Of American-English origin, the phrase like the wreck of the Hesperus means in a sad state, or, merely, dishevelled.
This phrase refers to The Wreck of the Hesperus (1840), by the U.S. poet Henry Wadsworth Longfellow (1807-1882)—this is the poem, as published in The Pittsfield Sun (Pittsfield, Massachusetts) of Thursday 30th January 1840 (Norman’s Woe is the name of a rocky headland, reef, and islet on the coast of Massachusetts, between Gloucester and Magnolia.):
It was the schooner Hesperus,
That sailed the wintry sea;
And the Skipper had ta’en his little daughter,
To bear him company.
Blue were her eyes as the fairy-flax,
Her cheeks like the dawn of day,
And her bosom sweet as the hawthorn buds,
That ope in the month of May.
The Skipper he stood beside the helm,
With his pipe in his mouth,
And watch’d how the veering flaw did blow
The smoke now West, now South.
Then up and spake an old Sailor,
Had sail’d to the Spanish Main,
I pray thee, put into yonder port,
For I fear a hurricane.
Last night, the moon had a golden ring,
And to-night no moon we see!
The Skipper, he blew a whiff from his pipe,
And a scornful laugh laugh’d he.
Colder and louder blew the wind,
A gale from the North-east;
The snow fell hissing in the brine,
And the billows froth’d like yeast.
Down came the storm, and smote amain,
The vessel in its strength;
She shudder’d and paused, like a frighted steed,
Then leap’d her cable’s length.
Come hither! come hither! my little daughter,
And do not tremble so;
For I can weather the roughest gale,
That ever wind did blow.
He wrapp’d her warm in his seaman’s coat
Against the stinging blast;
He cut a rope from a broken spar,
And bound her to the mast.
O father! I hear the church-bells ring,
O say, what may it be?
’Tis a fog-bell on a rock-bound coast!
And he steer’d for the open sea.
O father! I hear the sound of guns,
O say, what may it be?
Some ship in distress, that cannot live
In such an angry sea!
O father! I see a gleaming light,
O say, what may it be?
But the father answer’d never a word,
A frozen corpse was he.
Lash’d to the helm, all stiff and stark,
With his face turned to the skies,
The lantern gleam’d thro’ the gleaming snow
On his fixed and glassy eyes.
Then the maiden clasped her hands and prayed
That saved she might be;
And she thought of Christ, who still’d the wave
On the Lake of Galilee.
And fast through the midnight dark and drear,
Through the whistling sleet and snow,
Like a sheeted ghost the vessel swept,
Towards the reef of Norman’s Woe.
And even [misprint for ‘ever’] the fitful gusts between
A sound came from the land;
It was the sound of the trampling surf,
On the rocks and the hard sea-sand.
The breakers were right beneath her bows,
She drifted a dreary wreck,
And a whooping billow swept the crew
Like icicles from her deck.
She struck where the white and fleecy waves
Look’d soft as carded wool,
But the cruel rocks, they gored her side
Like the horns of an angry bull.
Her rattling shrouds, all sheath’d in ice,
With the masts went by the board;
Like a vessel of glass, she stove and sank,
Ho! ho! the breakers roar’d!
At day-break, on the bleak sea-beach,
A fisherman stood aghast,
To see the form of a maiden fair,
Lash’d close to a drifting mast.
The salt sea was frozen on her breast,
The salt tears in her eyes;
And he saw her hair, like the brown sea-weed,
On the billows fall and rise.
Such was the wreck of the Hesperus,
In the midnight and the snow!
Christ save us all from a death like this
On the reef of Norman’s Woe!
The earliest occurrence of the phrase that I have found is from the account of a baseball match between Burlington and Rockford, published in the Rockford Daily Republic (Rockford, Illinois) of Wednesday 14th July 1897:
Up to the eighth inning the score stood 18 to 2 and the long, lank Mr. Coons who gravitated the globular bunch of horsehide and rubber for Burlington looked like the wreck of the Hesperus. There was a hunted look in his well eye like a stag party at Hudson Bay.
The second-earliest occurrence of the phrase that I have found is from one of the unconnected paragraphs making up The Tabasco Column, in The Oregon Daily Journal (Portland, Oregon) of Friday 26th December 1902:
Morrison street looks like the wreck of the Hesperus in 1492.
The phrase then occurs in The Daily Nonpareil (Council Bluffs, Iowa) of Saturday 14th February 1903:
The unusual and most demnible scarcity of hired girls caused some queer complications in Council Bluffs society nowadays. There be women in the social limelight who could import a ship load of girls with their pin money; but just the same they are girlless and alone in a cruel land.
One of Council Bluffs very nicest women was scrubbing the hall the other day. She had on her oldest gown and a rag about her head and to tell the truth she looked a good deal like the wreck of the Hesperus.
The following is from the column Cupola Sketches, by Byron Williams, published in The Daily Republican (Belvidere, Illinois) of Thursday 28th January 1904:
A SMALL HOT DOG.
A small, hot dog is said to have almost wrecked a society event in Gotham! Lucky it wasn’t a small, hot mouse or the said society event would have looked like the wreck of the Hesperus in seven seconds!
IN BRITISH ENGLISH
The earliest British-English use that I have found is from Football Fever, by Abner T. Lyall, published in The Courier and Argus (Dundee, Angus, Scotland) of Saturday 30th August 1919:
The average younker I’ve seen takes to kicking a ball or anything else kickable at an early age. The great players have, I’m told, sprung up from the side streets, where they did their boyhood’s kicking to the terror of neighbours, and earned many parental wallopings though poppa probably did the same before them. I’ve been put wise to the evolution of the player from that stage. He develops the tricks of the game and goes through the school of hard knocks. A fond mother may send out her cherub all dressed up like Lord Fauntleroy, but it’s a cokernut to a banana remnant that little Willie comes back like the wreck of the Hesperus. He’s been playing football with Jimmy round the corner. That’s the kid kicker.
IN AUSTRALIAN ENGLISH
The earliest Australian-English use that I have found is from The Fable of The Tonsorial Artist Who Played Checkers, published in The Leader (Melbourne, Victoria) of Saturday 3rd December 1910:
Mr. John Best relates the following tragic episode of a suburban barber who thought he could play draughts:—
John played the First Game. It was an Old Fourteenth, so Familiar to the Expert that it is played in serious contests only to give the Mind a little Relaxation. The Barber had the Black Pieces and Cheerfully allowed the Big Shot. His Game ended like the Wreck of the Hesperus.