Style Guide: How to Dress for Date Night

Get Ready For Date Night

From nerve-racking first dates to an outing with your longtime partner, find date night dresses for the occasion!

With dressing for anything, the first rule of thumb is to match the formality of wherever you are headed! For a date, you want to also make sure you are comfortable, confident and that your outfit perfectly reflects who you are. Ease stress and worry by knowing what you are going to wear for your next date. And even better, we are here to help! From a simple elegant evening dress to a casual date night outfit, we picked out our top date night dresses and put together some outfit inspiration.

Top 4 Tips on Dressing for a Date

When you’re dealing with first-date nerves, the last thing on your list of stressors should be your outfit.

  1. Comfort is key: Pick a date night outfit that not only looks great but also makes you feel great.
  2. Know the location: Do some research on where you are going so your evening outfit is styled according to the vibe of the venue.
  3. Check the weather: If it is going to be hot, don’t wear something that might make your nervous sweats worse, and if it is cold, bring an added layer for your evening outfit!
  4. Don’t wait until the last minute: Planning your date night outfit ahead will ease stress and won’t result in the contents of your closet being spread across your room.

Coffee & Pastries Casual Date Outfit

Nothing sparks romance like a soul-searching conversation.

The Kelly floral maxi dress is the perfect effortlessly chic look! Pair with a white crossbody bag and flat white sandals for a clean and simple look.

For the more personal dater, coffee and pastries is an intimate affair, where casual date night outfits are perhaps the most important. You're going to find yourself in a more up-close-and-personal encounter, and your outfit should be so comfortably cute that it's the last thing on your mind - and the first thing on theirs. Choose a daytime appropriate style that shows you woke up in the morning on the right side of the bed!

Daytime Casual Date Outfit

A daytime date requires "casual comfort."

The Jori tie-front jumpsuit provides the right amount of function and flattering. The perfect regular and plus size date night outfit. Pair with gold jewelry and black accessories, and don't forget your sunnies!

Whether you’re going for a stroll on the beach, going out for lunch, or having a picnic in the park, choose comfort. Look effortlessly chic in a casual date outfit that does not skimp on style. Express your personality with your accessories and spend the day feeling confident in your casual outfit with little to no stress. You definitely won’t regret picking an outfit that does not require constant attention.

Day-to-night Date Night Outfit

With so much power, comes so little time to change.

The Diana floral bodycon dress is simple with a pop of color! Pair with our Talula black shrug, a black kitten heel, and silver jewelry.

We love our boss ladies, but sometimes this leaves very little time - or availability - to swap outfits before the big date! Instead of bringing a whole new outfit with you to the office, wear an appropriate work and date night dress. Just focus on switching out the accessories and shoes! Go for a classic and simple date night dress style that features an eye-catching print that you can downplay for the day and jazz up at night!

Cocktail Hour Date Night Outfit

Drinks may ease the tension, but this short encounter leaves little time to make an impression!

The Sari chiffon crossbody dress incorporates sexy, flattering details while still being comfortable. Pair with an off-white bag and leather mule to complement the mandarin orange. 

Libations and conversation are a staple date for many reasons. Our favorite? We can pull out our favorite pair of high heels, look like a knockout, and within hours throw them off! When picking cocktail dresses, choose a simple elegant evening dress with a statement detail. Short and flirty will also always be an excellent accompaniment to a classic martini or virgin margarita.

Best date night styles, according to you!

Shop dresses for date night & beyond

We hope you've reached the end of this article and let out a little sigh of relief!

Terri is wearing the Lisa mandarin wrap dress in a size 8.

Dressing for a date night can be challenging. While you may feel the pressure to go with a trendy and chic look, it is also important to feel comfortable and confident. Before getting ready for your next date, make sure to keep these few tips in mind:

  • Pick a date night outfit that makes you look AND feel great!
  • Consider the occasion, location, and weather.
  • Ease pre-date jitters by planning your date night dresses ahead of time.
  • Let your personality shine through your evening outfit!

Whether it's the promise of something new, or the kindling of something old, dress to impress! There is nothing better than getting all dressed up for a date out and feeling just as confident as you look. Get ready for your next date night by shopping our curated collection of date night dresses and jumpsuits below. From regular, to petite, to plus size date night outfits, we have a lot to choose from!

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