Whether you have been with your partner for years or are meeting a new someone, it feels so good to get dressed up for a date. From your heels to your accessories, every detail adds up to make you feel your best. No matter where you are headed, get dressed in an outfit that is sophisticated, chic, and most importantly, comfortable. We’ve rounded up some inspiration for your date outfit with the timeless styles below, which can be worn for a candlelit dinner, drinks on a rooftop, a picnic in the park, and beyond.


A Twist on Tailored Pieces

A woman wearing a blazer, skinny jeans and Julieta block heels.

If you are planning to go directly from the office to date night, a flowy patterned blouse with a pair of tailored trousers is a lovely choice. When it comes time for your date, a few simple adjustments will turn your professional look into a more relaxed one. At the end of your workday, add a small clutch with shine and some jewelry with sparkle to jazz up this look. You will be wearing your heels all day and in to the evening so make sure that they are comfortable.


The White Trench

A woman wearing a white trench coat, skinny jeans and brown Julieta heels.

Sometimes a casual date can be harder to dress for than a formal one. The difficulty is in finding a balance of appearing relaxed, yet pulled together. A pair of sleek skinny jeans with a statement sweater might not speak volumes on its own, but when you add a white trench, you are sure to turn heads. While you can wear flats with this look, a pair of heels in a neutral blush will add another level of sophistication and elevate the outfit. Keep your jewelry to a minimum.


The Urban Ballerina

A woman wearing leather shirt and skirt, black tights, and Julieta heels.

You can never go wrong with an all-black ensemble for your evening plans. Black is inherently stylish, flattering on every body, and gives you an air that bolsters confidence. A little black dress may be the simplest choice, but lately, we’re loving separates like this blouse and skirt duo. The sheer sleeves on the blouse paired with the leather skirt are subtly sexy without being in your face. Black tights and black heels create a leg-lengthening effect while a graceful bun completes this ballerina-inspired look.


All That Glitters

A woman wearing a pink sequin dress and Julieta heels.

There are some formal dates where you know you will need to pull out all the stops. Having a date to an occasion like a New Year’s Eve party or a black-tie wedding gives you the opportunity to sparkle in a fantastic sequin dress. More is more when you’re wearing sequins, so go ahead and add a pair of dangly earrings to your ensemble. If dancing is on the menu, and it almost certainly is, then make sure your heels are comfortable!


Artsy and Sophisticated

A woman wearing black cutoff skinny jeans, a gray shirt and Julieta block heels.

Meeting your love at a trendy bar or art gallery? This stylish outfit will be the perfect compromise between casual and trendy. While neutral in color palette with a grey top and black pants, this look stands out from the crowd with statement shoes. As the rest of the outfit is muted in color, a pop of red lipstick is the best complement to this look.


Polished Perfection

A woman wearing a pink and cream skirt suit and Julieta block heels.

For a more formal date, like a glamorous evening at the opera or ballet, take the opportunity to dress up in a gorgeous statement dress that you don’t get to wear very often. When you are wearing a truly unique piece, like the coat dress featured here, let your shoes and accessories stay simple so as not to clash or take away from the main attraction. No matter where you’re going, this sophisticated ensemble is sure to impress.


The Carefree Midi

A woman wearing a brown and white striped dress and green Julieta heels.

Charming and comfortable, a midi dress with a pair of classic heels is an ideal date outfit no matter where you are headed. According to color psychology, red is a bold color that will empower you, so it is a great choice to wear when you need a boost of confidence. A pair of beautiful heels, whether deep brown, light blush, shimmery black, or a pop of color will ground this floaty outfit.