Gentlewomxn’s First Date Style Guide

First dates can be intimidating. There’s so much pressure! You have to figure out what to wear, where to go, should you bring your date flowers? Are you meeting there or riding together? Not to mention, your heart AND your mind are racing with anxious excitement, and all of a sudden you have nothing to wear!! Sound familiar? (It’s ok to say yes!) 
Let’s say you know where you’re going, when, transportation, and even the flower predicament. All that’s left is what to wear. You know the outfit has to be perfect, but how do you put together the perfect outfit for someone you’re still getting to know? Do you know what their expectations are? Hopefully you do, but if you don’t, that can make things even more nerve wracking! 
Take a deep breath, and keep reading! We’ve got the ultimate first date style guide below!! 
Style is immensely personal, and everyone WILL have an opinion about it. This is why the very first thing to consider when selecting your first date outfit is what you will feel confident in. There’s nothing more attractive than the glow of pride + confidence someone has in themselves. Plus, this is your opportunity to show who you are. Make a strong, lasting impression on your first date. 
Start with these questions when selecting your outfit: 

  1. What do I want my outfit to say about me? 
  2. What do I need to look like based on where we are going? 

Your answers will be unique to you, and it’s possible your date will have different answers to these questions. That is OK! As long as you dress like you care, you’ll be good to go! Add details that will show your date you put some thought and effort into your outfit. Dress appropriately for the setting, time of day, and atmosphere. This will not only show respect to your date, it can also lay a strong foundation for a long, successful relationship. (No pressure, right?!) 
Let’s get started! 
When selecting your outfit, the first things to consider are the location, atmosphere and time of day of the outfit. You wouldn’t want to wear a three piece suit on a coffee date, would you? ( is the correct answer.) On the other hand, you wouldn’t want to wear a vneck tee with jeans and sneakers to a five star restaurant or the ballet. The weather will also be an important factor when selecting your outfit because you want to feel comfortable throughout your fabulous first date! 
Once you’ve figured out the items above, you can start outfit planning! What’s your favorite style piece? What makes you feel like YOU? Are you ready to rock your classy, new boots or maybe your trendy sneakers? Now’s your chance!!
Coffee, Lunch or Daytime Activity Date 
For these types of dates, you still want to show that you care about your appearance and made an effort to look your best (without overdressing)!  Here are some potential options. 
Tops range from a solid tee to a button-up. Solid is the go-to choice; however, this is your opportunity to say “Hey, this is me” to your date, so wear what feels right to you! If you want to rock your new flannel, go for it!! Or why not wear that short sleeve henley with your bomber jacket you’ve been waiting to pull out of the closet? Polos and short sleeve button-ups may be ok as well, depending on the atmosphere of the location. 
For bottoms, jeans are totally acceptable, but so are chinos and maybe even khakis. For your jeans, opt for a darker wash and (please) no holes! Sneakers, or other canvas based shoes, would be the most appropriate for this type of date, but feel free to dress down your favorite boots!!
Dinner or Evening Activity Date 
There are so many choices for this category as the atmosphere, activity and unofficial “dress code” can vary greatly! Make sure to carefully consider each of these when selecting your outfit because overdressing may lead to awkward or uncomfortable feelings, and dressing too casual may give your date the impression that you didn’t really make an effort. Find that sweet spot in between. 
For a dinner date at a casual or trendy restaurant, tops can include henleys, solid v-neck tees, polos or button-ups. Let’s say you’re going to the hot, new restaurant downtown. A patterned button-up with sleeves rolled up to the forearms would be a great start! Also, much like a day date, dark wash jeans, chinos or maybe khakis are great choices! If it’s chilly out, add a jacket - bomber, demin, etc - or a sweater. Finish your outfit off with fashionable sneakers or top-sliders. 
If fine dining is on the date night to-do list, your outfit will be quite a bit different. V-necks or classic tees are a no-go!! Don’t even look at them for a classy restaurant. Depending on how fancy the restaurant is, this may be a chance to wear a dapper suit. If that feels too dressy, opt for a button-up with a vest, tie, or possibly a blazer. Ditch the dark wash jeans for this type of date, and wow your date with khakis or dress pants. Black jeans may be acceptable, as they are very versatile, BUT make sure they are a good fit for the location and atmosphere. Finally, finish off your outfit with top-sliders, boots or dress shoes.
What's your go-to first date outfit? Share with us in the comments!!