this up, wedges or booties will do the trick, but if you’re looking for a simpler option, then  sandals or sneakers are the way to go.

For a more masculine look shorts or jeans and a t-shirt with a jean jacket will do. Picnics are all about simplicity so there is no need to fuss.

Because picnics are a spring, summer, or early fall treat, then color is important here. For spring, pastels (light pinks, purples, blues, and greens) are a great way to dress to complement the season. Similarly, for summer the same colors can be used just in a more vibrant way – think neon and bold instead of pretty and pastel to make summer have nothing on you. For fall I’d recommend some deep reds or oranges as a great way to welcome the season.

Parties/Late Night Dates

When it comes to parties and late night dates, dressing properly is important because everyone will be staring whether you like it or not! For something feminine, anything in the shade black goes, but I would recommend different outfits depending on the season. For fall and winter, black jeans or a fitted skirt with a cute top is definitely the way to go. Stick to the reds, burgundies, oranges, etc. to make yourself feel right at home with the season of pumpkin spice and everything nice. For a more springy/summery vibe, shorts or light washed jeans will definitely do the trick, as most events will be outdoors or on a patio. Pastels and bright colors will also be your best friend to keep everyone’s eyes on you. Whether you tie this look together with some short boots, wedges, or sandals, you’ll feel like the two million bucks you deserve.

For a more masculine touch,  black jeans with a sweater or a loose dress shirt is 110% the way to come dressed to impress. Pair this with boots or boat shoes to elevate this outfit to 120%. The key to a more masculine style is to keep it simple yet fun. Explore the right colours for the right seasons and you’ll be sure to make all the heads turn your way. For the fall, keep it cool with reds, browns, or dark greens, whereas for the spring/summer, the focus should be on the blues, greens, and purples because they are always a hit.

Going out is all about making a statement on the fashion front, so come prepared to get stares. These types of social events are designed to make you feel glamourous while dining or drinking, so pull out some of your favourite clothing items that make you feel 2x as confident as you normally do, which should be the norm all the time, and rock it.

I hope these fashion suggestions help cut down on your closet melt downs and last-minute shopping sprees because, let’s face it, we’ve all been there. It’s not fun having a melt down with your makeup on in your closet an hour before a date is coming to pick you up – it adds to the pressure of wanting to look your best and creates more stress. With that being said, the key here is to dress up and dress you. Don’t be scared to add your personal style to the mix and rock each outfit with confidence.

As always, stay healthy and safe.



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Hi! My name is Maya Leah, I am a twenty year old theatre student at Queen's University. I am a Netflix binger, bruncher, and Jesse Eisenberg obsesser who enjoys curling up with a good book...

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