Chester A. Arthur was known to have 80 pairs of pants in his closet at the White House and changed several times a day. His nicknames, “Elegant Arthur” and “The Gentleman Boss” were earned from his commitment to dressing up for the job, and many rightfully claimed he “looked like a president”. In fact, upon winning the election in 1881, he went directly to Brooks Brothers and dropped a cool $726 on new duds (roughly $14,000 when adjusted for inflation).

Perhaps no president can live up to the natty stylings of our 21st President, but most did have style all their own. Teddy Roosevelt’s c-bridge pince-nez added a sophisticated element to his Rough Rider cowboy persona. Harry Truman, a former haberdashery owner, was reportedly “addicted to two-toned shoes” and his handkerchief would have four, even five peaks, as if he had always just picked up his coat from a dry cleaner. Ike was the first commander-in-chief to wear a Rolex, a 1951 yellow gold Datejust, a watch his successor incidentally was also very fond of (his, of course, was a birthday gift from Marilyn Monroe). Lyndon Johnson, while not the most sartorially fluent, did speak to his tailor directly, and it’s hard to top Reagan’s movie star style, but George W. Bush was right up there on the best-dressed list with his large Texan buckles and crisp white dress shirts.

It’s been well over a year since Barack Obama took office, but his personal style is still rather hard to nail down. When Lisa Jack’s photos of Obama 30 years ago during his brief stint at Occidental College exploded onto the internet, we all got a glimpse of Barry’s inner style. He oozed cool. His hair was big. He had style. Bomber jackets with fur collars, tight jeans, a bracelet, and a panama hat helped us understand the stylish side of our President that has since completely vanished from view.

Once Obama transferred from the palm tree laden campus in East L.A. to Columbia University, all of the sudden smooth Barry became a geeky policy wonk. He cut his hair, traded in his bracelet for a calculator watch, and his leather jacket for a Member’s Only jacket. (Kids: this was a pre-ironic and pre-Justin Timberlake Member’s Only.) From his Ivy League years on, Obama has embraced a decidedly utilitarian, and decidedly nerdy style. Where did the cool guy go? We’re not saying he needs to pull out some bespoke cowboy boots a la Bush, we’re just asking for a little flare here and there. In an effort to help the president get back on track, a few pointers.

Accessorize with classic pieces. Nearly every Kennedy endorsed your presidency, you would think just one of them would be sober enough to tell you those wrap-around Maui Jim sunglasses are a major buzz kill. Even your Vice President has the sense to wear classic Ray Ban aviators and still look like a “big f-ing deal”.

Lose the Soccer Dad jeans. And those bright white sneakers. We know your wife knows where every J.Crew is in the Washington D.C. metropolitan area, would it kill her to pick you up some decent denim? If you’re not comfortable in jeans, don’t wear them.

Dress well on the golf course. Cargo pants are not appropriate for golf (and in terms of being president, they’re a big fat no-no all around.)

A cell phone holster is a modern day pocket protector. You are the president, not Glenn from Accounts Payable, put your phone in your pocket.

White tie goes with tails. If you do happen to get reelected, this might be the time for us to tell you that white tie goes with tails, so please don’t wear a white bow tie with your tuxedo unless you intend to go all the way. It’ll be the beginning of a presidential term, not the junior prom.

Square toed is square. The irony isn’t lost on us that you’re the first president to request a square-toed shoe from presidential shoe maker Johnston & Murphy. Take a cue from Bill Clinton who had a special edition blue suede loafer made in recognition of his love for playing the sax.

It’s a tough assignment to dress like a president and not like a king, especially during an economic period of instability, but we’re not asking you for much, just a little flair.