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How to simplify a sentence so that a younger audience can understand it?

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I have the following sentence:

Pocket squares are a standout amongst the most vital apparatuses for a man of style. It's important to have the correct pocket square for the correct event.

I feel the first sentence is a bit too advanced for the average reader. I am trying to see how to scale it down so that a 13-year-old boy could comprehend the sentence.

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You can't. 13 year old boys don't care about pocket squares. Period. End of story.

There is a vast overemphasis in the writing community on how things are written. The emphasis should be on what things are written. Most communication project do not fail because of how things are said but because of what things are said.

The core of the writer's craft is to figure out what the reader is interested in reading about. Figuring out the best way to say that thing to the reader is important too, but it is icing on the cake. The reader will plow through less than perfect prose to get to a subject they care about. But there is no perfection of prose that will make the reader care about a subject they don't care about.

The question you should be asking, therefore, is "How can I make a 13 year old boy care about pocket squares." The answer is probably that there is no way on God's green Earth to make a 13 year old boy care about pocket squares. But if there is one, it is saying something different that will catch their attention, not dumbing down the prose to make the sentences simpler.

A really great writer might make a 13 year old care about pocket squares, but it would be by what they said about them, not how they said it.

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How rephrase the following sentence so that it can be understood by a 13-year-old boy?

Pocket squares are a standout amongst the most vital apparatuses for a man of style. It's important to have the correct pocket square for the correct event.

Word frequencies

To simplify the sentence a good method would be removing or replacing the words that are more difficult for younger readers.

You could use the SUBTLEX-UK corpus. It is slightly more accurate in predicting word recognition than other corpora such as the British National Corpus, CELEX, and the Google corpus. More importantly, it includes columns with word frequencies derived from subtitles of television programs for preschool (i.e. CBeebies), and primary school children (i.e. CBBC). A Zipf-scale gives a natural frequency ranking from 1 (low frequency) to 7 (high frequency). For example, the word elephant has a CBeebies Zipf-value of 5.23 and a CBBC Zipf-value of 4.76. You could look for words with a Zipf-value below 3 and replace them. Though you should use your intuition about which words might cause difficulty.

Additionally, you could use Children's Printed Word Database (CPWD, 2013) which has word frequency data derived from books for 5 to 9-yo children. The words in this database should be safe to use for 13-yo readers.

For the word pocket square you could check the SUBTLEX-UK-bigrams. If the reader does not possess L1 comprehension, but learns English as a second language, the concept pocket square could be difficult. They would either need use a dictionary, or you could give the meaning yourself. From Wiktionary:

A handkerchief used as an accessory to a suit.

Illustrations

You could use a picture to illustrate what the concept means.

wikipedia pocket square

Search and Destroy

Pocket square might be a difficult concept for L2 English learners. Give a description of what it is:

A pocket square is a folded handkerchief in the breast pocket of a suit, used as an accessory.

The word standout can be found in the SUBTLEX-UK and has a Cbeebies (preschool) Zipf-value of 2.23 and a CBBC (primary school) Zipf-value of 2.47. They are both scores below 3, so better remove this word or replace it with a synonym. The word exceptional has better Zipf-values of 2.71 and 3.72.

The word vital has Zipf-values of 2.71 and 4.48. The word apparatus has Zipf-values of 2.53 and 3.43. Some readers might have difficulty with these words. You could rephrase by saying 'in order to become' or 'to be'.

A pocket square is a folded handkerchief in the breast pocket of a suit. It is an exceptionally vital accessory to be a stylish man. It's important to wear the correct pocket square for each event.

To summarize, in order to rephrase sentences so that 13-yo readers will understand them you could explain difficult concepts. And you could replace possibly difficult to understand words by more frequent used words that can be classified by children from age 5 to 12.

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What sticks out to me about this sentence is not that the descriptor "apparatus" for a pocket square is too difficult, but that it is simply wrong. An apparatus implies a complex assemblage of parts, whereas a pocket square couldn't be simpler.

This suggests to me that the underlying problem may be that you are trying too hard to affect a sophisticated tone in your writing. I can attest, from personal experience, that nothing falls flatter than making a mistake when you're trying to show off your vocabulary. Concentrate instead on saying what you mean directly, and everything else should take care of itself. For any words you use that you think your audience might not be familiar with, just explain them right there in place (that's what Shakespeare did). I use this technique often, since I also enjoy using unusual or original words, and it not only helps the reader, it also serves as a check to make sure I really do know what the word means before using it.

A pocket square (a fancy, decorative handkerchief used mainly for show, and displayed in your pocket) is a standout part of a stylish man's outfit. Make sure you choose the right pocket square for the right event.

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