Word: 

Words and phrases that rhyme with dressiest:  (1 result)
3 syllables:
messiest
Words and phrases that almost rhyme †:  (12 results)
2 syllables:
sentient
3 syllables:
cheviot, nescient, deadliest, elliot, elliott, heaviest, wealthiest
4 syllables:
inebriant, consentient, dissentient, prevenient
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— Nouns for dressiest: solomon, clothes, person, occasions, uniforms, hen
— People also search for: chicer, mandarin collar, dolman sleeve, safari jacket, fashionable, seasonless, glen plaid, monokini, stonewashed, culotte, overdecorated, more...
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