In his memoir, "Power Forward: My Presidential Education," Reggie Love, now 33, explained what it was like to crisscross the nation with Obama, buying his clothes, carrying his luggage, babysitting his children, and serving his meals.
"I was his DJ, his Kindle, his travel agent, his valet, his daughters' basketball coach, his messenger, his punching bag, his alarm clock, his vending machine, his chief of stuff, his note passer, his spades partner, his party planner, his workout partner, his caterer, his small forward, his buffer, his gatekeeper, his surrogate son, and ultimately, improbably, luckily, his friend," Love wrote.
While the clothes didn't necessarily make the man, Love notes that Obama's attire made "a vital and intractable impression."
"We both had to learn how to dress the part. Because the impression we made could mean the difference between a yes or a no vote," Love wrote.
Unlike other candidates during the 2007 presidential campaign, Obama, a US senator at the time, didn't have a wardrobe consultant or stylist, according to Love.
"More often than not, that job fell to me. He would dress, and then ask my opinion. I think this was less because he valued my take on fashion and more because I was the only person around," Love wrote.
"'Looking sharp,' I'd say or 'Your tie's a little off.' And if this was ahead of a debate or a major speech, we'd fist bump before he hit the stage."
And while Michelle Obama is known for her impeccable fashion sense, Love notes that the staff had to wean Obama off of "wearing his BlackBerry on his belt like a beeper."
From the suit jacket everyone hated to buying the perfect shoes, here are some of the times Love styled America's future president.
'The man was particular about his feet'
During the March primaries, Obama was scheduled to speak in front of a crowd at Penn State and visit agriculture facilities on campus.
"We were in Central Pennsylvania and it would have been a shame to come all that way and not visit a dairy farm or two. We were advised to be prepared, and so I had been put in charge of procuring boots for the candidate," Love wrote.
Therefore, Love went on a hunt to find pasture-appropriate footwear, "the perfect boot with the perfect fit and look."
"I phoned several shops, ordering a bunch of pairs in different sizes, 11, 11.5," Love wrote.
Love ended up finding a pair of light brown Timberland steel-toes for Obama ahead of the Penn State event.
"I kept them on the plane for the duration of the campaign, just in case any surprise farm visits managed to find their way onto the schedule," Love wrote.
According to Love, shoes were the biggest challenge for Obama.
"The man was particular about his feet. They had to look a certain way, feel a certain way. Anytime he couldn't wear his favored dress flats, it was an issue."
Love notes that in certain photographs Obama's favorite dress shoes had holes in the soles from all the campaigning he did wearing them.
The suit jacket everyone hated
On the campaign trail there was one particular suit the staff hated to see Obama in.
"It was the suit without any love except from the candidate. Until the day it sort of got 'left behind' in New Hampshire," Love wrote.
As Love describes in his memoir, nothing went unnoticed by Obama, and the candidate began asking his staff for the whereabouts of his beloved suit jacket.
"There was a lot of: 'Where's the jacket?' 'I think Marvin must have taken it.' 'I thought you had the jacket.' 'Do you have the jacket?'"
"By the time the jacket was reunited with its pants, I think the senator had gotten the message about the suit," Love wrote.
'I'm a little frumpy'
"I heard they were cracking on my jeans!" Obama said to NBC "Today" anchor Meredith Vieira after she asked him about the well-worn jeans he sported during the 2009 All-Star game.
Vieira asked, "You are married to one of the most fashionable women in the world. Do you want to defend the pants?"
"No. Here's my attitude," Obama quipped.
"Michelle, she looks fabulous. I'm a little frumpy. Basically, up until two years ago , I only had four suits ... I hate to shop. Those jeans are comfortable, and for those of you who want your president to look great in his tight jeans, I’m sorry ... I'm not the guy."
Earlier this year, when asked how many suits his staff puts out each morning, Obama explained that he selects his clothing.
"Well, they don't put out suits," Obama told comedian Jerry Seinfeld on the latest season of "Comedians in Cars Getting Coffee."
"I have a closet just like normal people."
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