"きのうはこの赤いネクタイをしめました。"

Translation: I put on this red tie yesterday.

[NessDan]

"I put this red tie on yesterday" should be accepted I feel

[Eldozarino]

'Put on' sounds like i put it on yesterday and havent stopped wearing it since then. 'I wore' would be a more natural translation

[AnthonySan012]

I do agree "I wore" sounds a lot more natural, but the sentence uses しめ for closing/tieing/putting on the tie.
If you want to be literal and say "I wore the tie," you'd have to say ネクタイをきてました.

[testmoogle]

I'm not sure きていました (着る) is really ever used with ネクタイ...

It should be しめていた (締める), or you can use していた (する).

ネクタイを締めていた。
ネクタイをしていた。

In fact, if you do a Google search for the sentence you wrote, it only finds one page on the whole internet -- which is this very Duolingo discussion page!

• "ネクタイをきてました" = (1 result)
• "ネクタイを着てました" = 0 results
• "ネクタイをきていました" = 0 results
• "ネクタイを着ていました" = 0 results
• "ネクタイをきていた" = 0 results
• "ネクタイを着ていた" = 21 results*
• "ネクタイをきてた" = 0 results
• "ネクタイを着てた" = 1 result*

* Of these 22 results, nearly all of them are talking about multiple items of clothing (e.g. シャツとネクタイを着ていた). All of the other three or four results were written on the same website by the same person (specifically about wearing a bow tie, "蝶ネクタイを着ていた", rather than just ネクタイ).

• "ネクタイを締めていた" = 10,500 results

[JohannesRu793051]

The 2nd meaning for 締める (しめる) on jisho,org is "to wear". Also when you use the Duolingo tooltips "wore" is one suggestion. I reported that "wore" should also be accepted.

[MaynardHogg]

締め出す作戦？
Why can't this verb join all the other "wear" verbs? 被る, 着る, 填める, 履く…

[Medusa747]

And that's why we can't wear that tie today.

[hiba226886]

きのうはこの赤いバターを掛けました

[daniel.z.tg]

昨日　　は　この　赤い　　ネクタイ　を　締　め　ました。

きのう　は　この　あかい　ねくたい　を　し　め　ました。

kinou　wa　kono　akai　nekutai　wo　shi　me　mashita.

yesterday　(subject)　this　red　tie　(object)　to_tie　(transitive)　(past tense)

Yesterday, this red tie, I tied.

[vivalaashutosh]

Yesterday I put this red tie on wasn't accepted

[Seattle_Scott]

We wear ties. A tie is worn, not put on. If I put on a tie, after that I’m wearing it. Who comes up with the English for the Japanese? This is like English written by the 文部省 for high school students.

[Rafa279213]

Wore should be good

[cgottsch]

ooo what did she say bro

[Tom240]

Don't you use する for putting a tie on?

[MaynardHogg]

I frequently do.

[Alex828675]

"What a story, Mark"

[RailGuit]

I SPECIFILY TOLD YOU NOT TO WEAR THAT RED TIE FOR GODS SAKE

[AlonzoAntoku]

why is "used this tie" not the same as "put on this tie" or "wore this tie". Its the same thing.

[MaynardHogg]

The Spanish course drilled me in usar for clothing, but English only uses that verb for non-wearing (wink) uses.

[HarbingerOfMilk]

what an exciting life you have

[MaynardHogg]

I wore this necktie yesterday.