What to Wear on a Date

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what to wear on a date, what to wear valentines day

So what do you wear on a date? It can be a particularly vexing question for many women, particularly if it’s with someone new or newish. We don’t want to get it wrong – either seem too forward or too uninterested. Given that it’s Valentines day in a few days, I thought I’d give you some guidelines to help you make a decision about what you should wear on a date, because I can tell you, that it’s about you, not a generic outfit!

What do you mean Imogen that you can’t just tell me what to wear? I hear you ask your computer screen?

Well I can’t, because, it’s about the whole you and what you want to communicate.

So how do you decide what to wear? Well let’s take it back to the concepts of Yin and Yang and choosing the clothes that suit your personality and express who you are (not some imagined version that you think he will like but is not you, it’s best to always be authentic in a relationship).

Yin elements make you appear softer, more approachable, more nurturing and warm.
Yang elements make you appear stronger, more powerful, more demanding and less open.

So when thinking about what you wear on a date, you will want a combination of these both, nobody wants to be a pushover. But you will most likely wear more Yin elements as being approachable, friendly and warm are good traits when dating!

Yin elements include details such as softer fabrics (touchable even), curved patterns and lines, smaller prints, lower contrast and lighter colours (umm, yes that LBD is making you look unapproachable).

Yang elements include stiffer fabrics, darker colours, higher contrast and bolder patterns and lines.

So how do you choose what to wear from your wardrobe for a date? Think about who you are and what you love, start there and then add in what you want to communicate. Do you want to be mysterious? Do you want to seem fun?

Now how about sexy? Well sexy and alluring are great, but is this a first date or a date with your husband? Sexy with your husband or partner is brilliant, sexy with a first date may be giving off too many of the wrong vibes. As one of my male friends once said to me “I like my presents wrapped”. Leave something to the imagination!

What to wear on a date - subdued sexy


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  • I’ve a question about Yin and Yang but about a different occasion. (which is a topic I love when understanding the elements of a style. Its easier to understand than the genereric styles classic, preppy, romantic, elegant etc.).
    You often mention that bright and high contrast colors tends too look more authorative (or serious-like) than the more muted and lighter colors. But everytime I read about these colors, especially red and orange, people always complain they are too playful or too sexy for more serious/conservative settings.
    but on the contrary, pastels are often come off as too “girl”-ish or young too many people, so I found Yin and Yang a bit confusing.

    They seems to contradict with the typical communication when it comes to red and orange – like doesnt black with bright red or bright orange come off (or rather stereotyped) as too “sexy” or too agressive in more conservative settings rather than serious?

    I’ve two pencil skirts, one in true red and one in a pastel mint-green. Which one is actually better when you want to be taken seriously in more formal or conservative occasions?

    • HIgh contrast looks more authoritative, and a bright colour with black can also look like that, but otherwise muted colours also can carry authority – when they are darker (which is more yang) but not lighter (more yin). Always there is context to consider. But a man may wear a red tie in a conservative environment and nobody thinks he’s trying to be sexy!

    • And as far as the pencil skirts go – red is more dramatic and bold, while mint green is more conservative, but also more feminine – so if you want to be taken more seriously in a conservative or formal occassion wear a neutral instead.

      • Well, I know that neutrals are always better, but I just was wondering which one was better of those particulare colors, because often they often contradict in most context colors tends to be more “casual”, so thats why I found a bit confusing (like how can brights be ‘yang’ when they are basically hated to many occasion.) Red is one of my favorite colors and a signature, yet its one of those colors that are hated in most contexts, but thia seems to be a cultural thing because colors doesnt matter where I live, but I know many people who are from other countries, so Im just trying to understand the logic behind it. ^^;;

        …..errrr., I guess Im overthinking it. 😛

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