
Be left with nothing but the clothes on one's back
Be left with the clothes you are wearing / Be taken to the cleaners / Lose one's shirt / Take someone to the cleaners

Restare in braghe di tela 
Restare in mutande / Restare senza il becco di un quattrino
Be left with the clothes you are wearing / Be taken to the cleaners / Lose one's shirt / Take someone to the cleaners

Restare in braghe di tela 
Restare in mutande / Restare senza il becco di un quattrino
Examples
I invited my future in-laws to a gourmet restaurant. I made an excellent impression, but the meal was outrageously expensive and I was taken to the cleaners
Ho portato i miei futuri suoceri in un ristorante tre stelle. Ho fatto una bellissima figura, ma il conto era salatissimo e sono rimasto in braghe di tela
Thomas was a compulsive gambler and used to gamble huge amounts of money, until he lost everything and he was left with only the clothes on his back
Tommaso era un giocatore incallito e ha sempre giocato cifre enormi, finché non ha perso tutto ed è rimasto senza il becco di un quattrino
It's a good thing that my friend decided not to sue that big company, because he was wrong and he would have been left with just the clothes on his back
Meno male che il mio amico ha deciso di non fare causa a quella grossa compagnia, perché aveva torto e sarebbe rimasto in mutande