Nurturing Beauty Style Secrets Blog

What Do You Wear on a Date?

Despite the technology driven world we live in, there is still such a thing as an actual in-person date. While initially connecting by email and text (if that’s how it starts for you) there is no worry about how you look. Once you decide to meet in person, however, that is when the jitters start! How do you decide what to wear when it comes to such an already nerve-racking life event?

I have heard from too many women who say they almost dread the date because they can’t find anything they feel good wearing or that their bed is piled high with potential, but rejected, date options after an hour of trying things on.

I have also heard many times from women who want to feel pretty and even sexy on a date with their spouse/partner of 20 years. While a first date is obviously more anxiety-ridden than a romantic dinner with your long-time spouse/partner, the essence is the same: you want to feel special.

What do you do?

First, take a deep breath and keep reading. Here we three tips for creating your best first date outfit ever:

1. Be Comfortable and Be Yourself

It is sometimes easy to slip into the mode of feeling like you have to look ‘perfect’ or maybe you don’t want to appear to eager so you go to the opposite extreme to be super casual or you hide a little bit by wearing something nondescript and hope that your winning smile will make up for it. None of this feels comfortable or like the authentic you.

Once while presenting at a ‘dating’ workshop one of the women asked me on what date you are supposed to show cleavage. She wanted to be sure she did everything she was supposed to do. When I asked her if she felt comfortable revealing her cleavage, she said, not really. She thought that’s what men wanted and expected.

There was her answer.

No cleavage. She was not going to attract the man of her dreams by dressing in a way that felt insincere and distracting.

There is no absolute when it comes to how to dress for a first date except that you want to be comfortable, both physically and energetically. If she had worn a low cut top on a date she would have spent the entire time wondering if it was appropriate or too much (or too little) and would have been distracted by what she was wearing rather than feeling comfortable so she could concentrate on the personal connection. Not to mention that she would have been giving a message that was not authentic. Her true Mr. Right would miss the message and walk on by and she would spend any potential subsequent dates masquerading as someone she isn’t. That is not a good way to begin a relationship. It’s exhausting, if nothing else!

Remember, your clothes give your date visual clues as to who you are. Think about the statement you want to make.

2. Dress for the Occasion

These days first dates and beyond take many forms. I hear a lot about coffee dates—a quick, easy way to get a sense of whether this is someone with whom you want to spend more time. Who wants to be stuck for three hours with someone you don’t really care to talk to for more than 5 minutes and give up a precious evening as well.

Here are some ideas for what to wear to a coffee date:

Choose a pretty top. This one works on someone with delicate coloring and it also has a keyhole opening to give a hint of cleavage without being obvious:

Perhaps you prefer something with sleeves so you don’t have to worry about what to wear over a sleeveless top. In which case a pretty sheer top like this (with a cold shoulder opening) is casual and elegant:

Or how about a pretty summer dress:

You can also choose a tunic or dress that is too short and pair it with leggings and your favorite wedges, open sandal or ballet flat:

See more ideas for what to wear on a date (with commentary about how to or who can wear it) HERE.

You can see that there is a wide range depending on who you are. It is always critical to express your personality. Remember you want to attract the kind of person who will appreciate you for who you are. If you put on what amounts to a costume because you are trying to impress him or her then you are making false (not necessarily better!) promises. This is not just a ‘cleavage’ issue. If you are trying to be more sporty (to impress the ‘outdoor’ type) when you really prefer high heels or you love your cowboy boots but someone told you you have to be trendy and wear gladiator sandals, don’t succumb to those ‘shoulds.’ We’ve all seen those old movies where women were told that men were not interested in women who wore glasses so the women stumbled through the date not being able to see 2 feet in front of them just to entice the man. Yikes! Imagine keeping that up for the rest of your life.

What a lot of unnecessary energy expended when you will do much better being comfortably (and beautifully—however that is expressed for you) yourself.

3. Wear Colors that Make You Feel Beautiful

While it can be tempting to settle for being safely dressed all in black, unless that is truly your best color, choose something else. Yes, I know it feels safe and it can be slimming, but is it really expressing who you are? (And, black is not the only way to look and feel slim, if that is a concern for you. Read more about that HERE.

I recently ran into some friends from my yoga class at a local clothing store. There they were armed with their color palettes and totally dismayed by how much black surrounded them. These are sisters who each have a bright energy and if they dress all in black it totally squelches their natural vibrancy. Thankfully they each scoured the racks to find colors that matched their palettes and refused to settle for only black.

On the other hand, at the same dating workshop I mentioned above, there was a woman who had nearly black hair and wore a striking geometric haircut. She had a natural stately elegance with a sense of creativity. She said that people were telling her that she couldn’t wear the dramatic, black outfits she loved so much on a date. That it was too severe and would scare off any potential suitors. They suggested she wear softer colors and more drapey fabrics.

We looked at an outfit she was considering wearing on a date and it was beautiful. She had an easy smile and looked so relaxed in the outfit that it was clear she would attract someone who appreciated her sense of style and the drama that went with it. Why would she choose an outfit that didn’t represent who she was and in which she didn’t feel comfortable?

Then there’s the woman with whom I had dinner recently who said she only wears black and grey. Too much color overwhelms her. In looking at her coloring and her personality it was clear that she definitely would be overpowered by primary colors or the brighter colors that have been so popular lately, but that she could stray from her gray and black and still feel authentic. Beautiful aubergine or a rich merlot, for instance, would look gorgeous on her and would blend beautifully with her black or gray.

Stick to colors that you know look good on you, that make you feel beautiful and that allow people to see you and not just the color.

It is important to keep in mind that your date is there to get to know you. Your outfit should make you shine, but not to the point where it is distracting. Too much jewelry (of course, everyone’s concept of what is too much is different), wearing something tight, short and low all at once is definitely distracting (and, depending on how old you are, it could be age inappropriate) and anything too fussy will take the focus from you, and that’s not what you want.

One of my clients recently went on a date after our shopping trip and she wore something simple and elegant in a gorgeous, flattering color. Her date told her she was even more beautiful in person than in her picture. Wow…that’s what you want to hear!

When you feel comfortable, at-ease in your own skin, and self-confident about what you are wearing, the rest of the date can flow more easily. With no distractions you can focus on getting to know the person you are meeting or really enjoy of those you already know. Smile, relax and enjoy!

For more information about dating, check out Nancy Michael’s book, “Dating Success After 40.” I am a contributor on how to dress for a date.

Please note: All garments pictured here (and in the catalogue) are vegan-friendly (made from fabrics that did not harm any animals).

Some of the affiliate links may generate commissions for Total Image Consultants which helps support the time spent creating these very specific recommendations.

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Jackie: Before
Jackie: After
Diane: Before
Diane: After
Amanda: Before
Amanda: After
Donna: Before
Donna: After
Jan: Before
Jan: After
Sara: Before
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Marianne: Before
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Annie: Before
Annie: After
Meryl: Before
Meryl: After

When you begin to dress like yourself you can’t live any part of your life NOT like yourself. Working with your inner beauty words is very powerful and contributes to many positive changes beyond your wardrobe. Jennifer, Germany