What to Wear on a Date: A Style Guide for Men

Your clothing is an extension of yourself, your own personal branding. This piece won’t tell you exactly what to wear on a date, but will give you a shove in the right direction to make sure you’re giving off the correct impression when you dress up for that all important first encounter. They’re making an effort, you should too. Let’s begin.

1. The Suit: Yes or No?

The only correct response is: it depends. Are you going to Eleven Madison Park?  Then yes, by all means get dressy. Are you going out for a casual drink? Leave it at home. For the most part looking like you walked out of an episode of Mad Men can be a bit too much. Make your date feel relaxed by exhibiting it yourself. Suits can be uptight if you’ve misjudged the setting.

What to wear on a date - Men's Style Guide

2. Keep It Smart

If you’re forgoing the suit it doesn’t give you an excuse to look disheveled. Collared shirts, flecked wool pants and chelsea boots will be sure to give off the right impression. Make sure the shirts are pressed and clean, and the shoes buffed. Be a man who takes pride in his appearance, looking smart also shows your date that you take her seriously, and want to look good for the occasion. If you feel uncomfortable in a shirt and want to try something a little different, substitute the shirt for a turtle-neck for the perfect blend of smart & casual.

3. Be Well Groomed

Shower. Trim your beard or shave that stubble depending on what you’re most comfortable with. Chances are you already have an established hairstyle so stick to that, don’t get experimental right before your date. If your nails are ragged, clip or file them down. These are all things that will be noticed.


4. The Scent

Now that you’re groomed to perfection it’s time to pick your fragrance. It’s important to understand what skin type you have, as this will affect the fragrances volatility. For oily skin an Eau De Toilette will provide a long lasting scent, but may be too irritating if your skin is sensitive.If you do happen to have sensitive skin pick a scent with a low alcohol content. Giving yourself a rash before your date would be a nightmare. Take care when applying, if you are overly familiar with the scent of your cologne you may end up underestimating how strong the smell is. Keep it to 2-3 sprays maximum. Don’t go into your date smelling like a high school locker room.

Final Thoughts

It’s important to take any and all guides telling you what to wear on a date with a pinch of salt, even this one. These tips will provide you with a good foundation on how to make a good impression through what you wear, but nobody knows your own style like you.

Bottom line: Be comfortable and feel confident.