Dress to Impress: Casual and Cute Date Night Outfits

Parker Johnson

Posted on February 24 2022

Dress to Impress: Casual and Cute Date Night Outfits

Are you sorting through your closet, anxiously trying to find that perfect date night outfit? Well, you can stop that now, because we’ve got nine casual and cute date night outfit ideas for you right here. 

Whether you’re headed to a concert, dinner, or movie date, Hazel & Olive has you covered with versatile options that’ll help you feel and look your best. We’ve sorted them by season, so dive in and find the perfect outfit that’ll wow your date. 


Dress yourself up like a pro in these cute summer date outfits. Summer is a time to show off those legs with style and our outfit ideas do just that.


You can never go wrong with a flirty summer dress like this red Watch Me Bloom Dress. Depending on the occasion, it’s super easy to dress up in heels or dress down in sneakers. 

You can easily pair your cute dress with a denim jacket for an evening outing. Simply put, a summer dress is a perfect starting point to put together a pretty look. 

Oversized T-Shirt + Shorts

Couple this Howdy All Around T-shirt Dress with Hazy Daze Denim Shorts and your favorite boots, and you’re ready for that concert date! You can even size up your shirt for an oversized look or to wear it as a dress. Whatever you decide to do, this casual and cute date night outfit will keep you comfortable for hours.


Fall is a fun season to layer up and look fab. We’ve got a few nice fall date night outfits that’ll help you maintain your fashionista status. 

Sweater Dress

Sweater dresses are perfect to show off some legs, yet keep you comfy and casual. And if you’re looking for simplicity, this Camila Sweater Dress essentially makes up an entire outfit. It has a put-together vibe while still being casual. The cream color will blend beautifully with the fall season and can even be a great option for winter and spring!

Pair them with these cute Sunday In Spain Boots and you’re ready to dash out the door.

Shacket + Tank Top + Jeans 

This is a great laid-back fall date outfit that’ll achieve the wow factor without all the fuss. If you want to go for a grungy cute aesthetic, throw on a unique shacket over a tank top and light wash jeans. And depending on the date activity, you can easily pair this outfit with heels.

Dress + Shacket 

Pair your shacket with a simple dress like this Slip and Slide Dress for a more romantic look for a night out. It has a neutral khaki color that’ll seamlessly blend in with any shacket while complementing your figure. For shoes, opt for either a chunky block heel or sneakers. 


Dates during the winter months can be a bit tricky. You want to find something that’ll keep you warm without sacrificing style. Here are two winter date outfits that just might fit the bill. 

Knitted Sweater + Jeans or Skirt

Not all sweaters are created equal. Take this Knitted Knock Out Sweater for instance—it’s embellished with a cable-knit braided design that creates a chic and romantic look. 

Opt for either the Alex Jeans Acid Wash Wide Leg jean or In The Spotlight Denim Skirt for your bottoms. If you go with the latter, pair your skirt with tights and high-knee boots for a classic look.

As the cherry on top, throw on these gorgeous Double Hoop Earrings, which will complement your look with just the right amount of class. 

Pullover Sweater + Jeans

Ever heard of the French tuck? It’s a simple styling trick of tucking in only the front part of your shirt or sweater, which helps define your waistline while giving you a classy yet casual look. 

Take this cute Smile For Miles Pullover sweater for example. French tuck it into your acid wash jeans and put on Get Lucky Earrings. Clip up your hair into a messy bun with the Quick Fix Hair Clip. You then have a perfect outfit that speaks several languages—classy, cute, casual, and comfy!


Looking for something that’ll keep you not too warm and not too cold? Like winter, spring outfits can get tricky, but again, we’ve got you covered. The key is to keep your spring date outfit colorful and cute. Trust us, you’ll want to share these on the ‘gram! 

Feather Top + Jeans 

Feather tops are in. Fun, flirty, sassy, and sultry, this Brooke in Brooklyn Top is a statement that’ll knock your date out of their seat. Complement this gorgeous top with an equally gorgeous necklace plus denim jeans and voilà, you’re a walking piece of art.

Cardigan and Crop Top Set + Shorts

Go for a mod-inspired style with this Tara Cardigan and Crop Top Set. It screams spring but isn’t too loud to be distracting. It strikes just the right balance between fun and sexy. Wear this with your favorite denim shorts, skirt, or jeans, and you’ll be ready to rock this everyday look. 

Check Out Hazel & Olive’s Boutique Items

As you’re sorting through these outfit options, feel free to mix and match them. If you haven’t noticed already, at Hazel & Olive we’re pretty good at creating casual and cute clothes that are versatile and trendy. 

While you’re here, be sure to check out our latest new arrivals for additional date outfit ideas. We've got all the good stuff, from ruffled mini dresses to rodeo flare jeans. Don’t miss out! 

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