What to Wear to Be Ready For What?

I’m a townie to the core which means once I drive somewhere that I consider far away, then pretty much in my frame of reference, I am not thinking of terms of going back in the same direction, which is just a presumption.

But when you think about it, getting in the car and going back in the same direction will feel like the first time to the person you were driving to?

Anyway, when I am driving to an area of our small island that I am not overly familiar with,thing is I don’t know how to dress ‘local’ for that locale.

Add to that, I don’t really know what to expect in how my date is going to dress.

Add to that, I don’t know what we plan to do.

But I like to go with the flow.

Barring packing a whole suitcase of choices, I try to downsize what I bring so I don’t look like I’m bringing too much.

How much is too much?

What am I really saying in the language of the new relationship?

I think I am trying to say, I don’t want to look assuming so I am trying to look unassuming, so thus, I bring less than what I think I need.

One time, I went with my girlfriend to SF for 3-4 days.  I always admired her because she would bring clothes that all worked together and accented her outfits with silk scarves.  I always packed a bunch of clothes for whatever mood I was in, so I usually ended up wearing something towards the end of the trip which I really didn’t think was appropriate but nevertheless was what was clean.  (As an aside, the last morning we were there that trip, she was wearing her pajama t-shirt with a silk scarf, and still managed to look chic).


I’m challenged in what can I bring that is casual yet elegant?  I’m not big on wearing a lot of big jewelry so those articles on dressing up your outfit with necklaces and such fall flat for me.  I’m also not a pattern person. I’m a simple dresser, the less I have to deal with the happier I am.

Another traveling story.  I had gotten packing lightly down to the point where, if I was going to my Mom’s I’d be washing what I brought, and sometimes wearing a t-shirt my sister left (which would really piss her off if she knew).

Yet another digression.  Where I expanded my horizons and I really started packing more than I would ever need (which would secretly bug me).  I travelled with people who brought waaaaaayyyyyy more than would ever be used.  For a neighbor island trip, they would bring a full size suitcase and a duffle bag of shoes and other stuff.  I got used to that and started doing the same, bringing a full size case for a few days.

Nowadays, I’d rather just be unencumbered.

You know, take the baggage free option.

I got that right.



I am planning to bring a long black, tube dress strapless that I can wear with my platform slippers, make my hair bigger or smaller, that feels about the right speed. I could wear this on a Sunday day.

But I’m bringing the option of white jeans, sandals that will go with either outfit, and maybe a black or sparkly top.