What to Wear on a First Date
Dating is hard. Once you go through the process of securing a date you’re actually excited about— the real stress begins. What will we talk about? Will we have instant chemistry? What if it gets awkward? Will I like him (and flirt with him)? And the most serious question of all:
WHAT WILL I WEAR?!
When I initially started over in the dating world, I’d choose what to wear on a first date just like I’d choose any outfit of the day: I’d try on several options and decide what to wear based on how I felt.
As a woman, it’s common for the way I feel in an outfit to change day by day (especially after telling myself last night I “deserved” cookie dough… I’m sure you can relate).
Then there’s color: sometimes I’m in a “teal” mood while some days black and grey are calling my name.
Don’t even get me started on accessories! There are many times I base my entire look around a statement necklace I’m dying to wear.
Before a first date, I can’t tell you how many times I found myself running around the room, trying on multiple shirts, changing my jeans, realizing the black bra under the yellow shirt isn’t going to work, and standing in front of the mirror wearing two different shoes. My room would literally look like a tornado had hit it.
The Importance of What You Wear
Choosing an outfit for a first date is far more stressful than deciding what to wear for a girls’ night out. There are several factors to consider when selecting an outfit for a first date.
Your outfit is the ultimate advertisement and initial impression when first meeting a date.
I will show you how to instantly and forever take the stress away associated with choosing an outfit for a first date.
What to Wear on a First Date
Once you say “yes” to that date, here are a few details you need to consider:
Location, Location, Location
The first detail you’ll want to establish is: Where are you going?
Are you meeting for happy hour on a Tuesday? Will you be going to a nice dinner Friday night? Are you meeting for a cup of coffee on a Saturday afternoon?
Next, you need to determine if it’s more casual or upscale. About 80% of my first dates were at the same location! (Yep- you read that right!)
I met the majority of my first dates at a cute little wine bar close to my house. Suggesting this location insured I was in a familiar area and that I always knew what to expect. (Plus, a glass of wine is a great low-key first date.)
Occasionally, a first date would insist we meet for a fancy dinner. If I had never been to the restaurant, I always researched the atmosphere. Dressing appropriate for the specific location is key to feeling confident and beautiful.
Girl Next Door
We’ve all heard about men being attracted to the “girl next door” look. Most men are attracted to a women that leads with her natural beauty— not her blue eyeliner.
I love playing in makeup and trying new looks. However, a first date isn’t the time to try something new with your eyeshadow from Pinterest. If you show up with too much conturing, thickly painted on eyebrows, and overdrawn lips— men can quickly label you as “high maintenance”.
Now, I’m completely aware that sometimes applying makeup in a “natural” way can take just as much time and eyeshadow as trying a new smoky eye. It’s not necessarily about the amount of make up as it is about the appearance of your makeup.
I’m not suggesting you be somebody you’re not, but I am suggesting that you lead with your more natural self.
You want to be the best version of yourself.
Newsflash: Men don’t follow trends.
Last winter, Kevin and I were getting ready for a Christmas party. I walked out feeling all pretty in a new Anthropology peplum top and skinny jeans. I could tell by the look on Kevin’s face that he was trying to process what the heck I was wearing. I decided to just ask him, “How do I look?”
He had a perplexed look on his face as he cautiously answered, “I don’t like these ruffle thingys.”
We’re a little past the first date, so of course, I still wore the top out (and felt fabulous). The women at the party complimented me while the men probably also wondered what those “ruffle things” were. While I adore this peplum top… I would never allow one of my friends borrow it for a first date.
It’s perfectly ok to love trying trends and creating new looks… but not on the first date. If you dress too trendy, you run the risk of your date not understanding what your’re doing.
In fact, your trendy outfit could become distracting to your date and take away from your opportunity to get to know each other.
Once again: I’m not trying to change you. Consider this:
Would you naturally wear a suit everyday? Probably not. Would you choose to wear a suit to an interview? Absolutely. Why? Because you only get one first impression.
Does altering what you’d choose to wear for a job interview vs. the clothes you’d naturally pick out most days in anyway alter who you actually are? Absolutely not.
I’d never suggest you to be someone you’re not.
I just don’t want anything to get in the way of the real you shining through or prevent you from the opportunity of getting to know your date.
I love a bold statement necklace. The colors, the size, and the design can really bring an outfit together.
However, “Girl Pretty” is a real thing.
Just like with trends, men don’t really “get” the whole crazy accessories us women do.
I can literally spend hours shopping in Charming Charlie (a trendy jewelry store). Many times those new purchases dictate what I’m going to be wearing the following week.
Too bold of accessories can easily distract a man’s attention from your conversation.
I’m not saying to not wear big earrings if you like big earrings (in fact, I wore big earrings on almost every one of my first dates because that’s a big part of my style ), I’m just saying to not go overboard.
Pick one bold accessory. Don’t pick ten.
I want your shinning personality to captivate the room… not your sequined scarf with your sequined headband and your sparkly bib necklace.
(While I wouldn’t suggest you wear an over the top accessory on an actual first date, I’d tell you to “go for it” when you’re aiming to meet new single men. Instead of being a distraction, it becomes a conversation starter, making you more approachable.)
My Little Secret
So what’s the secret to eliminating all stress with it comes to what to wear on a first date?
Yep— wear (almost!) the same outfit on every first date.
I’m being serious here! Go through your closet, try on all your clothes, and pick out your perfect “First Date Outfit”. It’s nice to have two: one casual and one more dressy.
My casual first date outfit:
My favorite skinny jeans and a simple white shirt. If it was cold outside, I paired it with a warm sweater and boots. If it was warm outside, I brought a cardigan and wore sandals. My accessories would change with my mood.
My dressy first date outfit:
A grey and white shift dress paired with black heels.
Once I had settled on a “first date” outfit, all the stress instantly dissipated associated with getting ready for a a date.
Now, were there dates that I didn’t wear this exact outfit? Yes, of course!
I wore a sundresses for brunch dates and heels when I was in the mood. But for the most part, the stressful, “WHAT WILL I WEAR?” panic didn’t overcome the excitement when getting ready for a first date.
Don’t let that frenzy in your closet take place again. Sift through your wardrobe and decide which 2 or 3 outfits make you look (and feel!) your best. If you feel like wearing something else that night… then wear it. Just know, you already have a basic but stylish outfit you know you look awesome in.
When you feel confident in your outfit, it allows your true beauty to shine through.
No one has to know you virtually wear the same outfit on every first date… unless you go to the same wine bar. In that case, just sit in different sections so you get different waitstaff 😉