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What to Wear on the First Date

February 12, 2021

Tips for your first date outfit

Below, we share thoughts from the Waer team about what to wear on your next first date. No matter where you go, we've got you covered.

First dates can be wonderful and important to the future of a relationship. But under the bright exterior are the butterflies in our stomach which signify both excitement and our desire to give off the best possible first impression. In addition to choosing the right location for the date and the right topics of conversation during the date, a key factor in our ability as men to get a second date is a great appearance!

Clothes do not make the man, but when you think of James Bond your mental picture undoubtedly includes his wardrobe. Therefore, it is absolutely essential that what we wear reflects our personality and makes us feel comfortable. Self-confidence and how we portray ourselves play a key role in how our date will perceive us!

It is important to pay attention to the details: make sure your clothes are well-ironed, your button-down is properly buttoned, and your shoes are well-polished. This will give you the image of a man who respects, loves and takes care of himself. That being said, the outfit you choose for your first date should reflect the time and place of the date. You want to stand out for the right reasons, and being out of place because of your attire is not the way to impress. The right accessories can also be helpful in highlighting your outfit. A nice watch and a little cologne can go a long way.

Depending on the nature of your first date, we recommend the following outfits:

What to wear on a casual outdoor date

As we head toward spring and global lockdowns (hopefully) begin to ease, more and more dates will likely be some type of outdoor adventure. If you are planning to visit an outdoor locale for your first date, choose something that exhibits both elegance and comfort. You’ll want to be comfortable for your walk and can do this in a classy way. A pair of well-tailored shorts and a nice sweater or t-shirt should do the trick. You can also go for a pair of well-fitting sweats.

What to wear on a casual coffee date

If your first date is a casual coffee, be it in the morning or the afternoon, a casual, chic style is the way to go. Consider a pair of soft moccasins or cool sneakers, a statement t-shirt, or a button-down with a zip sweater. Depending on where you live, you can also get away with a casual jacket for that extra level of elegance.

What to wear for a lunch or dinner date

If your date includes food, the outfit you choose should inspire you with confidence and reflect your charming personality. Chinos are one of the most tried and tested options, as they can be dressed up with a button-down shirt or down with a cool sweater. We recommend avoiding a hoodie for a dinner date, as it can be overly casual and give your date the wrong impression.

First dates can certainly have awkward moments, but with our tips you can all but guarantee that your clothing choice is not one of the awkward factors. Remember, the whole point of your date is for you and your date to feel comfortable, get to know each other, and have a great time. Don’t overthink it, just follow our suggestions and you should be good to go.

Clothes that match well

Waer makes sure you always have the best suggestions in the closet, so that you feel great every time you leave the house. In order to help men everywhere look and feel their best, we offer free shipping on all orders in Cyprus and on all orders over 150 Euros worldwide. Our team is always here to answer your questions and we would gladly give you personalized fashion advice. Feel free to email us at or DM us on Facebook or Instagram.

Written by Waer Clothing

The company re-imagining men's fashion.

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