How did Desmond & Dempsey
come about?

When Molly and I moved in together, she always borrowed my shirts for bed. When that tired, and my shirt count was in the negatives, we started the search for some proper pajamas for her. The more we looked into the market, we felt there was a gap at the premium end for printed cotton styles. So, we set off to design our own—a brand about the pleasure of leisure.

People tend to skimp out on nice loungewear ...

I know. But when you think about it, your pajamas probably get as much wear as some of your jeans. We spend a lot of time obsessing about how what we're wearing will feel in bed and around the house. Fabric that will keep you warm, but not too warm when you're asleep. No scratchy labels. Elastic waistbands. Deep pockets so you don't lose your phone down the back of the sofa. Simple things, but ones that make a huge difference when you're trying to be comfortable. When someone designed that old band tee they didn't make decisions about the product because it was great to sleep in.

Tell me more about this hand-painting of the prints.

It's something that we have always done and will always do. It's not the most efficient way, but we love that when the product goes into production, you can still see the details of the brush strokes, for example. In recent years, we've started using lots of new techniques to create different textures within a print. In our new Elements collection, the team used the rings of an old cut tree trunk to create the print.

The brand’s mantra is celebrating life at home. What’s one thing you can share with us about the importance of enjoying slow mornings?

Since we had our daughter, all of us sitting down in the morning and having breakfast together has become a special moment and worth savoring. It also helps that I take some time to wind up in the morning—I'd rather start the morning slower and speed things up if I need to. My theory is that if you get moving too fast, it's hard to stop and get that time back, but it's easier to catch up.

How would you describe your style in five words or less?

Comfortable and warm.

What’s one item that every man needs in his closet?

A good suit. Zegna if you can afford it. I don't think it matters too much about the brand name as long as the fabric is of exceptional quality, it's altered to fit you perfectly and not too trend led. Most of us don't wear them every day, so something classic that you won't get out next year and be embarrassed about. It doesn't have to be a fully bespoke suit, but getting something off the rack altered is always worth it.

Three favorite brands, currently?

Universal Works, Stüssy and Margaret Howell.

What’s one item that you
cannot part with?

An old Carhartt jacket I've had for probably 15 years that I can't get rid of. I've repaired it many times—and I hardly ever wear it—but I can't get rid of it.

What’s something you’re looking to buy at the moment?

For ages I have been looking for the perfect black western style belt. I found a few at Our Legacy that I have my eye on.

Do you shop more online or in person?

I love browsing in person, but I am an impulse shopper. I tend to procrastinate over what I want and walk out of the shop with nothing and then buy online last minute and need it on the fastest shipping possible. I'll go months without shopping, then really go for it. If I'm overseas, definitely in person though—that's probably when I shop the most.

Where do you personally love to shop?

I have always enjoyed shopping for clothes in New York because I love walking everywhere and the people-watching is great, and it's so easy to walk without worrying about getting lost.

But more often than not, I end up shopping for homewares when we travel. I used to visit Madrid a lot when Molly and I first got together, and we would buy things for the home from the markets in La Latina, which is every Sunday. That seems to have stuck with me, and all sorts of weird things have ended up as hand luggage.

What’s a necessary
extravagance for you?

Really excellent socks. Trust me, you can tell the difference.

What is something you like to save money on or refuse to spend a lot for?

White T-shirts. I don't spend loads on those because I always spill things on myself and can't get the stains out and struggle to find anything long enough in the body. The UNIQLO U crewnecks are my go-to.

What’s something you buy in multiples?

Those white UNIQLO tees.

Which do you experience more: buyer’s remorse or regret for not buying something?

I'd definitely say, “regret for not buying something.”

What’s one shopping hack that you can let everyone know about?

Go ahead and add to your cart, then leave it and come back. Sometimes you will, sometimes you won't. Abandoning baskets online will end up saving you money.