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Especially with names I have often seen this romanization, but also with other words. Here is an example where the word 우리 is transliterated as "woori". Other examples are the Korean bank "Woori Bank" (Wikipedia) or the korean first name Hyun-woo (현우) with its common english spelling.

Why is the "w" at the beginning being used, instead of just "oo"? I would expect "Oori" to come closest in terms of pronunciation when transliterating 우리 to English. Is the correct pronunciation of 우 actually closer to "woo"?

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I deem that you already know the correct romanization is u when you follow the official Korean language romanization system. I would say that there are several reasons for using woo instead of oo and u, but others might disagree at some points:

  1. A lot of people want to conform to the custom. It is an idiomatic transliteration going against the official (standard) rules. Even 노태우, a former president, has used Roh Tae-woo. You should also note that some people use wu, u, oo, wooh, etc. no matter what others use.

  2. 양병선 stated that woo (/wuː/) should be used for 우 (/u/ or /uː/). He considered that there are very few English monosyllables starting with oo or u. For oo, indeed, I can find only a few: oof (/uːf/), oops (/ʊps/), ooh (/uː/), and oomph (/ʊmf/). Furthermore, English dictionaries that I usually consult have woo but not oo. Thus, the spelling woo should look more familiar and natural than oo (In my opinion, "Woo" looks much better than "Oo"). Although the pronunciation, /wuː/, is slightly different from 우, Koreans can still take it as 우 since no other Korean vowels sound very similar to or the same as /wuː/.

  3. When woo represents the last Hangul character of a name, it shows that the character is 우 not others. For example, 건우 can be written as Gunwoo or Gunoo; in this case, woo clearly shows that 우 is included in the name while Gunoo represents either 건우 or 거누.

  4. When a vowel comes before oo, it could be difficult to find the syllable boundaries. As far as I know, using the hyphen is not always allowed. If you write 태우 as Taeoo (not as Taewoo), it is likely to be mispronounced since a, ae, eo, and o represent 아 (ㅏ), 애 (ㅐ), 어 (ㅓ), and 오 (ㅗ), respectively. Of course, there are no Korean names like 타어오, but a lot of English speakers will not know it.

  5. When it is difficult to differentiate between Korean and Japanese names, oo might be pronounced as /oː/ because Japanese people romanize ō as oh, oo, or ou for their passports. In another similar situation, using u might be a problem because Japanese u (う) sounds different from Korean u (우); like a consonant, a vowel is a phoneme. The pronunciation of Japanese u is one between 으 and 우.

  6. If one has 우 as her/his family name and her/his family member (usually, her/his father or her/his sibling) has already got a passport with 우 romanized as Woo, she/he needs to use Woo as her/his romanized family name to obtain her/his passport. This is mandatory.

  7. If 우 is either your first name or your last name, a single-letter romanization like u can cause trouble as this suggests. For example, a lot of English websites disallow single-character names.

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  • With respect to the first point, I think it's possible the character 노 has it's roots in a Chinese character that can be written as Roh (similar to how old names with 이 used to be written as Rhee, eg 이승만). Also the North Korean state news paper is named 로동 신문, which I believe is their version of 노동. 우 being written as Woo might have similar roots.
    – user17915
    Commented Sep 15, 2020 at 8:40

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