My personal style signifier is wearing a dress hat, either vintage or modern but always handmade and carefully crafted. I have more than 50 dress hats – from fedoras to cowboy hats to straw boaters. They are the ultimate form of self-expression. The first top hat I ever bought was an early ’20s shape, and I still wear it – it goes really well with ’30s white tie and tails. I also have a few from an incredible young maker in Australia called Blakesby Hats, as well as Stetson in the US, who revolutionised the cowboy hat.

Wellington’s detachable collars from RJW Shirts
Wellington’s detachable collars from RJW Shirts © Timothy O’Connell

The last thing I bought and loved was a series of detachable collars from RJW Shirts in Australia. They have a variety of historic designs that are both board-stiff and extremely comfortable – even though that sounds like a contradiction – and washable. As a performer, and somebody who goes to a fair amount of events, having washable collars is really important.

When I need to feel inspired, I listen to Fats Waller, the great American pianist and songwriter, who co-wrote hundreds of songs but was very well known for his fiery stride piano playing and his humorous repartee. So my band takes a leaf out of his book as far as the feel and the sound goes. Also The Boswell Sisters, one of the ultimate female vocal groups of the ’20s and ’30s. There’s so much to hear in their songs.

His vintage New York cab replica
His vintage New York cab replica © Timothy O’Connell

The place that means a lot to me is England. My mum is from Jamaica, so I’ve grown up hearing so much about the place, and I remember being enamoured with London the first time I visited. I’ve had the pleasure of performing at The Roundhouse and attending Goodwood Revival, which is the convergence of my childhood love of Britain with my appreciation of vintage culture and history.

Red Carpet Treatment, by Joe Boatner’s Ink Spots
Red Carpet Treatment, by Joe Boatner’s Ink Spots © Timothy O’Connell

And the best souvenir I’ve brought home is The Ink Spots on vinyl, from a secondhand store in Cold Spring, up the Hudson from New York City. They were part of a vocal legacy in early music and jazz, throughout the ’20s, ’30s and ’40s; groups who took the tradition of gospel and the black church and brought it into a more secular setting. They are less well known than some of the other groups of that time, but they have some real gems. I’m a bit of a  record collector, mostly 78s and a few 45s.

The podcast I’m listening to is The Greatest Generation, which is a Star Trek podcast. Even though I’m obsessed with music, fashion and art, I’m also very into the magical nerdery of sci-fi. There’s still so much to learn about it; the journey never ends. I like a mental vacation – and it’s a nice way to appreciate a thing you already love.

Fred Astaire in the 1935 film Top Hat
Fred Astaire in the 1935 film Top Hat © Ullstein Bild via Getty Images

My style icons are Fred Astaire, the ultimate song and dance man of his time, who introduced so many songs that are standards within the jazz canon; and Duke Ellington. Where Astaire was an interpreter, Ellington was creating symphonies that basically summed up the experience of black America. And they both had such sharp, effortless style. The ’30s are widely considered to be the golden age of menswear, and for me it’s really where I love to live: the width of the lapels and the trousers, the cuts of the jackets, the hat styles… It’s all so perfect. And both Astaire and Ellington were at their peak in the ’30s.

His c1930 Lyon and Healy cornet and Shure Super 55 microphone
His c1930 Lyon and Healy cornet and Shure Super 55 microphone © Timothy O’Connell

I’ve recently rediscovered The Reluctant Dragon. I’ve been going through the Disney+ vault, and I came across this short film that I loved to watch as a child.

The Louis Armstrong portrait given to Wellington
The Louis Armstrong portrait given to Wellington © Timothy O’Connell

The best gift I’ve received is a painting of Louis Armstrong, given to me by the grandson of the pianist Marty Napoleon, who used to play with him. It’s not a promo photo, but him in the midst of playing his trumpet, sweat pouring down his face. It’s just so beautiful, of the man who gave us our sense of rhythm and the brilliance of jazz.

His collection of modern and vintage vermouths 
His collection of modern and vintage vermouths  © Timothy O’Connell

In my fridge you’ll always find an array of cheeses – something simple like Wisconsin cheddar or goat’s cheese – and an assortment of jams and jellies from places like Fortnum & Mason. As a kid, my mum and I would always have afternoon tea together a few times a week – usually tea and crackers and cheese and jam. You’ve also always got to have vermouth in the fridge too, if you’re serious about making cocktails. My go-tos are Manhattans, Negronis or, my favourite, an Old Pal, which is Campari, rye and vermouth.

Wellington loves vintage culture and history
Wellington loves vintage culture and history © Timothy O’Connell

An object I would never part with is my ’30s white tie and tails suit. I found it at Cobblestones Vintage, in the East Village, and it’s in mint condition. It’s navy wool, with tails going down to the calf and trousers that are super-high. I wear it to perform, or for a special dinner occasion.

The last music I downloaded was a great little song called “Opus One” by The Mills Brothers. It was composed in 1943 and there’s not much to it, but it’s a case in point of their greatness. The lyrics are very much in the vein of what you hear in hip-hop from the ’70s forward, which is basically references [to other artists].

His collection of bow ties
His collection of bow ties © Timothy O’Connell

I have a collection of ties and bow ties – I recently had to purchase a second rack to fit them all. I have a mix of vintage and new ones, usually from Ralph Lauren, Paul Stuart and Kent & Curwen. It doesn’t matter what stage of style you are at, or whether you’re building a wardrobe – you can dress up or down any outfit with the right accessories. And they are often the most affordable things to purchase, as you can get a lot of mileage out of a tie.

Wellington’s calico cat and double-breasted trench coat
Wellington’s calico cat and double-breasted trench coat © Timothy O’Connell

An indulgence I would never forgo is digestive biscuits, usually the dark chocolate ones by McVities, which I have with tea. I also enjoy Tim Tams – the man behind Blakesby Hats sent me a stash with my last purchase, an incredible wide western hat from Australia.

The one artist whose work I would collect if I could is Archibald Motley. If you’ve ever wanted to know what a party was like based on a painting, he’s your guy. We hear a lot about the past through historical accounts and they’re often from the mouth of the establishment, or whatever the dominant class is. But, for African-Americans, so much of our history is verbal, so to have an artist like Archibald Motley paint their history, their reality, it’s a really powerful thing. I have a print of Gettin’ Religion on my wall.

His white Cole Haan buck shoes 
His white Cole Haan buck shoes  © Timothy O’Connell

The last item of clothing I added to my wardrobe is a pair of cream buck shoes by Cole Haan. I walked into Slone Vintage in Los Angeles, and there they were, in gorgeous condition, and they fit like a glove. I actually got quite a few things from the same visit – a black double-breasted trench coat, which is a little film noir, and a pair of ’40s navy blue pleat-front trousers with a shadow overcheck.

The beauty staple I’m never without is the fragrance Juniper Sling by Penhaligon’s. I started working with them in 2020, but they were a company that I wanted to have on my dressing table for a long time. They have such a jaw-dropping aesthetic and legacy. The scent is very much gin-adjacent – it’s sweet, musky and light enough to wear even on a hot day.

His collection of straw boaters hangs on a wall
His collection of straw boaters hangs on a wall © Timothy O’Connell
Blakesby Hats custom western hat
Blakesby Hats custom western hat © Timothy O’Connell

The works of art that changed everything for me are MGM musicals like Singin’ in the Rain or the RKO musicals Flying Down to Rio and The Gay Divorcee. They gave me a whole sense of performance. There’s often an unacknowledged thread between musical theatre and early jazz, which is essentially early pop music. So it was a perfect learning ground – like jazz university.

My grooming guru is Michael Haar, who owns Haar & Co Barbershop in the West Village. He is a born and raised New Yorker from Queens, and he understands hospitality and attention to detail. His shop feels warm and welcoming, a home away from home. My hair is not a difficult thing to do – I basically shave my head – so if I’m going to do it anywhere, I’ll do it as part of a beautiful experience.

The best bit of advice I ever received was from Murray Hill, a fellow friend in showbiz, who said: “If you don’t see yourself represented, represent yourself.” I always thought it was a powerful thing to impart to others who don’t always feel comfortable walking into a room or starting on a subject that isn’t already being talked about. It may suck, there may be that tokenism, but you’ve got to do it.

The best gift I’ve given is a series of four framed patent illustrations related to the carousel, which I gave to my partner. There’s a whole crew of us who are obsessed with carousels, whether that be the mechanics, the design, the construction, the history or the music.

Dandy Welllington in his living room
Dandy Welllington in his living room © Timothy O’Connell

My favourite room in my house is the living room – it’s where tons of family functions happen, where the Christmas tree goes, but it’s also a place of quiet. You can sit in one of the chairs and fall asleep with a book. And there’s a piano, so there have been many concerts too.

Assorted framed prints, posters and postcards from Wellington’s collection
Assorted framed prints, posters and postcards from Wellington’s collection © Timothy O’Connell

In another life, I would have been an architect. When I was young, I loved playing with Lego – I was always building stuff and thinking about construction and design. And growing up in Harlem, surrounded by all these beautiful brownstones and buildings, I don’t know how you can’t appreciate architecture.

My favourite building is Sylvan Terrace in Harlem. It’s a street that’s just off of St Nicholas Avenue and goes up to Morris-Jumel Mansion. It’s one of the most unique streets in New York City, with beautiful cobblestones and big wooden homes, most of which were built in 1882. It’s an incredible little landmark.

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