In this episode of New Chapters, British fashion designer and entrepreneur Amanda Wakeley OBE shares her remarkable story. Known for dressing some of the most iconic women of our time – including Princess Diana – Amanda opens up about life behind the glamour, and the resilience and reinvention that carried her through grief.
She reflects on the brutal reality of losing both her eponymous brand and her beloved brother within weeks, and how being forced off the hamster wheel after 30 years of entrepreneurial survival mode became the best thing that could have happened. Amanda also reveals what it was really like to design for Princess Diana and why their connection was so unique.
In this conversation, she talks about embracing what her grief therapist called “the fertile void” – slowing down to allow new creativity and meaning to emerge. Today, Amanda is entering an exciting new chapter: podcasting, content creation, and finally writing the book she always wanted to.
This is an episode about style, survival, and starting again – and why sometimes the most difficult endings can open the door to the most inspiring new beginnings.
Proudly sponsored by Mylands: www.mylands.com
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Amanda: @amandawakeley
Edit and graphics by Josh @ Knew Kid Media - @knewkidmedia
(01:08) Introduction to Amanda
(01:50) A passion for making women feel the best version of themselves
(02:12) Creating a podcast out of the beginnings of a book
(03:48) ‘Wakeley wellbeing’ evenings(05:13) Being hit by the juggernaut of losing her brand and her brother two weeks later
(06:05) Being forced to stop
(06:18) Being in survival mode for 30 years as an entrepreneur
(07:59) Now never been busier
(08:02) A chart topping podcast ‘Amanda Wakeley: Style DNA’
(08:27) Creating ‘Friday Night Fashion’ on YouTube with Jo Elvin
(09:38) Early years at Cheltenham Ladies College
(11:55) Modelling in New York and how moving to America shaped her work ethic and positivity
(12:34) Parents who gave her wings to fly and encouraged risk-taking
(14:26) Why modelling in trunk shows was so transformative
(14:41) The early threads of her label – influenced by Henry Lear (‘the Joseph of NY)
(16:00) Divorce and taking a tipex pen to her address book
(17:11) Princess Diana retiring from public life wearing Amanda Wakeley
(18:28) Being introduced to Diana by Deputy Editor of Vogue, Anna Harvey
(18:58) Living in my design studio – like a scene from Sex and The City
(19:49) Diana being fashionably early to appointments(20:45) Princess Diana and Princess Catherine would have adored each other
(21:23) Dressing Hollywood royalty including Angelina Jolie and Beyonce
(23:38) How dressing ordinary women and making them feel extraordinary gave her the most joy(25:15) How covid killed her business
(27:30) Why being pushed off the hamster wheel openened up an unbelievable new chapter(29:32) On therapy with the ‘Goddess of Grief’, Julia Samuel, and embracing the ‘fertile void’
(31:45) Losing her brother to a brain tumour
(32:48) Being awarded an OBE
(33:47) Rapidfire ‘this or that’ round
(38:06) On quality over quantity in all things – food, fashion etc
(38:46) Celebrating the #reware movement away from fast fashion
(40:26) How her life resembles a cross between Sex and The City and The Crown
(41:13) Why she regrets not writing a diary
(41:18) Finally writing her book ‘Style DNA’ in her next chapter
(41:48) Goodbyes
