Dressed to Impress and Find Love: Date Night Outfits

If you have a date coming up, you’re probably excited and anxious at the same time. Excited because this could be the ONE (aka the love of your life); anxious because what are you supposed to wear?

Date night outfits (whether it’s a first date or your third winter date) can be tricky to plan. You want to wear something that makes you look good, feel confident and hopefully, attract the attention of the person you’re going out with.

Unfortunately, there’s no one-size-fits-all solution for this concern, but there are a few things you can do to create a killer outfit that stuns your date.  From wearing romantic dresses for a first date to rocking a jacket with fake fur for winter date nights, here’s everything you need to know.

How Should I Dress for Date Night?

Choosing the right clothes to wear is a struggle — that’s a fact. But it need not be a cause of date night anxiety.

Instead of fearing the process of dressing up, creating your date night outfit should be an adventure. Dress up according to the occasion! Experiment with the clothes in your wardrobe. Consider the following ideas for the following occasions.

First Date Night Outfit

Anyone who has been on a first date knows the pressure of wanting to strike a good first impression. To pull off a successful first date outfit, strike a balance between looking casual and polished, chic and feminine. Wear something dressy but not too uptight. How about a stylish top and skirt worn with medium-high heels? Clothes adorned with soft florals, lace and simple ruffles are also great options.

Remember: the best first date outfit is the one that keeps you looking clean but not too structured. Impress your date with light-colored clothes in soft tones.

Summer Date Night Outfits

Looking your best can be a bit tricky when you factor in a layer of summer heat (and the sweating). Who wants to deal with sweaty thighs or pit stains when they’re trying to impress someone anyway?

To avoid these summer date night mishaps, it pays to prepare. For example, if you’re going to a rooftop bar, impress your date in a fuss-free midi dress colored in summery hues. Complete the look with your favorite earrings and some heeled sandals.

If you’re going to a casual date night (e.g. a baseball game), feel cute in an outfit composed of your favorite denim shorts, cropped tank, a baseball hat, belt bag and some sneakers. For a picnic date, wear some linen pants to stay fashionable and comfortable. Make the moment better with a monochromatic top, a straw bag and some slide sandals.

Winter Date Night Outfits

When it comes to winter dates, “cozy” is your keyword. You want something cozy and fashionable. What you don’t want is to look fashionable but freezing.

For casual winter dates, the dress code is functional and fashionable. Wear an elegant belted coat and a cashmere sweater for your next date. Create a foundation for your look with a classic black sweater then layer the look with a long coat. This will give your winter ensemble more texture while keeping you warm. Cap off the look with some over-the-knee boots and gold hoop earrings.

Fall Date Night Outfits

Unlike summer and winter, the autumn season falls smack between the “Warm or Cold” spectrum. However, the clothes you wear during fall are more forgiving, and this thought applies to your date night outfits.

Match the season with a silk top, moto jacket, dark jeans and your favorite shoes. If you want to look sexy, why not wear some strappy heels? But if the weather is cold, try stiletto boots or some pumps.

How Can I Look Attractive on a Date?

Man in Gray Suit Standing Beside Woman in Green Dress
How do you look your best for your date? (Photo by Juan Vargas from Pexels)

If you don’t have occasional pieces in your closet, fret not! There are plenty of ways to perfect your date night outfits without going overboard and rummaging through the depths of your wardrobe. To nail your date look, just remember the following tips:

Wear Something That Makes You Feel Confident

The best date night outfit is the one that makes you feel your best. It sounds cliché, but the old saying that “When you look good, you feel good” is true. The link between what you’re wearing and how you feel about it is called the theory of enclothed cognition.

A 2012 study from Northwestern University reported that clothing could alter a person’s psychological state and improve their outlook and performance. The researchers conducted an experiment where one test group wore the iconic white lab coats of doctors (a garment associated with carefulness and intelligence) while another test group was instructed to wear plain clothes while doing attention-related tasks. The group that wore the white lab goats did better on the tests.

Applying the theory of enclothed cognition on your date night outfits can influence your subconscious, as well as your date’s. So, go ahead and wear clothes that make you feel more confident while you flirt.

When In Doubt, Wear Black or Red

Black and red are romantic colors and can make you look more desirable and attractive to your date. Subconsciously, we associate the colors with romantic items and events like lacy lingerie, roses and Valentine’s Day.

Science also backs up the black-red color theory. A 2008 study from the University of Rochester reported that the color red enhances a man’s attraction to a woman. It made them “feel more amorous” towards the opposite sex. The report also stated that men were willing to spend more on women who wore red on their dates.

In 2018, another study involved 600 people participating in “First Dates,” which was a reality dating show in Britain. The study found that black was the most popular color for first date outfits, regardless of the wearer’s sexual preference or gender. Though considered the “safer” alternative to red, black helped wearers still look more attractive and fashionable.

Steer Clear of the Browns and Oranges

Knowing what colors to wear on your date is helpful but knowing what you shouldn’t wear is equally important. According to color psychologists, brown and orange clothes shouldn’t be an option for date outfits and interviews.

It all boils down to color psychology. For instance, orange is a color that calls attention. It is a color used for safety gear, construction cones, and caution signs. When you wear orange, you’re subconsciously sending signals that you could be attention-seeking, superficial or arrogant. On the other hand, brown is considered “too basic.” It can make you appear overly serious too. If you want to incorporate brown in your outfit, why not use brown accessories instead?

Show Off Your Neck

Most people believe that showing off your chest is one of the best ways to catch your date’s attention. However, showing too much cleavage might hurt your chances of finding love. Women who wear outfits that reveal too much are often perceived as promiscuous and superficial instead of seductively sexy and demure.

Avoid wearing super low-cut dresses and tops to not appear as “Just a One Night Stand” material (unless this is your intention). Instead, draw more attention to your neck and shoulder area. Your neck is one f the most romantic areas of your body that isn’t too sexy. Emphasize this part of your body by wearing off-shoulders or sleeveless tops. Also, sweep your hair to one side to emphasize the slender shape of your neck.


Date night is one of the best nights to bring out your best self. Impress your date by taking these date night outfit tips by heart!


Nadav Berenstein is a real estate developer by profession and a chess player by heart. A member of the International Chess Federation and the Euro-Asian Jewish Congress, Nadav has been playing internationally for several years now. When he's not playing chess physically, you can see him sharpening his skills online at Chess.com Aside from chess, Nadav also enjoys playing Magic the Gathering and traveling the world.

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