This executive portrait of Larry Ellison, founder and CEO of Oracle, shows him looking at his very best.

Larry Ellison, founder and CEO of Oracle, whose lifestyle exudes a lavish life and style, is most worthy of a profile in style.

A true icon of tech and business, Larry Ellison lives large in business, pleasure, and personal style.  Who hasn’t heard of his mega-yachts and his recent purchase of the Hawaiian island of Lanai in 2012 for $600 million?  That island may just be the tip of the real estate iceberg for Larry Ellison.  But don’t scoff at his personal real estate holdings.  They include a mansion made to resemble a feudal Japanese village, in the Woodside hills, a tony enclave outside of San Francisco.  He also bought and combined several beachfront properties in Malibu into a mega compound.

To say that Larry Ellison is into planes and cars would be a gross understatement.  He has a fleet of the best of the best.  And, like any playboy with wild tendencies, he has “collected” women in a way that could be seen as consistent with his other expensive hobbies.

It also must be mentioned that his love of sport is legendary.  Case in point: the Americas Cup competition that he brings to San Francisco this year, with great fanfare, and with great expense.


So how does this world champion sailboat racer, jet pilot, and ruthless businessman do on matters of personal style?  Larry Ellison tends to be a style conscious man.  His clothing choices suggest that this is true.  I also remember him visiting a high-end menswear store where I worked in Chicago back in the 1990’s, and that what he purchased then was stylish clothing for a power dresser.

Larry Ellison wears a suit with the right expression. But the suit color and the black mock turtleneck miss the mark.

Recent photos of Larry Ellison suggest that he still has the knack for power dressing.  Wearing suits, especially double-breasted styles, with peak lapels convey that he looks as assertive as he is.  An executive portrait, taken when he was somewhat younger, shows him at his very best. He looked totally confident and sophisticated in a dark suit, white shirt, and red tie that compliments his complexion.

Larry has eased off on wearing ties [maybe he read my blog about ties last week?], which isn’t such a bad idea.  But the black mock turtleneck knit worn, a la Steve Jobs, in place of a dress shirt and tie, looks incredibly dated.  The black color sill hints at his assertiveness, and may even echo a sense of his avant-garde thinking.  But between the look being so closely associated with is good friend Jobs, and with the 1990’s, it is not doing him any favors.

Larry Ellison addresses the crowd at a major company event. With little contrast in his darkly colored ensemble, he doesn’t appear to carry the energy people know he actually has.

I’m also not a fan of the outfits created with his notched lapel suits worn with that black mock turtleneck knit.  No longer does he look powerful, even though he most certainly is.  This whole look ages him.  Dated styles absolutely age the wearer, and make the wearer look less agile, and more like yesterday’s news.  The notch lapel suits are fine on days when he needs to focus on listening and on thinking, and when he needs others to get the sense that he is doing those things.  But the combination is problematic.

Also, the lighter, earthier colors of the suits he’s wearing don’t seem to be agreeable with his personal coloring.  I think it’s great for him to wear suits that aren’t black or navy.  But they must match his coloring and energy.  These don’t do that, and to top it off, that darned black mock turtleneck creates an unattractive contrast level, drawing an onlooker’s eyes away from his face.

Larry Ellison, standing beside his well-tended to girlfriend, looks like he ought to find clothes that flatter him better, both in fit and in color.

Larry Ellison, standing beside his well-tended girlfriend, looks like he ought to find clothes that flatter him better, both in fit and in color.

For someone who lives in very high style, it can seem that when it comes to his personal style, Larry Ellison is easing off quite a bit.

Another important point to note about the way Larry Ellison dresses is that he’s a minimalist.  He doesn’t wear superfluous pieces of clothing.  He wears very few colors in an outfit.  Even the dated mock turtleneck is conceptually minimalistic.  But there are so many other modern and better options that he could be wearing to spruce up his look.

That we don’t see him doing this surprises me because Larry Ellison is a man who is driven by ambition, still to this day, and is renowned for his impeccable business sense.  He does not give up on anything he believes in, and clearly believes in himself!  So why is he stepping off the gas pedal when it comes to his personal style?

Many people, I imagine, will think my evaluation of Larry Ellison’s personal style is a bit harsh.  People do think that he is stylish.  He is.  But who does a man like Larry Ellison answer to about his style? He should look in the mirror and challenge himself to look as current as all of his entrepreneurial ideas.  If anyone could possibly have it all, he should.