After a few trips to Australia earlier in the year, it was time for another OTOT reunion – though this time it was Angela’s turn to make the long-haul flight, and of course she timed it impeccably to arrive the day before one of the biggest and most glamorous days of British racing: the Epsom Oaks.

Epsom Downs in all its glory.

Epsom Downs in all its glory.

Along with being the start of Britain’s summer of racing, Investec Oaks Day also features a competitive best dressed event, sponsored by the very fashionable Harvey Nichols, where the winner is awarded £5,000 to spend at the Knightsbridge department store.

It’s a raceday and a competition I know well, Epsom having been the scene of some of my biggest best dressed wins (in 2009 and 2012), so I suggested we aim for a more polished, elegant look, especially as Mariella Tandy, from UK magazine Tatler, had been given the task of choosing the winner. Angela created a ladylike peach dress embellished with jewels especially for the occasion, accessorised with a glossy black headpiece. Meanwhile I let down the hem of my bargain Singapore buy (a vivid cobalt blue frock from Southaven) to a more acceptable length, and paired it with “Shelley” from my SS14 collection and matching orange suede sandals.

Friend of OTOT and sometime Instagram contributor, Kelli Odell, was also in town and joined us for a day at the track, donning her gorgeous Flemington Fashions on the Field first runner-up outfit to enter the competition.

L-R: Lisa, Angela and Kelli at the Investec Oaks at Epsom Downs. Photo from www.dailymail.co.uk.

L-R: Lisa, Angela and Kelli at the Investec Oaks at Epsom Downs. Photo from www.dailymail.co.uk.

In previous years’ competitions, the finalist line-up was an obvious choice, however this year’s judging seemed to go against the grain. On a spectacularly sunny summer’s day, monochrome ensembles unexpectedly featured heavily among the finalists, and it was left to Kelli – in the most colourful and eye-catching outfit of the chosen few – to represent Australia in the best dressed competition.

The semi-finalists line up before they are whittled down to five finalists.

The semi-finalists line up before they are whittled down to five finalists.

Unfortunately it was not to be, and Kelli missed out on making the final six. Reflecting Mariella Tandy’s own black-and-white outfit, four of the six finalists were dressed in monochromatic looks (and a fifth in grey and white), with Rosie Divito standing out in a calf-grazing, fire-engine-red frock and cream disc hat.

Judge Mariella Tandy (right) chooses her final five. Photo from investec.co.uk.

Judge Mariella Tandy (right) chooses her final five. Photo from investec.co.uk.

Being the only finalist sporting colour, it was not a surprise when she was announced as the winner, and we applaud the budget-friendly nature of her outfit, with the dress originating from asos.com and her hat from John Lewis.

Best Dressed winner Rosie Devito wears a dress from ASOS and hat from John Lewis. Photo from Epsom Downs Facebook page.

Best Dressed winner Rosie Devito wears a dress from ASOS and hat from John Lewis. Photo from Epsom Downs Facebook page.

With no wins in the fashion stakes, it was time to try and find one on the track as the main race of the day, the Investec Oaks, approached. Alas, the punting gods were not on our side and out of the seven horses we backed (yes, SEVEN), we couldn’t even manage a place return!

Wins had: 0. Fun had: infinity.

Wins had: 0. Fun had: infinity.

We left Epsom a little poorer and (most of us) quite jet-lagged, but it was a great introduction to British racing for Angela, and an enjoyable return for Kelli. Just don’t count on such great weather if you return next year, ladies!

Photos: dailymail.co.uk, investec.co.uk and Epsom Downs Racecourse Facebook page.

By Lisa Tan