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6 Simple Rules for Picking a First Date Outfit

There are very few things that can make a lady nervous as much as a first date. A lot of what could go wrong comes to mind, especially if your date is that guy you have had your eye on for some time.

“What if he turns out weird? What if we don’t connect? What if I realise I don’t actually like him?”, all of these are questions are likely to run through your mind. However, these are possibilities that you cannot control, and worrying about them will not help. What you can control instead is how gorgeous you can make yourself on the day, and this includes picking the right outfit.

There are so many rules about what to wear on a first date that it can be difficult to determine the good from the bad. However, the best option is usually what makes you feel your best. That being said, you can also get inspiration from these tried and tested rules for choosing a first date outfit.

1. Your personal style is always best 

You may be tempted to follow popular trends, and wear one of the in-vogue outfits. However, a first date is not the best time to experiment with the latest trends unless you absolutely want to. In that case, it’s best to follow your gut.

That being said, it is always best to wear what you are comfortable with on a first date. Of course, the plan is for the date to lead to something special, and while you should go out of your way to look your best, a first date might not be the best time to try out the latest runway fashion. Don’t drop your style for a stranger, nor should you go overboard.

2. Dress to be comfortable 

I always advise against wearing heels on a first date. Apart from the obvious discomfort, especially if you are not used to it, it is easier to gauge the difference in your heights if you are wearing something flat. If you feel uncomfortable after getting dressed at home, chances are you will feel terrible all through the date.

Whatever you eventually settle for should be something you have tried on before, and feel completely comfortable in, this way, you will feel more confident. After all, you never know how the night will go, and you may need to leave in a hurry.

3. Be sexy, with the promise of more 

You don’t want to arrive for dinner at a jazzy club looking like Jessica Rabbit, but you also don’t want to arrive looking like Mrs. Grundy. Dress sexily, but don’t give everything away on the first date. Keep him guessing.

If you are the dress type, wear a sexy slip dress, but tone it down a bit with some simple accessories. And if you are the jeans type, a simple yet sexy top like this Gauze Reversible Joanne Top from RachelPally.com will do just fine.

4. When in doubt, less is more 

If you can’t make up your mind what your look to a first date should be, follow the tested rule that less is more. This doesn’t mean wearing little clothes, more like being a little more neutral. I’m talking light makeup, casual accessories, and maybe a little bit more lipstick to give your face colour.

One thing I have discovered when it comes to outfits is that you can never go wrong with white on black or vice versa. I am referring to a white silk blouse on a black skirt or leggings. This minimalist look is always sexy when combined with the right amount of makeup, and the right accessories.

5. When in doubt, go with your favorite 

If you can’t decide what to pick for a first date with a new beau, just wear any of your favourite items. I mean, you can never go wrong with something you know and love, and you will actually feel more confident than if you had rushed to pick an outfit off the rack.

If you must wear something new, let it be a part of your outfit that will not undermine your confidence or looks. For instance, you can grab a coloured silk scarf to accessorise your outfit. Picture a red silk scarf riding on a white silk blouse, or red shoes with a white and black combo. It works every time.

6. Avoid overambitious styles 

A first date is not a life or death situation, so you don’t have to overthink or over-plan it. This means avoiding overly ambitious or complicated styles. As a matter of fact, you can go for a first date immediately after your normal day without going home first. It’s simply a matter of leaving your jacket at the office and putting on fresh makeup.


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