Some of the most influential players in big-money conservative politics gathered late last month to discuss governments role in society, but their focus kept shifting to a less weighty topic: Rand Pauls outfit.

The Kentucky senator and prospective GOP presidential candidate whose libertarian politics mesh with those of the billionaire megadonor brothers Charles and David Koch appeared at the annual winter meeting of the Koch donor network wearing a boxy blue blazer, faded jeans and cowboy boots.

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Some attendees commented that Pauls appearance was cavalier, said Frayda Levin, a Paul supporter and major donor who attended the conference at the Ritz-Carlton in Rancho Mirage, California. It was organized by Freedom Partners Chamber of Commerce, the nonprofit hub that oversees the Koch network. This is an older crowd and much more establishment crowd. They are used to a Romney. They are used to a Jeb Bush, Levin said.

Jeans might work for a younger audience, said another attendee, but these are old bulls who put on a tie every day to go to the office.

The sartorial criticisms hint at a potentially more serious challenge for Paul securing the backing of enough big-money donors to be competitive in a crowded Republican primary that could include prolific fundraisers such as Jeb Bush and Chris Christie.

During a Sunday afternoon speech at the Koch forum , Paul drew skepticism among some donors by touting tax breaks as a means of spurring economic growth in blighted inner cities. That stance is anathema to the brand of small-government conservatism espoused by the industrialist brothers and many of their networks donors, who object to marketplace interference. Even Levin admitted she was a bit surprised. But hes just exploring ideas right now. People didnt quite understand where he was coming from.

Donors were further put off by Pauls performance later that evening in a forum for prospective GOP presidential candidates that also featured Sens. Marco Rubio of Florida and Ted Cruz of Texas. At times slouching in a cushy arm chair, Paul, with his legs crossed, gave rambling answers that contrasted sharply with other participants.

At one point, he opposed eliminating tax benefits to the oil and gas industry from which Koch Industries, the brothers multi-national conglomerate, benefits but which the brothers philosophically oppose. Paul seemed less prepared than Rubio, who gave detailed answers and was by far the most sharply turned out of the trio (pressed Navy blue suit, crisp white shirt, red tie and American flag lapel pin). Cruz, tieless in a light blue shirt and tan sports coat, laced his remarks with one-liners.

The next day, when 100 donors participated in an informal straw poll conducted by veteran consultant Frank Luntz, Paul finished dead last. Rubio came in first, followed by Wisconsin Gov. Scott Walker, who stopped by the conference, but could not make it for the panel.

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How Rand Paul bombed at Koch brothers gathering