Dressing for a First Date! - HALFTEE Layering Fashions

Dressing for a First Date!

Let’s talk first dates!

First dates are exciting but nerve-wracking. All of the expected questions arise…

What should we do?

Who is paying?

What will we talk about?

What should I wear?


But, of course, my favorite of those questions is “What should I wear?”


Let’s break this down into a few different categories of dates: fancy, casual indoor, casual outdoor, and water activity.



Fancy Date

            Fancy dates can be extra stressful, especially if you do not dress up much. One of the most common fancy dates is a nice dinner. I love to pull out all the fun closet pieces I don’t get to wear on any other day. I love to wear my heels and grab a fun purse. Heels can be dressed up or down depending on if your date is more fancy or classy. Heels with a dress gives way to a fancier look, but heels can also be paired with white jeans or slacks and a nice blouse to create a more balanced look. Heels can be paired with a sundress which is more casual as well. One tip is to not wear heels that are going to hurt your feet or get uncomfortable throughout the night; stick to short heels that you have broken in.




Casual Indoor

            There are several different activities that would fall under the casual indoor date category. One of the most common is going to see a movie. I don’t know about you but I personally I like to dress comfy for a movie. This is probably one of the only dates that you can and SHOULD dress down for. You do not want to worry about feeling overdressed. This is where I would bring out the sporty look. Cute leggings or biker shorts with a comfy top. Movie theaters often get cold, so I like to bring a jacket or wear a vintage sweater to prepare for this.

            For other casual indoor dates, I would suggest a pair of jeans and a casual, but stylish top. You want to avoid looking sloppy, while also not overdoing it. Jeans and a statement top allow you to look as though you are put together but not trying too hard. This is also a good time to bring out the sundresses. Sundresses are comfy but look clean and chic. Indoor dates are a better option for sundresses because there is no need to worry about the wind blowing your dress up etc. that would come with an outdoor date.




Casual Outdoor

            From mini golf to a hike, to an amusement park. There are so many outdoor dates options. This is where I am pickier with my shirts. I know the nervous sweats are going to come combined with being outside which means I MUST pick a sweat proof shirt. This is where I might wear a cute oversized graphic tee with jean shorts, leggings, or biking shorts, depending. There are so many different graphic tees, but a lot of times they have a band or artist as the image. This is a great conversation starter and something your date will likely comment on. I love to wear lifestyle sneakers here that are comfy but stylish since there will likely be some walking involved. Another alternative here is a jumper or romper. Jumpers/rompers can be dressed up cute with a graphic tee or halftee underneath and they bring extra comfort for an outdoor activity, especially compared to denim. 

            There is an extra layer to unfold when dressing for outdoor dates… weather! It is super important to check the weather or remember what season it is. If it is winter, you will want to pull out the layers and the puffer coats. Beanies and cute boots can add spice to an outdoor winter fit. In the summer you want to keep it light and airy, and avoid colors such as light grey that sweat will show more in. Prepare for rain with a cute raincoat or bring an umbrella. Avoid white at all costs when rain is on the forecast!!




Water activity

            The last category we will cover today is water dates. This could be going to the beach/lake, kayaking/canoeing, waterparks, hot tubbing and more. I like to wear a swimsuit that I know I feel comfortable and confident in. I know lots of us might feel a little conscious being in a swimsuit on the first date, so you want to choose one you know you love on yourself. I would suggest finding a mid-coverage swimsuit, at least for a first date. We do not want to wear something that is going to ride up or require a lot of adjusting. I would also avoid white bottoms. Depending on the activity, the water might be dirty, and we do not want to ruin our clean white bottoms.

            For coverup I would wear something simple that won’t be uncomfortable to put over a wet swimsuit. I personally like to wear a small dress over my swimsuits. Easy to put on over and take off. Another option would be a tank or t-shirt with athletic or comfy shorts. Don’t forget a towel and sunscreen!! Wear minimal makeup if needed and make sure its waterproof; we don’t need black streaks running down our face!


A few more general tips!

I love to bring out my statement jewelry which adds to any look as well. Chunky hoops and bracelets, or a watch can make a casual outfit appear to have more effort.

Crossbody bags are awesome because they are cute and convenient. They are the perfect size for anything you need to bring such as a phone, wallet, or lip gloss. They are super trendy right now too, which is a bonus.

            Overall, you want to be you. Dress in an outfit you know you love and feel confident in. Stick to your style and don’t experiment too much on a first date. Wear what you love, and you will be relieved to not be worrying about your outfit once you are on the date!


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