What to Wear When You Don’t Know What to Wear

I sometimes find “casual” dress more confounding than “formal” — particularly when I am told to dress casually for an event that has some formal associations like a holiday dinner, a fundraiser, or anything involving a religious officiant.

Working on the theory that it’s always better to be overdressed than underdressed, here is my no-fail formula for such occasions when your host tells you that you can wear jeans but your heart tells you that you can’t.
Wear a nice sweater and knit trousers. Or, a nice sweater and interesting canvas pants.
Nice sweater

I am the Edward Gibbon of sweaters
What is a “nice sweater”? It’s sort of like a Sweater of Substance — which was the subject of lengthy exposition in late 2017 and early 2018. If you missed those posts, there is no time like today to catch up: Part I, Part II, and Part III.
Good grief! I wrote four posts on this subject: Part IV.

You will also need an interesting bag.
Boom! You have an interesting bag now

You’ve seen this sweater before, but not like this.
That is a huge fib. It looked a lot like this first time around. But I have added a narrow belt, which I think adds a little chic.
Huge fib = lie

Elegant but distinctive; thinking deeply about fibs and lies
I like this sweater even more now than I did when I bought it. It’s turned out to be very useful.
I also like it better with the belt than without.

There is a small chance that I could be mistaken for a religious officiant in this sweater.
Church of the Holy Sweater

Bonus: More Philo. Please ignore the detritus on the ground. We are not slobs.* You are seeing a combination of his toys and things we moved out of the way while taking photos in the dining room.
Sweater: J.W. Anderson from YOOX; Pants: Ann Taylor; Shoes: Taryn Rose; Bag: Sophie Hulme Bolt bag
How has Philo already mastered the long-suffering look? Is Harper coaching him from the beyond?

* That is a small fib.

7 thoughts on “What to Wear When You Don’t Know What to Wear”

  1. I also find casual dress far more difficult than formal. Even if jeans are appropriate for most events in my life, I struggle with footwear choices, and I just prefer skirts.

    Last week I was going down a rabbit-hole of your past posts, and I saw the recommendation for “Gaudy Night.” I’ve never read Dorothy Sayers, but I needed a new novel for holiday travel, and I love period British mysteries. The book was amazing. Not just the mystery part, but the characters and their social commentary and how it all intricately fit together. Wow. Thank you, I will be reading a lot more of Ms. Sayers’ work.

    • I love Dorothy L. Sayers. That is one of the best for social commentary, but most of them have many layers. THE NINE TAILORS is perfect for New Year’s Eve.

  2. This is the perfect compromise between the head and the heart of a casual occasion. I adore the sweater. It has presence and self-respect, while winking vigorously to the room at its historical nods. And it’s proportions are excellent.

    In California, we often bridge the “jeans are acceptable” line with jean-cut pants not in blue or black denim. This Thanksgiving, I wore black velvet jeans with leopard print boots, a chiffon tiger print blouse in the same animal pallet over a black camisole. And either a dressier brown jacket with a very subtle snakeskin print at the Big Meal, or a black v-neck cardigan for dessert and games (it was a movable feast). The velvet jeans worked a treat.

  3. I feel like the public needs to dress up more when possible.

    I feel somewhat mortified when I attend a concert at my children’s school and I see adults in the audience wearing sweatpants and sporting wear. Unless there is an epidemic of illness, or they are poverty stricken, but that is not the case… The students are all in dressy attire, wearing the requisite black up on stage… why don’t the adults dress up? End of rant.

    Yours is an example of a perfectly acceptable outfit for many occasions. Including a middle school orchestra concert…


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