With all the focus on a bride’s dress, what a groom wears can easily fade into backing vocals. But in a true duet, each player shines. For guys, there are plenty of opportunities to customize black tie or tailoring as a way to signal individuality. Single or double-breasted jacket? Peak or shawl lapel? Lace-ups or cowboy boots? Those were exactly the decisions our friend Grady Jacobsen had to make for his wedding at The Bowery Hotel last fall — and he didn’t have to make them alone.

Grady fell for his now-wife, Mac Taskey, the day he met her, during the last week of their last year at Trinity College. “She has this positive ‘I can do this’ approach to everything. It’s magnetic…I knew a long time ago that we were going to get married,” he says. College is also where they both met Benjamin Chait, their friend and ours, too (Benjamin is an exceptional stylist and frequent Todd Snyder collaborator).

Benjamin helped put Grady in touch with our Head of Haberdashery, Alex Young, to realize his dream of vintage New York City charm. The trio met at the Todd Snyder NoMad tailoring atelier to put together a look for the big day: a double-breasted peak lapel tuxedo jacket, slim tuxedo trousers, tuxedo shirt and ostrich leather cowboy boots — to pull in a touch of Grady’s childhood, spent growing up around horses in California.

Did you come into your Made to Measure appointment with an idea or particular inspiration in mind?

Grady: Mac and I have loved living in New York, and really wanted our wedding to reflect a kind of dark, old-school, moody New York City glamor.

Ben: Grady has great style. His look started with these beautiful ostrich leather boots he wanted; I love boots with a tux. He’s a 6’4” former football player, so he has the stature to pull off a double-breasted tuxedo in a handsome way, and I knew a peak lapel would make the bone structure in his face pop. Plus, I knew what Mac was going to wear — Grady had no idea — and their peak lapels really worked together.

Grady: I was originally thinking a shawl collar, but Ben and Alex both pushed for the peak. I definitely like it better.

Grady, had you ever gotten a made-to-measure garment before?

Grady: I’ve gotten made-to-measure suits from other places, but this felt less corporate and more personal. I’ve never had a shirt made for me before…I have wider shoulders, and normally it’s hard to find a shirt that fits well, so this was fantastic. For a lot of people, this is the one time in their life they’ll do a custom look, and since you’ll have the pictures forever, you want it to fit right, look good and feel like you.

Alex and Ben, how do you approach the Made to Measure and styling process?

Alex: Sometimes people, especially men, can feel tense when it comes to not knowing something. So I don’t talk about tailoring for the first 15 minutes of an appointment; I just find out about who they are, to get them into a comfort zone where they can express themselves. My first questions are always ‘What’s happening, who’s involved, where, and why?’

Ben: Yeah, and if you don’t know where to start, just go in and ask to see everything and try it all on: skinny pants, wide pants, single-breasted, double-breasted, peak, shawl…all their options. You don’t need to know the terms, but that way you’ll see what works.

Alex: Ben acting as Grady’s stylist was really helpful because it let me focus on the details and fit. He kept Grady comfortable and had a vision of his own for him. It made our job way easier.

Ben: Seriously, the team at Todd is so helpful. Alex overseeing everything, pulling all of the options before Grady arrived…guys are afraid to ask for things, and the work of a team like this really reduces that friction.

What were your favorite details of the final look?

Grady: Ben had the great idea of embroidering Mac’s name on the cuff of the shirt in orange, her favorite color, instead of a monogram. It was a great little surprise for that first look together. Ben and Alex also added an extra button to the shirt, because I have an indented chest — if I were dancing or pulled my shoulders back, it would pull that space open and show my skin. It was such a wonderful thing that I never would have considered.

Ben: Yeah, when we were fitting his shirt, you could see straight inside. I realized we needed to add a secret button to keep it shut…that’s a trick of the trade I picked up in my costume design work. Only he knew it was there, and it dealt with the problem, so he didn’t have to worry about anything showing in photographs. Tailoring makes such a huge difference, and it’s wonderful that Todd offers that…it makes something really look like it’s yours.

Alex: We also focused on the shape of the back of the shirt, to make sure it was tapered so it wouldn’t billow, and the right collar shape. We wanted it to sit under the lapel so it wouldn’t flare. These are all areas where the personality in the event comes out. It’s our job to get it right.

Any advice for other prospective grooms?

Grady: I’ll let the other guys speak to the clothes, but getting involved in the wedding planning is so much fun, and makes the day so much more meaningful. Not to mention it takes work off your fiancé’s plate if you’re helping.

Ben: Bring a reference photo. You can say, “I want the swagger of Jimi Hendrix, or the timelessness of Sean Connery in James Bond,” and then show a photo. Photos prevent the kind of miscommunication that can happen with words alone. Oh, and I always tell both clients and friends to get two shirts. There are bright lights, you’re moving around a lot, you’re sweaty and nervous, things might spill…you want a backup. Oh, and if you’re a bigger guy, go with a bigger bowtie for balance. But most importantly, always wear black dress socks that go to the knee. 

Alex: It’s easy to get overwhelmed, but trust your gut. Trust what you want, and let us help achieve it for you. And just have fun. Making custom clothing really is a luxurious thing to do, and it should absolutely be a rewarding, fun experience.

Ben: On the subject of fun…if you’re getting a garment made, don’t hesitate to do everything at the fitting that you would at the wedding — have fun in it. Sit, kneel, dance, hug…you want to be certain everything fits comfortably in real-world situations.

Alex: At the end of the day, we’re honored by the fact that someone has chosen us to make their clothing for their wedding. We really respect everything it means.