Best Outfit Ideas for a First Date

Best Outfit Ideas for a First Date

As a New Yorker who has gone on countless dates, I now can offer my personal advice on what to wear on a first date. In a city where there is a variety of possible date activities, I have acquired copious experience on how to dress according to where your date is taking you. I know all too well the first date jitters that we all feel when trying to pick out the right outfit that will make a great first impression. With my experience in the New York dating scene and my fashion expertise, I finally perfected the art of getting ready for a date. Here are a few tips on how to feel your most confident on your first date:

Going Out for Drinks

In New York City, there are so many incredible bars ranging from sports bars, speakeasies, and hotel lobby bars. With this in mind, you should find out exactly what kind of bar your date is taking you in order to dress accordingly. If you are going to a sports bar, you should keep your outfit more toned down with a pair of skinny jeans and a nice blouse. But if you are going to a speakeasy, you should opt for a sexier look with a silk cami, dark wash skinny jeans, and a pair of pumps. However, regardless of the type of bar, your date is taking you to, avoid wearing a mini skirt. Wearing a dark pair of jeans with a low-cut top is the perfect balance between simple, chic, and sexy!

Day Date

Scheduling a date during the daytime gives you an assortment of activities that you and your date can do. You could go on a walk in the park, go to a museum, or even go biking. Because of this, try to plan with your date the exact activity that you would like to do. However, wearing a chic pair of sneakers or flats with skinny jeans and a more day-time top is a versatile look that can be worn for multiple occasions. For day dates, you want to look like you put effort into your appearance without overdoing it. I know that “athleisure” is on trend right now and make our butts look great but remember ladies, this is a date, not a trip to the supermarket or yoga class! For your date, trade in those leggings and t-shirt for a pair of skinny jeans and a dressier top. Or, if you are going to a museum, opt for a flowy dress with a cute pair of flats! Picking a versatile outfit for a daytime date makes getting dressed easy and simple!

Dinner Date

When going out to dinner, it can be hard deciding on what the appropriate attire is especially when there are so many different types of restaurants. In New York City, what you would wear to a TGIF is probably going to differ from what you would choose to wear to Daniel’s Restaurant. (Lucky you to score that!) So, be sure to ask your date where you are going or how fancy the restaurant is. Planning your outfit for a dinner date is dependent on the atmosphere and overall ambiance of the restaurant. If you have reservations at a fancier restaurant, I suggest wearing a sexy and comfortable dress. However, if your date is taking you to a less formal location, add a denim jacket to your dress to give it a more casual look! In addition, when going on a fancy dinner date, choose to only accentuate either your top or your bottom. For example, if you want to show off your beautiful long legs, then keep your top half and chest more modest. But, if you choose to highlight your top, balance it by keeping your bottom half more toned down. It is all about maintaining a classy yet chic appearance.Remember ladies, you do not want to give it all out at once at the first date. Give him something to look forward to on your next date!

When getting ready for a first date, we have all experienced the feeling of wanting to look perfect but not being able to decide what to wear. Should you wear a fancy dress or keep it more casual with jeans and a dressy blouse? Take the mystery out of picking out what to wear and ask your date what the plans are and where you will be going so you can be prepared the day of. Most importantly, being late is not sexy, most men won’t even notice the extra effort you put in because they are too focused on the fact that you are late. By following these tips, you will always feel confident for your date and make a great first impression!  


2 Comments Add yours

  1. Karyn Von says:

    I love it! Most importantly, be comfortable, relax, & be “YOURSELF.” Eventually, your true colors will be reveal and you want someone to love you for who you are & not for what you are.

    1. modaboss says:

      I’m glad you enjoyed it! and yes! most importantly be comfortable and have fun 🙂

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