What to Wear on A First Date (The "Non-Cosmo" Version)

First dates can conjure up so many different emotions, you could be excited, happy, nervous, anxious, all of the above... Whether the first date is with someone you met online, or you’re back out on the dating scene after a divorce, or you’re meeting someone your parents set you up with, figuring out what to wear on the date doesn't have to be stressful. In this edition of “what to wear when” we’ll be talking about how to dress for a first date so that your outfit can communicate your personality. No fluff about what you MUST wear to impress your date or the top trends you SHOULD be wearing on a date- Just tips on what you can do to put together a first date outfit that represents you. 


Does what you wear on a first date matter?

Aah, the age old question, does what you wear really matter? As you already know from my “What to wear on an Interview” post, it takes just 7 seconds to make a first impression. Whether we like it or not, one of the factors that influence a first impression is attire. In other words, a person (an interviewer, a date, someone you bump into on the street, etc.) will make up their mind about the type of person you are based on what you’re wearing (among other things).

Now, you may be thinking, “If first impressions matter, then I need to wear something that's trendy on a first date.” Well, not if it doesn't represent you. What you wear (and how you wear it) gives visual cues to the other person about you. Your style is an extension of you, it represents you.  If you have a classic personal style it really won’t make sense if you show up to a date wearing a mini skirt, stiletto heels and a bright top just because it's "fashionable". Probably an a-line skirt and a belted cardigan may work better… When choosing your first date outfit, remember that first impressions count so make sure your outfit represents you and makes you feel great and confident. 


Pre-date checklist

OK, so we’ve got that what you wear on a first date should represent you.  Perfect, now where do you from here...  Here are some things to keep in mind when choosing a first date outfit.

  •  Find out where you’re going on the date and dress appropriately- If you’re planning the date, you’ve already got this tip set. If you’re not, just ask. You don’t want to show up over or under dressed. 
  • Make sure what you are wearing is comfortable- If you decide to shop for a new outfit make sure you wear it before your date- especially a new pair of shoes!! You definitely do not want to be thinking of the newly formed blister on your foot while you’re on your date and then implode when your date says “I’m having a great time, how about we walk around the neighborhood”. 
  • Check the weather- When you look at the weather forecast and it says 100% chance of thunderstorms it’s probably not a good idea not to wear that white linen dress and open toe sandals that you were planning… Be prepared and choose an alternative outfit in case of bad weather.


First Impressions matter- got it ; Pre-date Checklist- got it ; So, wait, what do I wear on a first date?

Each person and their individual style is different so here are just a few suggestions on what to wear on a first date based on the type of date. 

Meeting for Drinks / Dinner after work- Just because you’re meeting your date after work does not mean you have to show up in a stuffy suit. It’s easy to let your personality shine through a work outfit.  For example, pair a pencil skirt with a printed blouse and pumps (if they are comfortable) for a fun and modern look. Add the piece de resistance- a trench coat!

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A semi-casual / Non Formal dinner- In other words, not attire for dinner at The Plaza but for a lively restaurant downtown. Pair dark wash boot cut jeans with a sexy and sophisticated wrap blouse and 2 piece pumps. Add a clean clutch purse and a cool floral statement jacket for a trend right look. 

What to Wear on a Date

Sunday Brunch- Getting to know your date and noshing on some croissants and coffee sounds fabulous to me! On this date you want to look informal, yet put together. Pair boyfriend jeans, a relaxed floral top and pointy toe flats for a casual and updated look. Meeting on a chilly fall morning? Add a casual crop jacket. 

What to Wear on a Date

So there you have it, my take on how to dress for a first date. Now, I’d love to hear from you. Do you have a “winning” first date outfit? How do you choose your date outfits?


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Posted on September 8, 2014 .