Cheers, to your first date!
The first date is one of the most exciting parts of dating! Now that we’re adjusting to the post-pandemic life, the dating scene is also transitioning to IRL.
Ah, the pandemic life. Dressing up was either optional or “half” the effort that we usually needed! As we start meeting up for drinks and dinner dates, the struggle of figuring out what to wear on a first date for drinks is making its comeback.
The ideal date outfit is something that you feel comfortable in and boosts your confidence. There is nothing worse than wearing shoes that cause blisters or a distracting itchy sweater.
Let the outfit make a good first impression. Then, enjoy the date! Remember, the outfit is here to help, but YOU are the real star.
Remember, the outfit is here to help, but YOU are the real star.
The outfit will give you the confidence you’ll need for a successful first date. Once you have a good first date outfit formula down, dressing for future first dates will be a breeze–just rinse and repeat!
Keep reading for some outfit inspiration on what to wear on a first date for drinks and *maybe* pour yourself a glass of wine while you’re at it. Cheers! *glasses click*
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In This Post ➜
Keeping It Casual For A Date
Your date invited you out for casual drinks over dinner or maybe brunch. Now what? As simple as it may sound, casual dates are somewhat tricky.
The dread of being overdressed for a casual date is real. To avoid this situation, wear a casual dress. Short and mini dresses add a perfect feminine touch, while keeping the outfit casual perfect on a first date for drinks
A casual dress will make the occasion feel special and it’s literally the easiest outfit. Plus, it doesn’t look like you’re trying too hard. Effortless and chic.
Finally, slip on a pair of white canvas shoes to complete the relaxed date look.
Alternatively, keep it classic and simple with a cute top and jeans. Wear a pretty top with ruffles and balloon sleeves or an adorable peplum top to highlight the waist area.
Then, pair it with the classic high-waisted straight jeans for the ultimate casual look. Wear a pair of kitten heels to complete the ensemble.
FREE Year Round Capsule Wardrobe Checklist
Let’s face it, it’s hard to choose a stylish outfit everyday! This checklist is here to show you that you only need around 33 pieces to create easy and chic outfits all year long. Print it out or use it directly on your computer. Best of all, it’s FREE!
Dinner Date, But Make It Classy
Invited to a dinner and drinks date at a formal or fancy restaurant? Dressing up for a formal date may seem daunting, but it’s actually easier than you think.
Coordinating a full outfit with a top and pants can get messy. Instead, opt for a midi dress. The dress’ longer length is more elevated and formal appropriate.
Plus, midi dresses are very versatile and easy to dress up or down. Find one that makes you feel confident and comfortable. Then, make it your go-to outfit to wear on a first date for drinks whenever you meet-up at nicer places.
Wear a pair of block-heeled sandals for an extra boost in height, while keeping it fairly comfy with the block heel.
Another great alternative is a matching top and skirt set. Like dresses, matching sets immediately take the effort out of outfit coordination–it’s already done for you! Plus, they have the extra versatility of being worn as separates too.
Try a matching set that includes a crop top with a midi skirt. Bonus points if you can find a skirt with a side slit!
Also, put on a pair of neutral-colored strappy heels to elevate the look and add elegance.
Related: How To Look Expensive AF In 11 Tips & Tricks
Sunny Outdoor Or Picnic Date
Casual outdoor dates were pretty popular this past year. If you’re going on a picnic date, don’t forget to bring a picnic blanket, sandwiches, and a nice bottle of wine. 😉
Comfort is the key here when dressing for an outdoor or picnic date. Opt for long and flowy dresses for an easy outfit and extra comfort.
Try to avoid wearing restrictive or tight jeans, especially if you’re going on a picnic date. You don’t want to feel uncomfortable while sitting cross-legged on your date.
Maxi dresses are very comfortable and fit perfectly with the picnic aesthetic. Also, midi-length knit dresses are a good alternative. The knit material will hug your body’s curves, but it won’t be restrictive at all–perfect to wear on a first date for drinks.
In addition, wear espadrilles to complete the summery vibe.
Dresses not your style? Opt for a jumpsuit instead. They make dressing for a date a no-brainer since it’s an all-in-one outfit.
Jumpsuits are also extremely comfortable to move around in too. Go for jumpsuits that have a wide-leg silhouette for ultimate comfort, especially when you sit down cross-legged.
As for shoes, opt for a pair of block-heeled sandals to add some height and to avoid looking overwhelmed by the wide-leg silhouette.
What To Wear On A First Date For Drinks In Winter
Make sure you have a strong outerwear and layering game because winter is all about bundling up. Here are some easy-to-follow outfit formulas to help you look cute and stay cozy.
Wear an oversized sweater over a pair of high-waisted straight jeans. Make sure to tuck in the front part of the sweater to avoid looking overwhelmed by the baggy sweater silhouette.
Complete the look with a pair of ankle booties. You can never go wrong with a simple oversized sweater and jeans combo.
Going out for dinner and drinks? Elevate your look with a mini black dress, or LBD, and slip on a pair of thigh high boots. Finally, layer on a neutral-colored trench coat. This outfit is an attention-grabber and will leave an impression on your date.
What To Wear On A First Date For Drinks In Summer
It’s time for that summertime magic! Summer has the most outfit options for romantic date night drinks. Get ready for rooftop beer gardens, picnics, and beach dates galore!
For a casual look, go for a slimming off shoulder top and tuck it into a pair of skinny jeans. Wear a pair of ankle-strap heels to elevate the look or keep it comfy and casual with a pair of white sneakers.
Now you’re ready to stroll from the movies to a casual dinner to late night drinks.
Ready to dress it up for a fancy dinner and drinks? Wear a one-shoulder body-con dress with a pair of ankle strap heels. The one-shoulder cutout and the body-hugging fit is an ultra sultry combo that is bound to keep your date’s attention. 😉
What Should You Not Wear On A First Date?
The key to a successful first date outfit is to wear something that shows off your personal style and feels comfortable to you. Remember, your date wants to get to know YOU. Wear an outfit that gives you confidence on your first date over drinks.
That being said, there are a few tips I have for you to make sure you have a good first date outfit. Keep these tips in mind as you choose an outfit:
- Ditch Those Tall High-Heels – Really tall heels can be cute and super sexy, but not on a first date, especially if you’re not used to wearing them. You never know how much walking you’ll do. Let’s try to avoid limping and wincing in pain during the date. Plus, you don’t want any embarrassing accidents on the first date. If you’re too focused on walking in your heels, you won’t be able to focus on being yourself either.
- Stay Away From Too Revealing Clothing – Showing some skin is sexy, but showing too much can be provocative and give off the wrong vibe. I’m talking about the skimpy tops that show way too much cleavage or mini-dresses that leave your butt cheeks hanging out. This is especially important if you don’t feel comfortable revealing too much skin. Don’t feel pressured to show off skin if you don’t want to. In fact, some modesty can leave your date wanting more.
- Leave The Messy & Unflattering Clothes At Home – If your clothes have holes, look very worn-in, or are extremely wrinkled, leave them at home. Likewise, any clothes that are ill-fitting and not deliberately styled will make a bad first impression.
- Makeup Should Be Low Maintenance – Don’t beat your face with layers upon layers of makeup. Remember, less is more when it comes to makeup. Use some concealer to cover up a few problem areas and wear a simple MLBB lipstick, or a shade that resembles your natural lip color. Don’t wear so much makeup to the point that it obscures who you are. Plus, your date will probably notice it too.
- Skip Clothing That Makes You Uncomfortable – Wear clothes that make you feel comfortable. There is no need to go overboard just to impress your date. If a t-shirt and jeans makes you feel happy, then wear it. Your date wants to go out with you because they like you for a reason, so don’t overthink it.
FAQs & Tips To Dress Appropriately For Dates Over Drinks
Can You Wear Jeans To A Bar Date?
Yes, in fact, jeans are a bar-going classic. Wear a pair of dark straight-leg jeans for an easy polished and casual look.
Yes, in fact, jeans are a bar-going classic.
Try to avoid jeans with a lot of distressed detailing or cuts and slouchy silhouettes. One or two cuts would be fine, but too many cuts and a baggy silhouette will look sloppy.
However, if you are heading to an upscale bar, check the dress code first. Some bars may have stricter rules against jeans and t-shirts.
Can You Wear Leggings On A First date?
Leggings are actually incredibly versatile as they are super comfortable. The real question here is–are leggings appropropriate for first dates over drinks? I’m delighted to say that they are!
It all comes down to what you pair with your leggings and the type of leggings. If you want your leggings to look polished, pair them with some pointed heels and a cute blouse.
Avoid wearing leggings with mesh detailing, color-blocking, or prints. Opt for simple leggings in one color, such as all black. Also, faux-leather leggings look very polished and add a bit of an edge to an outfit.
Can I Wear Flip Flops To A Bar?
Flip flops are comfy and easy to wear, but they lack a lot of versatility! I wouldn’t recommend wearing flip flops at all on a date to the bar.
I don’t mind wearing flip flops to the pool or the beach, but not to a bar.
I don’t mind wearing flip flops to the pool or the beach, but not to a bar. In fact, some bars have strict rules against flip flops, so just avoid them altogether.
Instead, wear a pair of heeled sandals. They offer similar comfort and you won’t have to worry about getting stepped on!
Final Thoughts
First dates are stressful, but one way to reduce the stress is to wear an outfit that is 100% comfortable to YOU. Remember, your date wants to know more about you, so don’t let the outfit overwhelm who you are.
A good outfit will make an impression, but your personality will be the most attractive aspect that will hopefully ignite that spark. 🥰
FREE Year Round Capsule Wardrobe Checklist
Let’s face it, it’s hard to choose a stylish outfit everyday! This checklist is here to show you that you only need around 33 pieces to create easy and chic outfits all year long. Print it out or use it directly on your computer. Best of all, it’s FREE!
Disclosure: This post may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you. Please read my disclaimer for more info.
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