With half your wardrobe strewn across the floor, we all know that picking the perfect casual date night outfit is no easy feat. Everyone wants the same thing when it comes to dressing for a date - they want to look confident and cool, sexy, and stylish - all without feeling like they are terribly uncomfortable, self-conscious, or looking like they tried too hard.
It often seems that appearing effortless takes a lot of effort indeed.
Fear not, we are helping to take the emotional effort out of choosing that perfect date night outfit by bombarding you with some beautifully simple ideas that are guaranteed to keep you cozy and cool and able to bloom into your best self. Whether getting dressed up for Valentine's Day with your beau or choosing a get-up for that casual wine night at home with your significant other, here are the date night outfits we are pulling out of our closet this season...
Cute Date Outfits With Jeans
Sexy Pullover and Jeans
Why it works: From cowboy ranch to the catwalk, there is no wardrobe staple in the world that can compare to our absolute unbridled love of jeans. There are few items that ooze laid back confidence quite like the jean. Warm and practical, hardwearing and with a pinch of attitude, wearing a well-fitting pair as a date outfit is all about owning it. There are also tons of different styles out there; from slouchy boyfriend jeans for that walk in the park to sexy black jeans that hug all your corners for drinks at the bar, pairing a sexy pullover with jeans just screams cool, causal, and completely in touch with your own sense of style.
How to do it: So many jeans means you can pick a pair that suits your comfort level. We love the slouchy boyfriend jeans paired with a backless pullover. Pick a sweater in a pale and light feminine color for a gorgeous contradiction. It’s these outfit details that will make your dates head spin.
Sexy Top And Jeans
Why it works: Just because you are slipping into a pair of denims doesn't mean that you can't be sexy as hell. Among the many things we love about jeans is the fact that they can be dressed up or dressed down in seconds flat. Sure, you can Netflix and chill in denim, but you can also put together your skinny jeans with a sexy crop top and be more than ready with a date night outfit that is designed to make the whole room swoon.
How to do it: Want an award-winning outfit formula that cannot miss? Pair your high rises with snappy ankle beats and a shorn crop top that shows just a slip of skin (no belly button) and throw over a leather jacket, moto jacket, or even casual-chic black blazer if you get cold. The beauty of pairing casual pants with dressier heels and a hot top is super suggestive of having many different facets to your fine personality. We also love switching this look on balmy bright nights for white jeans and kitten heels for an ensemble that captures the essence of al fresco cocktails, jazz, and tapas on a summer date night.
Casual Date Dresses
Flirty Sweater Dress with Boots
Why it works: Leave the little black dress behind and say yes to a date night dress that keeps you feeling as comfy as can be. A dress doesn't need to be a full-on formal affair. Choose something soft and cozy in cotton or even a short sweater style mini dress paired with leggings and boots. Dresses are always a good go-to for date night outfits that leave their mark. They are feminine, cute as hell, and guaranteed to make you feel fabulous.
How to do it: We love fun sweater and tunic dresses that are hemmed in at the waist and flared at the skirt. Remember the sweater style dress is all about being chic and cozy so make sure you choose one with soft and cute details like a couple of buttons on the front or angel sleeves. Pair with chunky combat boots for a side of pure attitude or for the more feminine grown-up approach, pick an ankle boot with a low heel. Depending on the season you can bare those soft and sumptuous legs or you can stay warm with a pair of leggings or tights.
Long Midi Dress With Jean Jacket
Why it works: Summer date nights call for a simple slip dress that makes sense whether at the movies or out on a dinner date dining beneath the stars. Summer dates are all about picking date night outfit ideas that don't turn you into a sweaty and uncomfortable hot mess. With the long midi dress that falls just above the ankle in a sheer soft fabric and pretty feminine pattern, you can be sure of looking cool and flawless throughout the night.
How to do it: Choose a flowing midi dress in comfortable cotton that doesn't cling. For those who are concerned about spending the evening shivering, the long midi dress will cover bare legs and you can easily pair with a casual denim jacket either cropped or moto style depending on your look. You can pair the midi dress with chunky boots for a gorgeous funky look or stick to slip on pumps or low-heeled shoes.
Cropped Tops and Casual Trousers
Cropped Top and Tack Pants
Why it works: For those looking to play it super cool when picking their casual date night outfits, the pairing on a cropped top and tack pants is as Instagram worthy as it gets. The crop top is one of the must-have fashion items of the year and is all about showing just a hint of skin and reclaiming your body space. When paired with tack pants you have a look that is urban chic, sporty and is already blowing up lookbook.
How to do it: Tack pants are all the rage - you can choose a pair that has a hint of athleticism or if you want something with a pinch more bohemian grace, go for tack pants that have a hint of yoga girl gorgeousness AKA a drawstring waist and slightly baggier fit. Paired with a cropped top in simple black and white and with sneakers you are dressed to dance up a storm at a concert or you can even be bold enough to pair with sock boots for a look worthy of even the best fashion blogger.
Midi Skirt and Cropped Top
Why it works: Calf grazing skirts are forever sexy which is one of the reasons why we love them. The other reasons include them being versatile enough to wear with anything, incredibly comfortable when choosing a cozy material, and super flattering to boot. Carve out a glorious silhouette for yourself by pairing with a cropped shirt and you have a look that will take you all the way to the top of the date night success charts.
How to do it: We love cozy midi skirts that are just fitted enough to hold shape but not so clingy that they could encourage feelings of self-consciousness. Pick a bold feminine color and pair with a cropped top or even a shorn t-shirt that accentuates your figure. You can wear this for just about any occasion if you swap out the style of shoe (sandals for peachy beach walks, kitten heels for dinner, and ballet pumps or sneakers for casual nights strolling around town. The rule of thumb when wearing midi skirts is to balance out volume and proportion - slouchy on the bottom, tight on top and vice versa.
FAQ About Dressing for a Casual Date Night
What do you wear to a casual date night?
Leave the minidresses and ball gowns at home, a casual date night calls for outfit inspiration that makes you feel a million bucks based on comfort level and cuteness. From jeans and slip tops with a blazer to a knit dress and ankle boots, and even a loose-fitting jumpsuit, the aim of a great casual date night outfit is to mix cozy and chic items together with just a hint of statement style.
How do you dress casual and flirty?
Mix it up! We love the casual flirtiness of wearing delicate slip dresses with biker boots or boyfriend denim with backless sweaters. Show just a pinch of skin - for example, if wearing a short denim skirt opt for a long-sleeved loose shirt or if you are going for a midi or maxi skirt pair it with a cropped tee that showcases a slip of stomach and your arms.
Is it OK to wear jeans on a first date?
Totally, with a thousand different styles out there you can choose high waisted cropped and pair with a blazer and ankle boots for casual-chic or opt for black skinnies and a loose top for that rock star goddess look.
What should you not wear on a first date?
Honestly, we say wear what you love, wear what makes you feel comfortable, and wear all the things that you believe captures the unique essence of you. We would suggest steering clear of outfits that don't make you feel amazing as the last thing you want on an already high-pressured situation is to be super self-conscious and questioning your life choices (including what to wear). Basically, wear the looks you love and let your love life take its own sweet course.
What are your casual chic options for date night? Share your must haves with us in the comments.
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