When the pressure is on, most girls usually go or the safest trick in the book: the little black dress. Ever since its creation in the 1920s, the little black dress has been donned by women across the globe in hopes of looking seductive and sultry on a big first date. It’s somehow established itself as a classic, universally flattering style for all women to wear throughout the decades.
But now, the times have changed and so has our taste in first date attire. First dates have gradually become more and more casual, with simple dinner drinks being the ideal choice over a fancy 5-star restaurant. So, our style is calling for something a little more casual, which is why we’re tucking away our LBDs and slipping into something more comfortable. No, that doesn’t mean something more revealing, that means grabbing some leggings, a loose-fit blouse, or anything that will make us feel calm and cool during our dates.
Staying casual for the first date doesn’t mean you have to look undone or lazy. Dressing for a date is kind of like getting ready for a job interview: you want to look composed, but not overdone. A small heel and something you’d wear on any casual night out will do just the trick to nail your date night looks. Let’s put it this way, if they’re truly Mr. or Miss. Right, then they’ll think you look amazing no matter what you wear (to an extent). That’s the cheesy, yet honest, truth about dating.
But, we’re not here for dating advice, we’re here for style guidance. Which is why we’re serving you some of the hottest casual first date looks that we’re ready to wear on our next major summer date night. These looks are fun, fearless, and playful, which is the perfect mix for turning a nervous date into a night of a lifetime. When you think about, dressing down for a date totally makes sense. You’ll feel calmer, more true to yourself and your style, and just lightly glamming up will still give you a sexy confidence that will draw the attention of any date.
So, take the shorter route with your date style by trying on some of these top date picks. No little black dresses here, just laidback and tranquil outfits that can be worn at your date’s favorite dive, or even to the upscale bar that everyone’s been talking about. Wherever your date may take place, these calm stylings will surely make your style shine without making you look high maintenance.
In need of a new date night outfit? Then ditch the LBD for these casual first date looks.
The bad weather look
We’ve all been there—the weather has gone sour but you’ve got a date scheduled and you just don’t want to cancel it. We’re getting to the point in the fall season where bad weather days happen at least once a week; they’re almost unavoidable. Even though you can’t bear the thought of stepping outside, this is an evening you’ve been waiting for. And you know that the only thing worse than braving the cold would be a night spent on your couch thinking about what you might have missed out on. Your best course of action on an evening like this one would be to dress accordingly. Plan your outfit as strategically as you can, so you can be sure that you’ll feel warm and comfortable no matter what the weather throws your way. And you have to pick a look stylish enough for a casual date night, of course.
We recommend you opt for a pair of scuba leggings because they are both warm and comfortable. If you find a sturdy pair with a button fly closure, it basically looks like you’re wearing a trendy pair of jeans. Pair that with a crewneck, loose-fitting sweater to add to the cozy yet sartorial look, but be careful not to pick a style done in cashmere or wool in case it rains. And then to be completely weather-ready, find a pair of rainboots in a Chelsea style.
The jeans and a t-shirt look
If your definition of casual means all-out casual, it’s safe to assume that jeans are your weapon of choice for a first date look. Jeans are actually the safest bet for most of us on a first date, because we all have that one (or more) reliable pair that we know we always look good in, and most importantly, feel confident in. Jeans and a t-shirt might sound a bit too laidback for a first date night outfit, but if you select your pieces well, a pair of jeans can be exactly what you need to get your look perfect.
We recommend a flowy t-shirt with an intricate or naturalistic pattern, preferably in a neutral palette. Of course the jeans should be whichever pair you like best, but keep in mind that a dark pair of skinny jeans can go a long way when worn with a simple t-shirt. And then finish the look in a pair of black booties, perfect for fall. Maybe opt for a heeled style.
The comfortable shoes look
A first date can take you anywhere, especially in fall time. A date might start out as casual dinner drinks, and then turn into an evening stroll, trip to a seasonal haunted house or something really cute like mini golf. And the last thing you’re going to want to worry about during a first date is aching feet. So if you’re interested at all in the idea of dressing from the bottom-up, meaning you’ll pick your shoes out first, be sure to pick a pair that is as comfortable as it is cute. Because yes, comfort is key, but you’re still on a first date.
Birkenstocks are always a good choice when it comes to comfortable footwear. And, with most styles of Birkenstock, style comes along for the ride too, especially as mules are becomingly increasingly coveted. In the fall time, a good mule with a tall knit sock can go a long way to defining an outfit. Just pick a simple dress, maybe with a flowy form, and let the shoes do the walking and the talking.
The “I don’t care if it’s casual, I want to dress up a bit” look
While the majority of the population agrees that a trusty pair of jeans is always the way to go, there are some of us who just tend to feel more comfortable in a dress. And first date dressing is ALL about feeling comfortable and feeling like yourself. While being underdressed is often what we worry about most in getting ready, with a casual date, you definitely don’t want to feel overdressed. That being said, you can make a dress work in a look without it being too much for the occasion.
We suggest a sweater or sweatshirt dress, teamed with a simple bag and a slightly heeled pair of mules to play up the look a bit without going to an extreme.
The on-trend look
For those of us who are really into this season’s trends, there is a clever way to make certain aspects of a trend work for a casual date without being over-the-top.
We love an oversized plaid blazer with a simple denim shift dress to play two trends off each other. Then add a tall pair of over-the-knee boots to make sure you’re weather-appropriate for fall.
The mini skirt look
Similarly to the dress look, you can make a mini skirt work for a casual first date without being too dressed up. Our suggestion? Neutrals. For casual outfits in fall, always go neutral.
For your mini skirt first date option, pick an oversized, cozy knit sweater and pair that over a color-matched skirt and flats combo. Remember, when dressing casually, you should opt for flats over heels, especially when there is a mini skirt in the mix.