Britney and her new boyfriend David Lucardo started their trip to Las Vegas, Nevada, with a very unusual fashion statement on Friday.
Love match: Britney Spears and her new boyfriend David Lucardo went for very similar looks as they flew out of Los Angeles, California, on Friday
The 31-year-old star and her man both donned waistcoats and fedoras for their flight from Los Angeles, California to Sin City.
The Till The World Ends singer donned a dark blue waistcoat with a lace high-necked shirt and a leather ice skater skirt.
The star added black suede knee high boots that she unzipped and folded down to make them appear more like ankle boots, as well as a blue tartan fedora.
Mix and match: While the couple matched the 31-year-old's outfit did not with star donning a dark blue waistcoat with a lace high-necked shirt and a leather ice skater skirt
Taking his girlfriend's lead Ordinary Dave - as the legal firm field researcher has become known - wore a snugly fitting lighter blue waistcoat over, an also very tight, shirt with a light blue tartan tie.
History repeating: The singer likes to dress her men like her, and vice versa, as Brit and then-boyfriend Justin Timberlake infamously both wore denim outfits to the American Music Awards in 2001
Dave also donned a very similar dark fedora.
The couple's outfits evoked memories of the singer and her former boyfriend Justin Timberlake's matching fashion disaster of a decade ago.
The then couple ended up on almost every worst dressed list around the world after they donned matching all denim outfits to the American Music Awards in 2001.
Justin - who was in boy band 'NSYNC at the time - wore a denim suit jacket with flared denim pants - both of which had contrasting denim patches - with a cowboy hat made of jean material.
Britney wore a ball gown cut from denim and even accessorised it with a denim handbag.
While the image of the pair walking the carpet together in their matching denim has lasted, their romance did not, ending just one year later.
Britney has since been married twice - for one day to friend Jason Alexander and for two years to back up dancer Kevin Federline - and recently split with fiance and former manager Jason Trawick.
Justin - who now has changed his image to ensure he is on the best and not the worst dressed lists - recently married actress Jessica Biel.
Despite the failure of matching looks before, Britney seemed very happy couples dressing as she flew out to Vegas.
Britney is in final negotiations with Caesars Entertainment to have a performance residency at the Planet Hollywood Resort and Casino so no doubt the trip was not all matching outfit fun.
The singer did manage to enjoy the town while there, however, as on Sunday night she posted a a picture of her and Dave - and her manager - enjoying the Cirque du Soleil’s One Drop show.
Helping to raise funds to for the show's charity that aims to ensure people around the world get access to safe and clean water, the show certainly impressed Britney.
Meet my man: The Till The World Ends singer introduced fans to boyfriend Dave posting a picture on her Twitter of the couple watching Cirque du Soleil's One Drop show on Sunday in Las Vegas, Nevada
She tweeted: 'The @Cirque @ONEDROP show… SO WOW!! #1night1drop Watch it online & support #worldwaterday” Brit tweeted, along with a link so you too can watch and support World Water Day.'
Beaming the singer happily posed with Dave's arm around her, and the picture marks the first time the singer has publicly acknowledged her new boyfriend - whom she was first spotted with in February.
The couple did not have a lot of time to relax after the show however, flying out that same night.
Quick trip: After the show the singer and her beau flew out of Vegas
Britney split with her partner of three years, Jason, in January.
The mother-of-two recently admitted she will 'always love' her former fiance.
Britney added: 'Jason and I have decided to call off our engagement. I'll always adore him and we will remain great friends.'
The one before: The 31-year-old called off her engagement to Jason Trawick in January
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