What To Wear For Dinner Without Looking Classless

It’s the first date and you want to leave a good impression on him. You want to show that you’re a classy, high-value woman. Perhaps he is the man of high status that you want to impress – without giving it all away and showing him that you’ve been thinking about this outfit for a while…

In a society where ladies get slut-shamed for anything, we unfortunately have to be very conscious of our clothing. What you wear is indicative of who you are, even if that’s not entirely true. But in our world, that’s how it works. So we need to be smart and strategic. A first date with a high-calibre man has to be very thought through, and you can’t just quickly grab the first best thing in your wardrobe. Men are very visual and people and are wired to be judgemental.

the.la.way with an elegant dress


(This outfit is perfect. While the dress is “short”, it is covered on the chest, and the flared hem gives a feminine appearance. A perfect idea for a first dinner date)

One of my hobbies is to pick men’s brains and understand how they think. I’ve been lucky to encounter many men who have opened up to me on so many topics, giving me amazing juicy content to write about. One topic that is extremely interesting to look at is what women wear and the male perspective.

You see, I’ve discovered through my male research that men have A LOT of opinions on what women wear.

You might think they don’t have a clue because they are not fashionistas themselves, but they actually do! Men describe how off-putting it is when women try too hard and dress vulgarly. They also told me that it’s never nice when women try to complicate their outfits too much by being “super fashionable”. It seemed like what mostly made them interested was a combination of class, femininity and style. They want to be next to a woman they can feel proud of after all. Style and class will give just that, and the feminine touch is more for the sexual spark. Knowing how to dress elegantly and like a classy lady is powerful.

kristinalb_ in summer dress


Short dresses can be worn on first dates, but only if they aren’t bandage dresses or are very fitted. Leave some mystery!

There are so many great role models of feminine and classy ladies. Monica Belucci, Audrey Hepburn, Sophia Lorén and Amal Clooney are just some of them! However, not all women are shaped the same and have the same attributes so it’s important to find out what works for you and what brings out your most confident self. You have to be able to know how to make an entrance and walk confidently.

In the end, what makes a man interested is confidence. They want energy that will make them want more. Confidence is just that (as long as you don’t become full of yourself). The right outfit will give you that confidence where you feel like the best version of yourself! Perhaps some have the attitude too, but clothes do help a lot!

So what to wear on a dinner date?

The key points:

Don’t showcase your breasts, bums and generally too much skin, as that will just give the wrong impression. But this information is so elementary…

Avoid super fancy clothing and being overly dressed up. Don’t wear anything that makes it look like you’re trying too hard. The complicated fashion look should be left for your lunch with the girls!

Don’t come too conservative either. The Mother Teresa look is not sexy, and it feels a bit too staged. It’s almost like you’re trying too hard to prove that you’re something you’re not.

moldavskaya_v dressed elegantly at party


The color red signals passion and men tend to love it!

What to do instead?

  • Embrace your femininity, be sexy and more innocent and cute than being provocative and aggressive. Try being more ladylike.
  • If you have a strong personality, wearing something neutral and conservative is beneficial. If you’re the opposite (shy, laidback and timid) then going a little bit bolder in your outfit could give you that perfect balance.
  • It’s important to dress flirtatiously, but it has to be tasteful and not the main focus.
  • Wear a dress or a skirt for the occasion as trousers can easily come across masculine, unless you are savvy with your styling.
  • Since it’s an evening occasion, you want to dress up rather than dress down. If you are being invited to a more casual outing, then perhaps you should ignore these pictures for reference.
  • Wear something you honestly feel comfortable in. You don’t need to be a psychic to see if someone is not 100% at ease and it might reflect on the date, making it awkward in some ways.
  • Depending on who the man is, the clothing can vary. If the affluent man you’re going to meet is more hipster/urban/trendy then many of these outfits might not work for him. The point is not to be a doormat and only please the man, but to find a balance between what is YOU you and what makes him tick. Always dress in a way that you feel is your style and work around the rest. Finding a middle ground is usually the best way to go!
  • If you really feel like you’re struggling, then “the little black dress” is a safe bet. It’s what I personally used on most of my first dates.

Here are some outfits I think are very “date proof”, meaning you can’t go wrong wearing something like this. Most of them carry a good mix of feminine, flirty, chic and classy, which will leave a positive impression on any man!


The colour of passion, red, plus a covered chest and a beautiful skirt. It’s giving a feminine feel.

leylamilani in a blue dress at a party


Another dress that can be shorter if it’s not very fitted and a little bit more covered.

silviabraz dressed for a party


Perhaps not the sexiest shoes, but the dress is feminine and beautiful to look at. Very figure flattering!

vika.d.evil in an elegant black dress


Another Skater dress variation, with long sleeves but a shorter skirt that leaves some mystery.


Dresses with a “flow” and light materials will always work because they feel very romantic.


A classy, subtle colour and neutral type of dress. Not too sexy but not too conservative. Just perfectly fashionable!

_alena_alena_ dressed in white


This is a perfect dress for a dinner date. You give a little bit of leg or cleavage without giving away more than just that. Very classy and works on all body shapes!


  1. Alexandra
  2. Cheryl
  3. rose