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Answer for the clue "Son caught Trump meeting single lady on vacation, in a shabby fashion ", 9 letters:
scruffily

Word definitions for scruffily in dictionaries

Wiktionary Word definitions in Wiktionary
adv. In a scruffy way.

Usage examples of scruffily.

Tall, narrow-hipped, wide-shouldered, quick of movement, t4egant yet somewhat scruffily dressed.

Mal thought uncomfortably that she was overdressed in her cashmere, while Jordan looked scruffily at home in his faded jeans and the beat-up jacket.