Yesterday one of my friends texted in our ever going group chat:

Friend: OMG Just got asked to speak at a national conference in x.

Me: Congrats! So awesome! Love that city! What an honor! What are you going to wear?

So no matter what I say or do, it really all comes down to “What am I going to wear.”

Ann said the same thing yesterday. She stated that she now knows who she is, knows what makes her comfortable, but there are times when you inevitably ask that question…Yes- most of us have reached the age where we have our look or our uniform. We have stores we frequent and styles we prefer. We know who we are and are confident enough to own it.


There are still moments when we look at our date book, look in our closets, and just go “Hmmmm”

I have my evening event look, and I have my day event look. That’s easy. I don’t even think about what to wear to a wedding or funeral. But what about those curve balls? My tea society is having a summer event in June- the invite says dress or suit please. OK. I can do that. But then it says “Hats optional.”

Hats optional?

And I don’t mean baseball caps. I know what kind of Kentucky Derby, Sunday church hat that is being spoken of. So do I buy a hat for the occasion? Or do I sit there and be the only person not wearing a hat? It really doesn’t matter: I don’t think anyone is going to .point at me and hiss “Traitor!” But should I wear a hat?

Where do I even buy a hat?

The colleges that my daughter has been accepted to have meet and greets. This was a troubling one for me. Do I go business like, or is that too much? How casual is casual? What’s the proper middle of the road look? (For the record, I went with black dress, grey long cardigan and black flats) Yes, I was far too worried about what the other parents would think of me.

What it comes down to for me is that I want to be myself, so I stick to my neutral palette. Fine. But I neither want to stick out, nor blend in the crowd. I want to have my own individual stamp, but I don’t want everyone staring at me when I enter a room. Unless of course I’m winning an award and then stare all you like. Sort of like a non conforming conformist…

Yeah.  I know. That doesn’t really make sense. But do you kind of know what I mean?

I wonder if I’ll ever be completely at ease as far as wardrobe is concerned. I’m in capris and a t shirt right now and I am content and comfortable. It is the perfect outfit for writing and errands. And 98% of the time I am totally confident in my look. But that other 2%? I just think there will always be that little sliver of time when I have that little sliver of doubt. I think that 98% of the time I dress for myself and myself alone: but that little tiny 2%? I think that I’m dressing for someone else. And whenever you are doing something for an audience you have that certain hesitation- You second guess yourself. You wonder if you should take a risk, or if you should play it safe. What will X think of me if I wear this outfit? Will they think I’m beautiful, sexy, smart, powerful? Or will they think I’m trying to hard? Or not trying hard enough?

In the end, I think I will always be plagued by those four little words “What should I wear?”




41 thoughts on “What Should I Wear?

  1. Ah, well, let’s throw in another parameter: where is the event going to take place? Different regions within the US have differing definitions of casual, formal etc (except I think all places understand when it is stated ‘black tie’).
    Coming from the western US, our idea of dressy is very different from those from your part of the country, especially the inner niche of NYC. So, if I were to attend an event in NYC I would definitely take that ‘parameter’ into consideration in forming an outfit still in keeping with my own ‘western’ aesthetics…aka being myself (and I’m not talking about wearing cowboy boots are anything like that stereotype).
    Actually, my fallback when in doubt are my selection of performance clothes…when in a pinch, they have served me well both on-stage and off!

    Liked by 3 people

    1. I know! Different areas of the country have different versions of what’s “right”. Oddly I’m going to talk about that tomorrow. One of my friends has an out of town wedding….the drama she is going through figuring out an outfit!! I usually change up shoes and jewelry but wear the same dress, but yeah….good times!

      Liked by 1 person

  2. We all have that issue. I have been known to change 3 times until I feel right, depending on the event. Usually by the third tweak of the outfit, I am good. I guess 3’s my magic number. LOL So did you get a hat???

    Liked by 2 people

      1. Oh no, my husband goes through his closet like a madman when we have to do something different. Has to try on multiple shirts, suits and pants to see if they fit, what goes with what picks out a ties or should I say I pick out a tie.

        Liked by 1 person

  3. This is very easy for us… If it is ultra formal, it would be a sari. If it is semi formal, it would be a traditional Indian wear which has a bit of jazz on it. If it is informal then it would depend on the occasion – a party would be jeans and a good top (not a t-shirt). I wear according to my comfort and season as it is extremely hot here so satin and crepe won’t work now. I am mostly in Indian outfit or a combination of jeans and an Indian top

    Liked by 2 people

  4. I just got a hat recently! I love them but most of them are too big. Guess I have a small head. Finally found one that has an adjustable band so I can make it fit. Bonus, my husband loves it. I think it reminds him of a time when we were dating and I wore a hat to pick him up at the airport when he was coming home from a trip. Those were the days you could go to the gate. Also found one with a huge brim that is the spitting image of the one in my Bitmoji. The kids want me to get that one. LOL

    Liked by 1 person

  5. I guess I may be in the minority, but the last thing I think about is what am I going to wear. There are so many factors including weather. I was in sandals on Tuesday and snow boots yesterday. My feeling about the what to wear question – wear something that is comfortable and the beauty will shine from the inside out!

    Liked by 2 people

  6. I had a giggle. A couple of years ago while visiting Churchill Downs- I bought myself quite the large- fancy hat. My husband was not impressed because of the price and said ‘What do you need this for?’ and I told him ‘Every girl needs a fancy hat… just in case!’ I love my hat… it is a conversation piece when friends come over they ask to try it on! LOL

    Liked by 1 person

  7. Well, I suppose sometimes you want to dress up. I’m mainly past that. That might sound so boring, but I got sick of outfits, worn once, to a wedding, say, in the back of the wardrobe forever more. I have ‘my clothes’ – I’m comfortable in them, and they are wearable for just about every occasion, including funerals. I rarely wear black – even for funerals – but that is a personal thing.

    Liked by 1 person

  8. Good luck with the hat shopping. I love hats, but admit it’s hard to find a nice one since so few people wear them anymore other than as winter wear. A nice garden party hat would be lovely.

    Liked by 1 person

  9. If it’s any comfort to you, you’re not alone. “What am I going to wear?” is a question that plagues so many of us. We want to dress for ourselves, and to an extent, we do. But we also don’t want to give offense by being inappropriately dressed, or to call unwanted attention to ourselves (by being inappropriately dressed) or uncomfortable (by being inappropriately dressed). Do you see a pattern here? LOL! Sometimes, coming up with an outfit that is comfortable to wear and also makes us comfortable in our surroundings is difficult!


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