You’re going on a first date and you’re stressing out about what to wear on a first date for drinks. While we can’t give the exact answer, we can give you some general advice to keep in mind, a few outfit ideas, and ways to make the outfits feel more like you.
The important thing is that you have fun and learn about your date while feeling completely comfortable in your skin and authentic to you.
This post is all about what to wear on a first date with drinks.
Reminders Before You Get Started
1. Wear what you’re comfortable in and stay in your comfort zone
First dates are scary enough without feeling uncomfortable in your own clothes. You deserve to wear something that feels good on your body. Comfort goes beyond the way it feels on your body. It also encompasses the way you feel when you look in the mirror.
Even the most well-fitting, so-called “perfect first date outfit” can make us feel like our body insecurities are at an all-time high. That’s perfectly understandable since learning to love your body is a lifelong process that fights every message society sends you every day.
So, choose an outfit that makes you feel comfortable. While you may have your date at the top of your mind while you’re getting dressed, you have to show who you really are. Maybe this date won’t go any further than a fun night with someone you never plan to see again.
Still, you deserve to be your authentic self and show that self through the clothes you wear. The best way to have a good time on your date is by wearing what makes you feel good inside and out.
2. Focus more on looking for green flags than making a good first impression
Focus on your date. The last thing you want to do is focus so much on impressing your date that you forget to ask yourself if they impressed you. It’s normal to be overwhelmed and intimidated by first dates, especially if the other person is so attractive they make you nervous.
Even then, you’ve got this. Take a breath and remember that this first date is just as much about impressing them as it is about asking yourself if you’re impressed. Let those first date nerves to make a good impression fall the side of the conversation. Get curious about your date.
Identify both the red flags and the green flags as they pop. Remember that the most important thing about this date is learning about the other person and enjoying yourself whether a second date is in the cards or not.
3. Ask for opinions from your best friends
When in doubt, always send a quick picture to your friends. Make sure you find people who you trust and who have your best interests at heart. Plus, choose people who respond quickly because (hello!) you’re in a rush and stressed on the way to your cute date.
Forget all of the outfit formulas and videos you see on social media about how to put the best outfit together. Now is the time to rely on the people in your life who can be honest without being brutal. Ask them if the shoes match the shirt or dress.
Avoid asking questions like “Do I wear a pair of heels to a drinks date?” or “Why aren’t we going on a dinner date?” You want opinions from your friends, but you want the types of opinions that won’t confuse you or make you feel conflicts.
The odds are that you will get multiple, confusing, unhelpful answers if you ask your friends a simple question like “How do you define the perfect look for a casual date?” They will answer in different ways and unintentionally make you second-guess yourself.
So, keep your questions simple and easy to answer. At the end of the date, you can leave your house knowing that you are looking like the best version of yourself even if you take none of the advice your friends gave you.
4. Remember that the perfect outfit doesn’t exist
Perfection is futile, as they say. But, seriously, avoid looking for the perfect outfit. That’s why we started this blog off by telling you to wear what feels good. Cute first date outfits look different to everyone.
Plus, the more you cater to what you think you should wear and less about what makes you feel cute or good, the more likely you are to feel uncomfortable in your own skin and let that show to your date.
Maybe this is your first time meeting someone new and maybe that’s scary. On the other hand, maybe it’s exciting, fun, and just a little bit casual. So, when you craft the outfit you’re going to wear for happy hour, remember that your date is a person in real life just like you.
There’s no such thing as sending them the “wrong message” with your outfit and scaring them off because you chose the wrong pair of jeans or casual dress.
The only “faux pas” you can make is wearing something that is designed to impress your date without impressing you because, at the end of the day, your opinion is the only one that matters enough to affect what you wear and define as a “good look.”
5. Consider the time of day of the date
Yes, we did just say there’s no “perfect outfit,” and there isn’t. But, there are outfits that are more likely to protect you from frostbite or heat stroke and there are ones that are less likely to. In other words, wear something weather and time-appropriate.
If it’s a cute coffee date in the middle of the day when the sun is out, wear light material with fewer layers so that you can breathe.
If it’s not a daytime date and it’s snowing, then you may want to forgo the midi dress and dress shoes in favor of an extra layer and something more insulating and weather-resistant. Overall, remember to take the weather into account as you prepare for your date.
6. Involve your personal style in the outfit no matter what fashion trends say
Ignore any fashion trend that tells you to wear something you don’t want to wear. Maybe this is an unpopular opinion because times change and so does style. However, if you like the style of clothing you wear and social media calls it “outdated,” it’s a good idea to ignore that.
Fashion trends will constantly change, but what won’t change is the constant societal pressure to change with the trends and fit your body into a certain skinny, light-skinned, westernized standard of physical beauty that just about no one can achieve.
The people who seemingly fit that standard are still told they’re not enough. So, let’s not listen to that and remember that your best self wears what you love to wear. Nothing more and nothing less.
WHAT TO WEAR ON A FIRST
DATE WITH DRINKS:
Date Night Outfit Ideas to Inspire You
Now that we’ve addressed some general advice when deciding what to wear on a first date for drinks, we want to offer some casual first date outfit ideas. These outfits are fully customizable and are designed to come with options that dress them up and down with layering.
Remember that any fashion advice we give you is completely based on personal experience and personal style. What matters most is that you feel special, cute, and excited to go on your first date regardless of how much of these suggestions help you get there.
1. A little black dress with a leather jacket and high heels
If you’re going for a drink date, then it’s worth mentioning that dressing down your outfit may make you feel more comfortable. Whether you end up at a sports bar or fancy, champagne bar, you can rely on layers to help your outfit adapt.
A leather jacket or sports coat is the perfect way to accessorize your dress without taking away from its cuteness. Plus, the high heels will go perfectly with any dress that shoes too much of your leg for flats to match.
Forget everything you’ve heard about leather jackets being too cool for you (and we do pleather, here, since we’re animal lovers, or opt for a thrifted leather option!). This is the time to put one on and watch as it elevates your already incredible outfit.
It’s amazing how the perfect little black dress instantly feels slick and badass with a leather jacket attached. The right set of heels will make this outfit over the top and set you up for the best date.
2. A white shirt with skinny jeans and white sneakers
There’s nothing better than a simple outfit like a good old T-shirt (or blouse) and skinny jeans with sneakers. Not only is it versatile and can change with the scenery, especially if you opt for skinny jeans that don’t have holes in them, but it’s mostly comfortable.
Sure, skinny jeans may squeeze your legs in relatively uncomfortable ways (it’s okay to size up!). But, the sneakers will make it easy for you to maneuver on the dance floor, between bars, and manage in standing-area-only types of joints.
You can choose how to customize this outfit to fit your personality the best. Maybe you want to add some chunky gold jewelry, a minimalist necklace, or some bangles to tie everything together.
Or maybe you’re more of an off-the-shoulder t-shirt kind of person. Whatever it may be, this has the potential to win any bar date regardless of whether you end up in a dive bar or fancy club.
3. A crop top with high waisted jeans
Since high-waisted pants are some of the best things to ever be invented, they have to make the list for date ideas. The comfy crop top with a comfy pair of high-waisted jeans shows off your hips without showing off your stomach, if that makes you nervous.
Plus, your crop top combined with a pair of high-waisted jeans will give some cute angles without the effort of wondering if your jeans allow for room to bloat. You get all of the comfort and all of the cuteness. How you finish this outfit off is your choice.
Personally, at Knockoff Therapy, we love to create some continuity between the shirt and pants with an oversized coat or blazer and some cute jewelry. Add some ankle boots or flats for a great option to take with you on your first date for some casual drinks.
4. A midi dress with a denim jacket and sandals
Midi dresses are an oldie but a goodie. You get comfort and airflow and soft fabric with the cuteness of a dress. Plus, they have some built-in lines.
So, you can wear something that accentuates the parts of your body you may want to show off while giving you some space in the areas that might make you feel more insecure. Regardless, midi dresses are such a good choice since they come in so many different shapes and sizes.
They’ll all hit your calves, but the rest is up to you. You can choose the neckline and waistline that fits your body type best. Add a neutral belt to your waistline for some more accentuated form if you feel like the dress is swallowing you up rather than doing you any favors.
Include a jean jacket for a change of scenery within your outfit and some basic warmth if that is necessary.
Sandals are the perfect addition because they’ll add interest to your outfit, can be very comfortable to walk in, and maintain the theme of airflow within your outfit (perfect for an evening date in the summer!).
Personalize Your Outfit to Fit You
We’ve gone over a few outfit ideas, but it can be hard to make them feel like you. The suggestions below can spark some creative ideas on how to make each outfit represent the real you.
Even if the suggestions below don’t apply to you, think about ways that you can use these ideas with the accessories you already have to create an outfit that feels good to you.
1. Add a pair of statement earrings
The right set of earrings can be the focal point for an entire outfit. Rather than drawing attention to your dressy top, you can have people focus on the pieces of art that you’ve attached to your ears. We can’t sleep on the effect that accessories have on outfits.
We can take a relatively plain, monochrome outfit and make it more interesting with bright colors on our earrings or larger earrings. Bonus points if there’s a story behind the earrings that opens up space for conversation on your date.
Plus, you can make an outfit that you wear every day and change into something almost unrecognizable by pairing it with the right statement earrings. This is the part where you bring your personality into it. So, if statement earrings speak to you, then let the creative ideas flow.
2. Consider some flip flops
Flip flops can be a bold choice, especially if they’re more on the casual side and made of foam rather than sleek and more formal. Still, flip flops will make it clear that you know who you are, and flip flops are a part of that.
They can be a bit harder to style unless you have a brown or black pair that stands out a bit. The good news is that no first date has a dress code because you’re still learning about each other.
If flip flops feel authentic to you, they will serve as a great way for your date to learn more about you. It’s unlikely that your date won’t notice them. Whether they react to your flip-flops or not may help you learn about them in turn.
So, yes, the choice to wear flip-flops does not have to be complicated or contain subtext. But, if we’re honest, it does say something about who you are and it can help you communicate to your date more about you.
3. Bring a nice watch along with you
Just like a statement pair of earrings can change a whole outfit, a nice watch can alter the way people see your outfit. A nice watch is best paired with a three-quarter length sleeve that is either rolled up or naturally that length.
This length will draw attention to the watch and add interest to your outfit. Bonus points if you layer your outfit with an oversized blazer or coat that is also rolled up to make your outfit slightly more formal while also drawing even more attention to your watch.
If you choose to wear a watch, we recommend that you let it show the entire time you’re wearing it. This is less to “brag” about your wealth or the fact that you own a nice watch. Instead, it’s more to lean into the style of the watch and make use of wearing it.
Plus, you can actually use it if you can always see it. Be careful not to use the watch as a tool to accidentally make your date nervous or think you’re uninterested by checking it frequently.
