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Entry from OED Online

pear-shaped, a. DRAFT REVISION Mar. 2003     

[< PEAR n. + SHAPED ppl. a.

    1. Shaped like a pear; tapering towards the top and rounded at the bottom. Now esp. of a person or a person's figure: wide-hipped.
 
  1731 P. MILLER Gardeners Dict. s.v. Acajou, In the Bottom of the Calyx is the Ovary, which becomes a soft Pear-shap'd Fruit. 1815 J. SMITH Panorama Sci. & Art II. 7 A pear-shaped glass vessel. 1845 N. P. WILLIS Dashes at Life with Free Pencil IV. 100 Some trifles bought of a pearshaped pawnbroker. 1890 O. WILDE Picture of Dorian Gray xi. 150 The ducal hat..was hung with pear-shaped pearls. 1926 Chambers's Jrnl. May 315/2 A sleek and pear-shaped gentleman heavily brilliantined and scented. 1941 R. HEADSTROM Adventures with Microscope (1977) v. 16 These stinging cells, or nematocysts as they are called..are small oval or pear-shaped bodies. 1993 Clothes Show Feb. 72/1 Attention to detail helps disguise a pear-shaped figure. Look for button-through styles that bring the eye to the middle of the body to draw attention away from the sides.
 

    2. Of a musical or (more often) vocal tone: rich, mellow, sonorous.
 
  1925 N.Y. Times 22 Mar. VII. 4/1 Imagine this director suggesting that you use a more pear-shaped tone in the love scene and then resort to the deeper curves for the denunciation. 1958 S. VAUGHAN in T. Cole & H. K. Chinoy Directors on Directing (rev. ed.) (1963) IV. 435 In such productions, the pearshaped tones have so little in common with the purpose of speech in life that the clever salesmanship of visual beauty is essential. 1977 C. MCCULLOUGH Thorn Birds v. 92 As he spoke to her Father Ralph's own speech became more pear-shaped, and quite lost its beguiling hint of Irishness. 1994 Billboard 20 Aug. 76/3 Hefty and pear-shaped, Walser's music..features arrangements that hearken back to Bob Wills.
 

    3. colloq. (chiefly Brit., orig. R.A.F. slang). to go (also turn) pear-shaped: to go (badly) wrong, to go awry.
 
  1983 J. ETHELL & A. PRICE Air War South Atlantic 158 There were two bangs very close together. The whole aircraft shook and things went ‘pear-shaped’ very quickly after that. The controls ceased to work, the nose started to go down. 1989 Air Forces Monthly Feb. 53/2 When a disadvantaged fighter manages to manoeuvre back into a neutral position, it is a sign to the attacker that things are already going pear-shaped. 1995 FourFourTwo Sept. 108/1 The day itself was one of those prize-winningly crappy days when everything went pear shaped. 1999 J. CASSIDY Street Life 118 Next we travelled to Bournemouth and it was there that things began to turn rather pear-shaped.