I haven’t been on a date date in a very long time. So I have no recent first hand experience with dating and date-appropriate outfits. Of course, Greg and I do have date night and in that case I’ll wear something that he especially likes, which means NO ruffles or extra shiny fabrications.
I do have a lot of recent second hand experience with dating outfits though. I have many single clients, at many different stages of life, that request my help with date-appropriate attire. We often end up building “a date wear capsule”, which also includes daywear options because a date can mean a mid morning cup of coffee, an early afternoon stroll, or a ball game.
I suggest to my clients that above all else, they should choose a dating outfit that makes them feel comfortable and confident. For some this means jeans, blouse and boots. For others it means a casual dress, denim jacket or cardigan. Or it can mean a skirt and top, trousers and sweater, jacket and short shorts, or sheath and heels.
Being comfortable also has to do with how you relate to your context. In other words, your outfit should be appropriate for the occasion on the casual/formal scale. You might not be comfortable wearing a cocktail dress when everyone else is in jeans, and vice versa.
So the basics are all about you being relaxed in your outfit: How you feel wearing it and how it fits the occasion. Seems simple enough. But my experience with clients tells me this is easier said than done. There are two deeper questions that almost always come up.
The first question is around the extent to which you are going to reflect your normal fashion persona. Personally, I fall into the “just be yourself” camp. If you are a dramatic, trendy and flamboyant dresser, this should come through in your date wear. If you are a modest, preppy and classic dresser, show off these great looks. Dress romantically if that tickles your fancy. If arty and edgy ensembles are your thing, don’t hide them. It’s best that your date sees the way you normally dress straight off the bat.
Of course, there are also good arguments for playing it safe on date night, tempering your style to avoid preconceived judgements. Perhaps you will stick to neutral colours instead of your normal brights, or forgo the clanking and jiggling jewelry that you normally wear. Maybe you’ll go without your favourite perfume in case your date has allergies. Maybe you’ll wear contact lenses instead of your specs.
The second tricky question concerns the alluring factor. Should you show more skin at date time? Should you wear something form fitting? My advice on this one is, again, to be yourself. If you are a naturally modest dresser, don’t feel the pressure to wear something more tight or revealing. If you feel good showing some more curve and skin, go for it. Keeping in mind the dress code of course.
These are the main questions that I thrash out with my clients. Some want to pull out all the stops and look as alluring and dramatic as possible at date time. Others feel they should reign in their eclectic style and play it safe. There are no right answers that apply universally to all women — ultimately the right thing for you will be the decision that makes you the most comfortable and confident. Then you can relax and have fun.
I would love to hear your point of view on how to dress for a date. Whether you are currently on the dating circuit of not, what are your suggestions for date-appropriate attire?
