Dating Tips7 minutes Marie, 14 March 2023

What to wear on a first date

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Though you’ve been here before, the thought of a first date is at once exciting and daunting again. You’ve read each other’s online dating profiles. You’ve probably exchanged a few messages. But this is the first time you’ll meet face to face. You want to look good on your date. You want to make a good first impression but not at the cost of your comfort. So, let’s pick out an outfit that makes you look good and feel good too. Here are some of the best clothing ideas.

Is your outfit really that important?

Paying attention to how you look isn’t shallow. It shows that you value your date enough to make an effort for it. You’ve probably seen pictures of each other on the Even dating app. Still, your outfit and how you carry it will influence the impression you make on your date. You want your date to be attracted to you and yet respect you.

What’s more, when you like the way you look and are comfortable, you feel more at ease and confident. It’s a winning formula for a good first date. This holds true for men as well as women. Show your fashion, your style and yourself.

Choosing the right outfit

Whether you’re 16 or 36, getting ready for a first date will give you butterflies. The ideal outfit depends on where you are going and what you’re doing on your first date. Let’s take a look at the outfits you can wear for different types of dates.

Outfit ideas for a daytime date

Daytime dates are ideal for single mothers. These dates have a casual vibe so you must dress accordingly. When you’re picking an outfit, think of where you’re going, the weather and the image you want to portray. Here are a few ideas you will love for the day:

  • A stylish blouse with a well-fitted pair of jeans
  • A midi dress
  • A flowy skirt with a colourful blouse

A pair of comfortable flats work well with all of the above as well as a pair of low heels. Though you may have planned to drive to your date and back, make sure your footwear is comfortable enough to stand up to an impromptu romantic stroll.

Now, let’s accessorize. Think of this as a way to show off your personality. Do you like chunky earrings? Layered necklaces? A fun handbag? Choose accessories that make a statement without going overboard.

Dads, you need to make an effort too. Dress up a pair of denim jeans or chinos with a smart button-down shirt. Rolling up the sleeves will give you a casual, edgy vibe. You can’t go wrong with this combination.

Dressing up for an outdoor date

If your date involves outdoor activities, practicality and comfort must take precedence over style. That said, you still need to make an effort to look good. A pair of well-fitted slacks, leggings, or high-waisted jeans that flatters your curves is a good option.

Women could pick a colourful, feminine top to stand out. Solid tops give you a sporty appeal while prints can add energy to your outfit. If the weather is cooler, you could layer it with a shirt or a light jacket.

A collared t-shirt or a sweatshirt with hiking pants works well for men on an outdoor date. Just be sure to skip the cargo shorts.

Always wear comfortable sneakers and minimal jewellery for outdoor dates. You can accessorize your outfit further with a cap and sunglasses. These serve a practical purpose while also showing off your adventurous side.

What to wear: date night in a fancy restaurant

Dinner dates demand dressing up a little more. Your choice of outfit depends a lot on the type of restaurant you’re going to. If your evening involves fine dining, here are some clothes you could wear:

  • A modest version of the classic little black dress
  • A pair of trousers with a pastel blouse
  • A skirt with a top and a blazer

Accessorize these outfits with delicate jewelry, a pair of black kitten heels or strappy sandals and a chic handbag.

Men on a date at a fancy restaurant don’t need to wear a three-piece suit. That said, formal trousers and a crisp shirt will make a striking first impression. Make sure you’re wearing a smart watch and a belt and shoes that complement each other.

Casual dinner date ideas

Dinner dates don’t always have to be fancy. Pubs and bars are popular first date venues for single parents. The right outfit gives you a look that is polished, chic and relaxed. Here are a few ideas:

  • A stylish skirt and top
  • A printed knee-length sheath dress
  • Well-fitted jeans with a blouse that adds flair in the form of details such as subtle cut-outs, ties and lace

You can wear a pair of small heels or flats and complete your outfit with a sling bag or tote. When it comes to jewellery, pick a pair of statement gold earrings or a bold neckpiece.

Classic outfits you can’t go wrong with

First dates don’t have to fall into one of the above categories. You may choose to enjoy a cup of coffee together. Or, have a picnic in the park. Get competitive at a gaming arcade or swing by an art gallery. Here are a few classic date outfits that would suit almost all your plans:

  • A pair of denim jeans and a blouse and a blazer
  • A printed knee-length dress
  • Trousers with a fitted top and a shrug/ blazer

Perfume and makeup

An outfit is incomplete with a splash of perfume. If you have a scent you love, this is the time to wear it. There aren’t many do’s and don’ts when it comes to perfume except for the obvious; don’t go overboard.

Makeup is a matter of personal preference. Ideally, give yourself a soft, natural look. Choose between enhancing your eyes or your lips depending on which feature you like more.

Along with choosing the right outfit to wear, date nights deserve special attention to your grooming. A stubble isn’t likely to impress a woman neither are unkept eyebrows.

What not to wear, date outfit do’s and don’ts

Irrespective of where you are going, you don’t want to send out the wrong message with your date outfit. So, here are a few points to keep in mind.

  • Firstly, make sure your outfit fits you well. You don’t want to wear a top that you need to constantly adjust or a skirt that needs to be pulled down every few minutes. At the same time, your outfit shouldn’t be frumpy.
  • Avoid wearing anything too revealing. An off-shoulder top is flirty while a tube top may show off more than you want to show off on a first date. Keep the one-skin rule in mind when you’re choosing your outfit – if you’re flaunting your shoulders, keep your legs covered and vice versa.
  • Avoid loud patterns. You want your date to pay attention to you, not be distracted by what you’re wearing. Instead, stick to solid colours or simple patterns. You can mix a solid and a print, but avoid mixing 2 prints.
  • Make sure that your outfit is not torn or damaged in any way. You may try to hide the tear but if it is noticed, it’ll leave your date with a poor impression of you.
  • Skip the stilettoes. On your first date, you want to concentrate on your date, not flexing your toes. Of course, you don’t want to twist an ankle either.
  • Lastly, being comfortable on your date is important, but it’s no excuse to wear sweatpants. That would make you come across as sloppy and lazy. There are plenty of other casual trousers you probably have in your wardrobe. Pick one that keeps you comfortable while making sure you look smart.

If you don’t have anything that feels quite perfect for your date, it might be a good time to go to the shop and invest in something new.


Jeans paired with a beautiful blouse and a blazer are a great option for a first date at a casual venue. It goes without saying though that ripped jeans or distressed finish jeans are never a good idea.
Anything that fits well and makes you feel confident in yourself will create a favorable impression on your date. That said, dress for the occasion and avoid anything ill-fitting or too revealing.
A casual outfit of jeans or trousers with a stylish top is ideal for a concert. If you’re a fan, band tees are a cool choice for men and women.
Dating as a single dad, your outfit and shoes should match the venue. Loafers or sneakers are a good choice for daytime dates while boots or polished leather shoes are good for a formal date.
Picking the perfect first date outfit comes down to finding what makes you feel most confident. If you’re not comfortable in a dress, swap it for a pair of pants. Wear an outfit that you wouldn’t think twice about. After all, you want your date to like you for who you really are.
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