How to Dress on a First Date

The first date can be nerve-wracking, especially when you’re trying to decide on what to wear. You don’t have to splurge on a new outfit at the mall or get expert style advice, just follow my tips and you’ll have her wowed at first glance.

Thankfully, none of these suggestions are difficult to implement. They just take a bit of planning and self-reflection. Well, and maybe a *little* bit of shopping if you haven’t touched your wardrobe in years.

Dress Your Style

While it may sound trite, you need to dress as a reflection of you. The first date sets the tone for the rest of the relationship, so if she doesn’t like how you dress or your style, you need to know up front and not later. If you’ve never stepped foot into a pair of khakis, then don’t wear them. Bring your own unique sense of style into the little things, like your shoes.

A nice pair of PF Flyers are comfortable to wear and are unique enough to show her that you have your own flair. The point isn’t to look like everyone else, quite the opposite. Unfollow the crowd and bring your own style to the table.

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Be Comfortable

You don’t want to constantly be twitching in your seat because you wore the wrong pair of underwear or an outfit that doesn’t fit right. Avoid wearing anything that will need to be adjusted, and aim for clothing that fits right and doesn’t chafe or ride up. Your date will notice if you’re uncomfortable, so just try to avoid it at all costs. I once wore a pair of shoes with a hole in the toe on a date. Please don’t do that either. My toe got wet, which wasn’t comfortable, and I probably looked pretty silly too. If only I had thought to bring my PF high tops. 

Consider the Activity

You don’t want to wear a suit if you’re just attending a movie, so be clear on where you guys are going on your first date. If the activity is outside, dress for the weather. A nice pair of jeans dressed with a nice top is usually the best bet, but you ultimately need to assess the situation and activity before searching your closet. I keep mentioning shoes because they’re important and sometimes given little thought when you’re in a rush. Don’t wear dress shoes if you’re going to the beach, or flip-flops to a fancy dinner. I’m a big fan of PF Flyers for their versatility, and I’m sure you have some favorites too.

Don’t dress for the office

There’s a difference in dressing for a date and dressing for work. Avoid khakis and striped, collared shirts and go for something more trendy and stylish. While your work may not appreciate your personal style, your date will. Much like the office, you don’t have to style your hair the same way either. Go bolder and just be yourself with the style you want to show off.

Remember the Little Things

man-wearing-pantsThere’s more to an outfit than just shirt and pants. By paying attention to the details, you’re showing your date that you are detail oriented in life. Add accessories, such as a watch, tie, cuff links, or a nice pair of socks. You may think she won’t notice these things, but when she does, it’s only positive for you. Once you’ve set the basics and the extras, you need to remember to have your outfit cleaned and wrinkle free. These details are noticeable, so if the clothes you are going to wear have been sitting in the back of the closet for a year, take an iron to them before you put them on.

Make sure your shoes are clean and the laces aren’t dingy, because all of these are things that she will notice and they show her exactly how detailed you are in your life. Once you’ve got these covered, you’ll be relaxed on your date knowing that you did everything you should have for your clothing choice. Once you’ve set the basics and the extras, you need to remember to have your outfit cleaned and wrinkle free. These details are noticeable, so if the clothes you are going to wear have been sitting in the back of the closet for a year, take an iron to them before you put them on.

Make sure your shoes are clean and the laces aren’t dingy, because all of these are things that she will notice and they show her exactly how detailed you are in your life. Once you’ve got these covered, you’ll be relaxed on your date knowing that you did everything you should have for your clothing choice.

Check out PF Flyers on Tumblr and shop now if you are convinced these will help you on your first date.

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Jason Batansky

Jason Batansky, a 34-year-old entrepreneur/blogger, has built three successful online businesses, granting him the freedom to travel and work remotely across South America, Southeast Asia, and Europe. Currently residing in Miami Beach, Jason thrives on the challenges and rewards of his dynamic lifestyle.

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