I was asked the other day “What should I wear on a date?”

Ah… I don’t know.

But I’ll help you work it out.

We’ve all been told the importance of first impressions and usually, we want a date to go well, otherwise, we’d stay home and watch Netflix. 

I’m also going to assume you want to look good. 

In my experience, if whoever is organizing the date is thoughtful and someone you want to know better, they provide helpful information. The savvy ones send you a link to the restaurant/event so that you can plan accordingly.

Unless they cheerfully tell you “It’s a surprise!” which is bloody annoying. How am I supposed to know to wear rain boots/ski gear/an evening gown/latex if you don’t give me a hint? 

So, assuming you know who you’re going with, where you’re going and when (and if you don’t make sure someone can track your cell phone or identify any distinguishing marks), focus on three things. 

Genuine
Courtesy
Comfort. 

Genuine:

I’ve never found the advice “be yourself,” particularly helpful –  who I am changes based on my mood or what I’ve read in Oprah. Here’s what I mean by genuine. Check in with your feelings, beliefs, values and goals and dress accordingly. If you’re an introvert, this is not the time to wear your best friend’s red leather mini. If you love outrageous clothes, don’t listen to anyone who tells you to dress like a nun. You have been invited out because of who you are, right here, right now. And you’re awesome. 

Courtesy:

Remember I said dress genuinely? You can still be courteous. Unless the party is being held for you, or you’re about to accept an Oscar, you may want to temper your choices while still dressing authentically. One lovely young woman I know keeps the female pronoun, is lesbian and dresses in male clothing. Because it was important to her sister, and she was a bridesmaid, she wore an elegant pantsuit to her sister’s wedding that was  more feminine than she usually wears and grew her hair out so that pretty decorations could be added. Was she being true to herself? Yes! She adores her sister and knew the day wasn’t about her. Taylor is accepted and seen for who she is, she wasn’t hiding or being dishonest, it was simply a gesture of thoughtfulness and love. If you can’t do that, skip the event or the date, you weren’t meant to be there in the first place. 

Also under courteous – if you’re going to be on a boat with wooden floors, don’t wear stilettos. If you’ve borrowed a friend’s expensive dress (which I don’t recommend, hire one instead) get it dry cleaned before returning it. 

Comfort aka practicality:

Wear what won’t get in the way of you having a good time – and being a good sport. Don’t wear high heels if it’s been raining and you’ll be on grass. If it’s a picnic, add insect repellent to your ensemble (preferably a pleasant smelling one). If you can walk in heels for miles, then go for it, if you can’t, hobbling after twenty minutes can kill a mood, especially if your date has forgotten where they parked the car. I’ve got clients who carry lightweight slip on comfy shoes in their bags to change into once out of sight. Great if you’ve been dancing all night. 

If you’ve never worn an outfit before, try a test run. Also, have a back up outfit in case you put your first choice on and the @%#!! skirt no longer does up/you can’t find the right bra/it starts to rain and you don’t want to ruin your suede boots. 

If you want to look sexy on a date, wear whatever makes you feel that way, not what others tell you (keep in mind that ridiculous or not, extremely low cut tops or going bra less can be distracting, I’ve seen them cause waiters to spill soup). And if your Spanx are too tight, you’ll struggle in the loo. Trust me, I know.

Try to layer – carrying a bulky coat can be awkward, not all places have coat check but shivering isn’t fun either. I often take a wrap that fits easily in my bag. If your date is a decent human they’ll feel obliged to do something about it while secretly wondering why you don’t know how to dress yourself. You want to enjoy the ambiance, your companion and the environment – your clothing should enable that, not hinder it.

Still not sure? Call me. We can talk it through together. 

PS. it’s more important to find out what you think of them, than what they think of you. 

Have fun!

Aroha, 
Erin
Wear Happy!