What to Wear on a First Date | 6 Outfits, 6 Occasions

Firstly, yes girl! Go get that date! Secondly, you look amazing anyway and he/she/they know it so stop stressing about all the little details and go enjoy yourself!

That being said, of course you want to look absolutely perfect for them so that you can make a killer first impression. You also don’t want to have to stress about whether you’re dressed for the right occasion or if your outfit was the right choice and you especially don’t want to stress about being uncomfortable or having to suck in your stomach all night (just let it all out girl, there’s no need for that).

So there’s a few categories and suggestions I have for different types of dates. Let’s go through some of them –

  1. The Casual Dinner Date/Movie

I’m personally not a fan of movies for a first date because you don’t get to talk to your date! Although it does make dressing easier when you’re both in the dark for about 90% of the date. However, it’s more likely that if your Boo is a gentleman or a lady they’ll probably take you to dinner first/after/instead of.

My SuggestionCowl Top in Wheaton, black skinny jeans, black ankle boots and the Twist Pearl Earring.

My Reasoning – The Cowl Top is such a simple, minimal but flattering choice for a casual dinner. It shows just a tiny bit of skin to leave ‘em guessing but not too much. When it’s paired with black skinny jeans it sits on the border of dressy but also casual so it’s appropriate whether they take you to the local sushi joint or to a fancy Italian restaurant. Boots add a little bit of an “edge” to the outfit so it’s not too refined and elegant and the Twist Pearl Earring is a simple, non-distracting final touch.

  1. The Fine Dining Date

Wow, look at you lucky lady – fancy dinner for the first date?! It’s hard to know how formal to go when they take you to a nice restaurant but I always find it better to dress up than to dress down. Fine dining isn’t just about the food but about the atmosphere, the presentation and the overall experience. Part of that experience is the feeling of luxury, sophistication and being chic. Your date likely is taking you there for that experience to make themselves appear more sophisticated and worldly (or show off their money but yuck no one likes that), you should try to reciprocate the sentiment with your outfit!

My SuggestionCurvature Dress in Merlot, nude stiletto pumps, Tear Drop Pearl Earring.

My Reasoning – CURVES! The Curvature Dress was literally designed for one purpose – to highlight the best of a woman’s curvaceous body. Your date is making the effort to take you to an expensive restaurant to really impress you on the first date, it’s not necessary for them to do but it’s still so nice of them. Make an effort yourself and put on something with a real oomph factor to it and make yourself the standout gal in the room.

The Curvature Dress in Merlot is a great choice because the Black might be a little too dressy for dinner but Merlot looks great on everyone and is slightly less formal. With a pair of heels, you’ll lengthen your body, your legs will look more toned and your booty will stand out (heels cause your lower back to arch slightly making your butt look amazing)! The Tear Drop Pearl Earring is the final touch, adding something elegant but detailed to show that you really thought carefully about impressing them the way they tried to impress you!

  1. The Sports Game Date

So. Much. Fun! This is a pretty “masculine” date so I like the idea of dressing a little bit more feminine but casual to impress my date but also not look silly for wearing a cocktail dress to a hockey game. Your outfit should be practical but also look like you put effort into it because you’re not just hanging out with the “bro’s”, you’re on a date!

My Suggestion – Plain white t-shirt, Origami Skirt in Stone OR Black, white lace-up sneakers and a sports cap of your favourite playing team.

My Reasoning – Feminine but not silly. The plain t-shirt makes the outfit more casual but the skirt shows that you’re still putting an effort in because it is after all, a date. Tuck the t-shirt in loosely to your skirt to show off your figure a little bit and wear sneakers to dress it down but also because stadiums have stairs and you don’t want to do those with heels on at a sports game…especially when you’re helping them carry hot dogs and drinks. The sports cap is there because where’s your team spirit?!

  1. Hotel/Rooftop Drinks

This is my personal favourite for a first date. You have the atmosphere, the sophistication (without the pretentiousness), an excuse to dress up but not the pressure to be overly dressed, you have the booze to make conversations less awkward and more fluid and also – bar snacks. I hate not having the option to get something to graze on when I’m drinking but most hotel/rooftop bars have a small menu of appetisers. J

My SuggestionOrigami Dress in Black OR Stone, sandals or heels depending on your mood/the vibe of the bar, a light cardigan because rooftop bars can get chilly.

My Reasoning – The Origami Dress is a simple and easy solution especially if you don’t have much time to change after work or if you’re going straight from work. It’s cute and flirty without being too “dressed up”. If you pair it with sandals it looks even more casual and gives off a “oh this old thing? I just threw it on but I’m effortlessly glamorous” type vibe. It fits well into any nice bar environment and you won’t ever be over dressed or under-dressed. Like I said, it’s also work friendly so you can wear it straight from work or from the bar to work the next day ;).

  1. Coffee/Brunch/Lunch

Brunch is honestly my favourite meal/activity. I love to really research menus before I go so I don’t get stuck making bad decisions on what to eat because I’m too busy talking! It’s also such a great first date because it’s in the day time so you can see and hear your date properly, you can have coffee to get your energy levels up and also there’s food in case you need a moment to think about something to say. It’s also a super happy activity – I don’t know anyone who isn’t happy when they brunch and it’s nice to be out in such positive environments on a first date.

My SuggestionLotus Drape Top in Bloom, blue skinny jeans, ballet flats or sandals, Floating Pearl Ring.

My Reasoning – The Lotus Drape Top is a really bright but cute top to wear in the daytime, it stands out without being too dressy, has a cute little scoop back and front cut-out to show off a little skin and the asymmetry makes it flirty and young. Pair it with blue skinny jeans and flat shoes to make it more of a day-time casual type look. Finish off the look with the Floating Pearl Ring which adds a little bit of personality and detail to your look without being over the top for the day time.

  1. The Outdoors

Sorry, can’t really help you there because I’m not a big outdoors gal. What I will say though, is that when in doubt – leggings are practical, and they make your booty look great! And comfortable sneakers because you don’t want to be that girl that wears sandals or heels to a hike.


In any case, whatever you wear you’ll look great as long as you wear it with confidence! Don’t fidget with your outfit, own that look and good luck with your first date! Let me know how it goes and what you're wearing to your date in the comments below!



You wrote this blog very well. Very knowledgeable. Thanks for sharing this

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