Men’s Style Guide | What To Wear On A Date

You have just asked a woman on a date and you have decided where to go and where to take her. Little do you know that is just half the work. The rest of the work is deciding what to wear! This is your chance to make a good first impression and what you decide to wear, could potentially make or break that (No pressure). Designer Swap is always here to help our clients and we have some ideas on what to wear and will make your life a little easier.

The Movie Date
Although it is going to be dark in the theatre, she will still remember what you wear once you leave. Whether you are going for drinks or just dropping her home it is better safe than sorry so we would recommend you go for a smart-casual look. A look that I personally like is when men wear denim jeans with a plain light coloured dress shirt with a generously sized cardigan. A final touch would be to wear a pair of black dress shoes or black boots. Yes this is a low key date but every little detail counts and I am sure she will appreciate the effort.

The Dinner Date
A way through a woman’s heart is through their stomach. Taking her out for dinner is great, and it’s not just to try the food but to also have good conversation. If you are going to a high end restaurant, we highly recommend that you wear a suit – you can never go wrong dressing like Harvey Specter. No need for a three piece suit but stick to the typical two button suit in black or navy.

If the restaurant is a bit more casual then go for either straight fit beige or denim pants with golf shirt or a navy blazer over it. If the golf shirt is not your style then try the dress shirt and blazer. Finally, I still stick by black dress shoes or dress boots as black goes with everything.

The All-Day Date
This one is a bit of a challenge as there are a ton of things you can do on a date like this. Our biggest suggestion would be to just go casual. Whether it is a day trip to Niagara Falls or you are visiting the Art Gallery of Ontario (AGO), it is better to be comfortable and dress warmly for being both indoors and outdoors. We would suggest wearing a light jacket such as a trench jacket or an unlined parka with a cashmere scarf and leather gloves. While striking a conversation with your date, you will still look great and stay warm.

These are of course just suggestions and they may not work for everyone! But if you really have no idea what to wear, I think it is okay to say that these outfits are a safe bet. She will able to focus more on the conversation at hand rather than the outfit you put together two minutes before picking her up. We hope these tips helped you in making the perfect outfit so good luck, enjoy and have fun on your date!

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Do you have any tips that you’d like to share with us?