Ellen Degeneres in bespoke suits

The Best Suits of Ellen DeGeneres

Mastering Effortless Tailored Confidence 

Ellen DeGeneres has elevated the custom suit into her signature, an art form balancing precision tailoring with effortless ease. Whether hosting her daytime show in perfectly cuffed trousers paired with fresh sneakers or commanding red carpets in impeccable formal wear, Ellen demonstrates that true style confidence comes from clothing engineered to your exact specifications.

Her approach is masterful: At a 2014 Twitter event, she paired expertly fitted Black Watch plaid trousers with a navy tuxedo jacket featuring black satin lapels, crisp white button-down, and patent leather Oxfords—elevating classic menswear with sophisticated polish. Yet she never abandons her signature quirk: suede Chelsea boots with contrasting tan soles alongside wife Portia de Rossi's coordinated formal attire, or stone-colored lace-ups and aviators with a light grey tweed blazer for Wimbledon.

From Converse and sweater vests to Dolce & Gabbana suits and eye-catching prints, Ellen proves that custom tailoring isn't about conformity—it's about expressing authentic confidence through precision fit and personal flair. Her "Hamptons school-boy" aesthetic demonstrates what we champion at The Tailory New York: when your suit is tailored flawlessly to your body and style, you wear it with ease, personality, and unstoppable presence.

ORIGINALLY PUBLISHED: OCTOBER 10, 2014 | UPDATED: OCTOBER 15, 2025

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THE MANY SUITS OF ELLEN DEGENERES

The outfits she is seen wearing on her hilarious hit daytime TV show could be described as Hampton’s school-boy. She is often seen sporting a pair of perfectly tailored trousers, cuffed at the precise length to show off a pair of fresh sneakers.

Courtesy of Vogue Ellen DeGeneres at The 41st Annual People's Choice Awards The Best Suits of Ellen DeGeneres

Ellen DeGeneres at The 41st Annual People’s Choice Awards. Courtesy of Vogue

 

Let’s face it, whether she is wearing a button-down, sport jacket, or sweater set, Ellen always manages to look effortlessly put together.

And her more formal looks are just as flawless! From hosting an awards show, strutting her stuff on the red carpet, or being spotted out on the town with her wife Portia de Rossi, Ellen never steps a foot wrong in a tailored suit.

The Best Suits of Ellen DeGeneres
Ellen DeGeneres attends the #TGIT premiere event hosted by Twitter at Palihouse Holloway on September 20, 2014 in West Hollywood, California. Courtesy of Time Magazine

So who better to teach us a thing or two about how to wear a custom suit with serious confidence and flare? Let’s recount a few of our favorite Ellen suit looks…

This look may be a throwback, but we adore it so much that we had to include it! At a 2014 Twitter event, Ellen wore an expertly fitted pair of Black Watch plaid trousers with a navy tuxedo jacket.

Her black satin lapels amped up the elegance while her crisp white button-down maintained the signature Ellen ‘Cool and Casual’ factor. Her patent leather Oxfords complemented the satin lapels and really brought the whole look together too.


The Best Suits of Ellen DeGeneres portia de rossi ed by ellen x bergdorf goodman pop up shop28129
Ellen DeGeneres and Portia de Rossi hit New York Fashion Week on Thursday, Sept. 10, wearing perfectly matching ensembles. Courtesy of Us Weekly

We love when couples coordinate, and if any couple can pull off coordinated suits, it is this female power-couple. These simple black suits are classic, without doubt.

It wouldn’t be Ellen if there wasn’t a quirk though! While wife Portia opted for sophisticated black heels, Ellen opted for a suede Chelsea boot with a contrasting tan sole; the perfect accessory to add an element of casual to an otherwise formal look.

In the warmer weather for a Wimbledon tennis game in London, Ellen opted for a light grey suit. She teamed a tweed blazer with fitted grey trousers and a printed button-down that kept her look summery and fresh. The hilarious host completed this look with a pair of stone colored lace-ups and very on-trend aviator glasses.

Ellen is most certainly a style icon. No matter the occasion, she always looks like she has stepped off the pages of GQ. From Converse and sweater vests to Dolce and Gabbana suits and eye-catching prints, every look is worn with ease and her own special quirk. Ellen, we salute you!


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