Date nights can be stressful. Especially early on, it seems like every little thing will send a specific message, and nobody wants to be misunderstood. While your talking and behavior will hopefully keep everything crystal clear, there’s no denying that our style and outfits always put out signals of their own

In general, your fashion goal should be to feel comfortable and confident — on a date or anywhere else. But it’s also important to dress with an eye for the event, location, setting and another person.

Of course, it doesn’t help there are so many choices from which to choose. One look into your closet will remind you that the possibilities are almost endless. Then again, the following outfit tips and techniques can help you decide what to wear on your next date night.

1. Fancy Casual

The last few decades have been about the whole world rewriting the rules of fashion. One great outcome has been the ability to now pair together once-contradictory items. You don’t want to go too far, but one great look is wearing a blazer over a simple T-shirt. Going with a classic white or plain-colored shirt is popular. But you can even wear one that’s ironic or a bit more playful. Or, flip it and wear a patterned or flora blazer. Whichever you choose, with a look like this, you can fit in almost anywhere.

2. Dress for Any Occasion

Trends come and go. An outfit that might have been the height of fashion five years ago can look lame today. On the other hand, some things never go out of style — and you can never go wrong with a little black dress for any occasion. Dress it up when you’re going to a fancy restaurant or dress it down with your favorite accessories on a casual outing. No matter what, this can be the perfect look for your date night.

3. Cute and Comfortable

What’s another thing that never goes out of style? Jeans. It may seem too normie to wear on a date, but there really is nothing wrong with wearing some clean, crisp Levi’s and a sweater. This can be especially good if you’re on a first or second date and want to keep things light. This way, you won’t project anything other than: “This is me.” Sometimes, that’s the only message you need to send.

4. Stay on Your Feet

The last thing to consider carefully is your footwear. Perhaps more than anything else, the shoes you wear will project a different message. Fun sneakers, like custom Chuck Taylors, suggest you’re looking to keep things more casual, while two-inch heels might tell your date this is a more significant encounter. Naturally, you know best what you want to tell the world. But going with something in the middle — not too casual, not too elegant — is often the best route.

Date Night Tips to Dress for Success

The most important thing about any date is leaving the house feeling confident. It’s the connection and conversation that matter most. But let’s be honest: We all want to look good, too.

To do it best, try pairing together something casual and fancy. There’s also never anything wrong with classics like a little black dress or some old-fashioned jeans. And don’t forget to think about what you put on your feet.

Dinner and a movie? After-work drinks? A simple cup of coffee? Cooking together at home? Those decisions can definitely be tough. But these tips will help make sure that, whatever you decide to wear, at least your style will never be in doubt.


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