What to Wear on the First Date:

It’s your first date, and you’re excited! But what should you wear? You want to look cute and be comfortable, but you also don’t want to be too dressed up or underdressed. Don’t worry—we’ve got your back. Here are some tips for dressing for your first date:

  1. Dress comfy. If you’re going out with someone that you really like, chances are they’ll want to hang out and get to know each other. Make sure that whatever outfit you choose is comfortable enough for a long night of casual conversation.
  2. Don’t overdo it on the makeup. If your date is getting ready for work in the morning, they’ll probably appreciate it if you leave their eyes alone (or at least do light eyeliner).
  3. Keep it simple and classic; avoid logos and anything too trendy or flashy—you don’t want this person thinking “Oh no, I’m dating an Urban Outfitters model” later on down the road!

What to wear on the first date

You’ve been waiting for this moment. You’ve been dreaming of it. You’ve been planning it since the moment you knew it was possible. And now it’s finally here: your first date with [name of your crush].

You want to look good, but not too good. You want to be yourself, but also show off your best self. You want to be comfortable and confident, but also show off those killer shoes (or those adorable socks).

We’re here to help! Here are some tips on what to wear on your first date:

It’s the first date, and you’re going to be meeting up with someone you haven’t seen in a while. You want to look good, but not too good—you don’t want to come across as trying too hard or desperate. You also don’t want to look like a slob or like you’ve just rolled out of bed after staying up all night binge-watching your favorite Netflix series. So what do you wear?

Well, let us help! We’re going to give you some options for outfits that will make sure your first date goes well and leave a good impression on your potential new partner.

You’ve got a date with your crush. You’re going to meet at a new café, and you want to make a good first impression. But what should you wear?

You want to look cute, but not too cute. You don’t want to come across as dressed-up for a special occasion, but you also don’t want to look like you just rolled out of bed and put on whatever was closest to your face.

So what do you wear?

The key is to look approachable—and that means being comfortable! So don’t worry about perfection, just get dressed however makes you feel confident and put-together in your own skin.

If you’re going on a first date, you want to look your best. But how do you find that perfect combination of casual and classy? Which shoes go with which outfit? And what the heck should you do with your hair?!

With this guide, we’ll walk you through everything from choosing your outfit to planning the night out. We’ll tell you what to wear for different types of dates, whether it’s a casual coffee date or an elegant dinner. We’ll even tell you what to do if things don’t go as planned!

For a first date rule, avoid extremes like heavy makeup, overly trendy outfits, or showing too much skin. Natural and minimal is always best for the first date. Wear something that looks good on you, neither too tight nor too loose, just something that compliments your figure.

STYLE
5 TIPS FOR CHOOSING A FIRST DATE OUTFIT
By AKINWALE AKINYOADE
31 January 2021 | 1:00 pm

5 Tips For Choosing A First Date Outfit

Admittedly, dressing up for a first date can be nerve-racking considering you want to impress without looking like you are trying too hard.

So you are meeting that guy your friend introduced you to, or maybe it is the cute guy from the dating app you have been texting with.

Give yourself the boost of confidence you need for the first meet-up with a majorly hot outfit that will make you feel like a super babe.

Comfort Is Key
You don’t want to be caught fidgeting throughout your date. Keep your comfort in mind when picking out first date outfits. Don’t wear anything that you can’t walk in, eat-in, or breathe in! Comfort is key no matter what.

Choose Your Best Colours
It is best to dress in colours that you are often complimented on. Not only will you be comfortable, but you also don’t have to worry about whether you chose the right outfit.

Let The Location Be Your Guide
Always check out the location of where you have agreed to meet so that your outfit reflects the environment. You don’t want to be too warm in an environment that would have required you are light with your outfit.

Avoid Extremes
For a first date rule, avoid extremes like heavy makeup, overly trendy outfits, or showing too much skin. Natural and minimal is always best for the first date. Wear something that looks good on you, neither too tight nor too loose, just something that compliments your figure. For makeup, enhance your feature but don’t overwhelm it.

Be Your Best Self
Wear something that truly makes you feel like the best version of yourself. Because when you do that, you will have more confidence. And the more confidence you have, the more you will smile, the more you will engage and chances are, the more dates you’ll have!

What to Wear on a First Date? We Asked the Experts!
written by MADELINE GALASSI
SEPTEMBER 13, 2021
The Everygirl’s product selections are curated by the editorial team. If you buy something through our links, we may earn an affiliate commission, at no cost to you. We only recommend products we genuinely love.

Source: Jules Kennedy for The Everygirl
No matter how you cut it, first dates are usually preceded by a lot of nerves, at least a little bit of panic, and handful of jitters sprinkled on top. The stress sets in, and before you head out the door, you second-guess absolutely everything—including the outfit you picked out after frantically googling “what to wear on a first date” all day.

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Listen up: when you’re dealing with first-date nerves, the last thing on your list of stressors should be your outfit. First dates aren’t the time to reinvent the wheel when it comes to what you’re wearing; it should be something you know you’re comfortable in, and we’re here to help figure out exactly what that is.

Whether you’re heading out on a daytime coffee date or have reservations at the cool, trendy new restaurant in town, stop typing out a frantic text to your group chat, and leave the outfit planning to us.

Do’s and don’ts

Do

Wear something you’ve already worn and know you’re comfortable in
Break out your pieces you usually reserve for special occasions
Think about what makes you feel the most confident
Don’t

Wear a brand-new piece that risks being uncomfortable, like needing to mess with a falling strap or digging-in waistline
Try to dress in a way where you won’t feel like yourself
Overthink it

Daytime Coffee Date

A daytime date poses a little bit more of a question mark than something like a dinner or drinks date might, but it should be approached as being that much simpler.

This is all about elevated basics. A cute pair of jeans, tank, and sneakers exudes just the right amount of effortless while also being ultra-flattering. If you run cold, make sure you bring a layer to throw on top, so you aren’t worried about your temperature more than hitting it off with your date.

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GOOD AMERICAN
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NIKE
Air Force 1 Shadow Sneaker
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QUAY
Oversized Square Sunglasses
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Casual Dinner Date

In our experience, a casual date’s vibe can be more difficult to strike than one that veers more on the fancy side for one reason: the fear of feeling overdressed.

To keep it as simple as possible, opting for a casual dress is the easiest and best bet. You’ll feel date-ready and like the event is a little special, but won’t look like you tried too hard. The best part? It’s a one-and-done look, so your pre-date stress will be kept to a minimum.

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Long-Sleeve Smocked Mini Dress
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H&M
Linen-Blend Crossed Back Dress
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BP.
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ELOQUII
Cuff Sleeve Romper
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H&M
Ribbed Jersey Dress
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SEYCHELLES
Cross Slide Sandal
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MANGO
Leather Strap Sandals
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Post-Work Drinks Date

A post-office drinks date is, in our humble opinion, one of the best types of dates you can have. It automatically feels like less pressure because you’re already out and about, and if you’re anything like us, have talked about every possible thing that could happen during the date with your coworkers all day.

Since you’re coming straight from the office, arriving in a look that’s office-appropriate is expected. We’re partial to a tee, blazer, jeans, and a pair of sneakers to hit the nail on the head of “working woman heads on date.” If you want to make it a little sexier, opt for a more form-fitting tank rather than a tee under your blazer.

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VEJA
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JW PEI
Mini Croc Flap Bag
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Elevated Dinner Date

The most classic of dates: a nice dinner out. Rather than messing with figuring out a pants and top to wear, a dress is the best bet.

To make it a little more elevated, a midi-length dress is a great option for a nice restaurant. It’s easy to make work for a wide variety of locations and finding one you’re comfortable in is a great go-to to turn to whenever the nice-date jitters turn up.

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BP.
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MANGO
Baguette Shoulder Bag
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Picnic or Outdoor Date

After 2020, the rise of the casual, outdoor date is here, and it’s a whole new variety of date to have to navigate the outfit waters of. To combat the questions, we’re taking the nap dress trend and running with it.

When you might be sitting cross-legged on the ground, you don’t want to mess with tight jeans or a risk of feeling uncomfortable the entire time. A long, casual dress not only screams picnic, but will make sure you can sit and maneuver any way you like all night long.

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ELOQUII
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H&M
Rib-Knit Dress
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H&M+
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ELOQUII
Tie Front Maxi Dress
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H&M
Floral Maxi Dress
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Twist Strap Flip Flop
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MALI + LILI
Woven Straw Tote
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What to wear on first date for guys

A collared shirt is almost always a must for a first date. Unless the two of you are off on a serious sporting adventure, wear a button-up shirt or polo. For a cozy dinner, choose a button-up shirt in a classic print, like windowpane or gingham.

Any tips for what to wear on a casual first date? I want to look sharp, but, y’know, not like I’m trying too hard. Damon
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The hardest part is over. You asked out your crush, your crush said yes. Keep the momentum going in a first-date look that exudes casual confidence. If you’ve got a laid-back style, the easiest way to take that look to date night is to step it up. More buttoned-up in your day-to-day? Keep your look polished with dressed-down options in tailored cuts.

Here’s how to dress for a casual date.

Stitch Fix men’s outfit laydown featuring blue denim, grey t-shirt, plaid flannel button-up, navy puffer jacket and brown chukkas.

DO DARK DENIM
A casual date calls for denim. If you told your date casual, they will most likely be in jeans or a casual dress, so it’s important you stick to the dress code (translation: do not wear a suit). Instead of your relaxed fit or light-wash weekend denim, opt for a dark-wash straight-leg jean. It’s universally flattering and will work with a variety of shirts—plus, the darker wash will lengthen your legs, making you appear taller. Be sure to add a leather belt to your jeans if your shirt will be tucked.

Stitch Fix Men’s grey wool peacoat, red and blue plaid flannel shirt and brown slim-fit jeans hanging on a rack with grey chukkas on a white podium.

LAYER WITH STYLE AND PURPOSE IN MIND
Use the cooler fall weather to add depth to your date night look with a layering piece. A sporty but elevated bomber jacket, a casual ¼ zip sweater or a classic sport coat gives you a polished, dimensional look without too much fuss.

Stitch Fix Men’s outfit laydown featuring multi-colored button-up shirt, brown colored skinny jeans and grey oxford shoes.

DATES CALL FOR A COLLAR
A collared shirt is almost always a must for a first date. Unless the two of you are off on a serious sporting adventure, wear a button-up shirt or polo. For a cozy dinner, choose a button-up shirt in a classic print, like windowpane or gingham. Headed to an outdoor concert or a leisurely dinner al fresco? Try a conversational print with a touch of seasonality.

OPT FOR SHARPER SHOES
When in doubt, a dressier shoe is the best option. While oxfords are best saved for suits and suit separates, a Chelsea boot or a derby shoe, for example, will work with dark-wash denim or chinos (if you insist). A canvas sneaker is acceptable for a more laid-back date, but don’t pull out your old, tattered sneakers. A clean, like-new shoe shows you care and took time to prepare for the date.

KEEP ACCESSORIES TO A MINIMUM
Keep your jewelry to a minimum on first dates; stick to a classic watch or cuff. Simple is better when it comes to first impressions. Their focus should be on you, not your necklace or class ring.

PRESENT YOUR BEST SELF
Finally, here are a few first date dos (though we know you’ve got this):
Be prompt. Picking them up at 7? Be there at 7. If you’re meeting somewhere, get there 5 minutes early so she will see you when she arrives.
Have questions ready. This shows you’re interested in getting to know them. Don’t ask them all at once. Let the conversation evolve.
Put your cell phone away. Keep it out of sight to eliminate the temptation to check it. If you must have your cell phone out, set it face down on the table.
Have a plan. Don’t pick them up and say “what should we do?” Choose your destination beforehand—then have a couple options ready for later in the evening if all is going well (like after-dinner drinks at a jazz bar or ice cream and a walk).
Above all else, be yourself. Ready to have those go-to date night looks in your wardrobe? Take your style quiz, schedule a Fix and have five curated pieces arrive right to your doorstep. Give everything a try in the comfort of your own home. Keep what you like and send back the rest. Shipping and returns are always free, it’s that simple.

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