The breakfast event it just a character intro to have the bobby to wonder what "Lucy" is doing, it wasn't needed before 15.44 (you could have skipped this) just like you can still buy everything from the store and break other events and dialogue options before you are asked to go get said items.
The issue I (personally) believe that some event, action or dialogue breaks the dress event. if you do not immediately give her the dress on the upcoming "Wednesday evening" in the "living-sittiing room" after the dialogue of her "Lucy" having nothing to wear.
Example: if you get the dialogue trigger on the "Friday" you must give "Lucy" the dress on the following "Wednesday evening".
Best case scenario is to start a new game latest version (atow v15.48) save before any interaction with "Lucy" until the dialogue "of her wanting a new dress", buy dress from store, give dress to her as soon as possible. if it doesn't trigger give the dress to her on "Wednesday evening" reload the save of before the dialog of the request, reload that same save until it does say give "Lucy" a new dress on "Wednesday evening" in the "living-stiitng room".
Best working practice is to trigger the dialogue of "wanting the dress" on "Monday" buy the dress on "Tuesday afternoon" to give "Lucy" the dress on that "Wednesday evening".
This limits the possible interactions with other characters the may have detrimental effects via dialogues, events or actions on the "dress event".
If you miss the first "Wednesday evening" after dialogue of "dress request" there is a 75-80% of the time, breaks it.
If you purchase the dress from the store before "Lucy" "dress request" dialogue, breaks it.
If you migrated from an older version depending what actions you took in the older version, may break it.
Anything beyond the extremely limited parameters above, may break it.
This is "dress event" is bugged as far as I am concerned it is not easily completed.
Out of the 30 or so play through's; I have only completed this maybe 5-7 times, of these all have been new games (various version).
No once has a migrated save from an older version has worked (if it has for you then tell me what you did

).