If you’re like most guys from Bathurst and Lawrence, your dress shirt has to do a lot more than just look good for an hour.
You’re up early for Shacharis, heading to a Daf Yomi shiur, off to a business meeting in midtown, or checking on a project in Vaughan, and—if you’re lucky—maybe even a date with the rabbi later that night.
So let me ask you: why are you still wearing a shirt that doesn’t fit, doesn’t hold up, and has more creases than a kugel at Kiddush?
Hi, I’m Sam—yes, that Sam, the Suit Guy from Sam’s Menswear.
For over 25 years, I’ve been helping men from Bathurst Street to Ocean Parkway, look sharp—from real estate developers and lawyers to yeshiva bachurim and young professionals getting ready for shidduchim. I’ve dressed them all. And if you’re tired of shirts that pull in all the wrong places, or look like you borrowed them from your shver, I’m here to help.
Let’s talk about why a custom dress shirt actually matters—and how it can take you from morning seder to night seder looking sharp, feeling comfortable, and staying fresh no matter where you are.
First, let’s address the elephant in the room—tefillin creases. You know what I’m talking about. You put on tefillin, and by 9 AM, you’ve got deep lines running down your arm that scream “yeshiva bachur,” even when you’re sitting in a business meeting. If you’ve ever fought with your sleeve while wrapping, or tried to roll a cuff that feels tighter than your shvigger’s cholent, you know off-the-rack shirts don’t get it. That’s why we design custom dress shirts with enough room in the sleeves to wrap tefillin properly, but still keep them tapered so you don’t look like you’re wearing a garbage bag. Our cuffs open wide enough to make wrapping easy, and we use strong but comfortable fabrics that hold up to tefillin and still look crisp at your next meeting.
And speaking of meetings—let’s talk business. I dress a lot of guys in real estate, law, finance, and rabbi—you name it. Whether you’re meeting an investor downtown Toronto, walking a construction site in Oakville, or closing a deal on Avenue Road, you’ve got to look like you mean business. A good shirt—one that fits properly and holds its shape all day—speaks before you even open your mouth. And I don’t mean stiff, uncomfortable shirts that make you count the minutes until you can take them off. I’m talking about shirts that feel as good as they look, tailored to fit your body, layered perfectly under a blazer, and sharp enough to make a real impression. Because let’s be honest—if you’re building multi-million-dollar projects, you shouldn’t be walking around in a shirt that looks like you picked it up off the clearance rack at Yorkdale.
Now, for the yeshiva guys—I see you. You don’t want to think too much about what you’re wearing every morning, but you still want to look like a mensch. You’re sitting in shiur, running around Bathurst and Lawrence, maybe bumping into a shadchan or heading to a simcha later. You need shirts that work for all of that. That’s why I make shirts that are breathable for long days in the beis, durable enough for constant wear, and fitted so you don’t look sloppy when you run into your rosh yeshiva or future in-laws. And when Shabbos comes, we can step it up a notch—cleaner, sharper fabrics that make you look like you belong at the head table, not just in the back of the hall.
But here’s the thing—not every shirt has to look the same as the next guy’s. Even if you’re in a white shirt every day, you can still have a little personality. I do textured whites that give a clean look but with depth, blues and greys for guys who want to switch it up a bit, and even custom collars or monograms if you want something subtle but unique. These are details that make a difference, and trust me—people notice when you take care of how you look.
And yes, let’s not forget date night—because looking good for a date doesn’t mean you have to try too hard. A custom shirt that fits perfectly, with a sharp collar and clean lines, makes you look confident and put together. Whether you’re heading out to Bistro Grande, grabbing something casual on Bathurst, or joining a Shabbos meal, the right shirt says you care about yourself without looking like you’re trying too hard to impress.
If all this sounds like what you’ve been waiting for, good news—booking an appointment is easy. You can use my online system, Amelia, to pick a time that works for you. You can come to my studio, or I’ll come to you—Bathurst and Lawrence, Thornhill, Vaughan, Promenade—house calls are a real thing. We’ll sit down, figure out what you need—whether it’s for business, yeshiva, dates, or all three—pick fabrics you’ll love, and take proper measurements so when those shirts arrive, you’ll wonder why you didn’t do this sooner.
Because at the end of the day, you deserve to look good and feel comfortable—not just on Shabbos or Yom Tov, but every day. Whether you’re building deals, learning in the beis, or meeting someone special—how you show up matters. So let’s get you shirts that fit, shirts that work for you, and shirts that make you feel like the best version of yourself.
Click here to book your appointment now—and let’s get you into shirts that actually fit your life.
And if you’re tired of shirts that crease from tefillin, fit weird, and make you look like you borrowed something from your shver—you’re not alone.
Let me tell you—a custom shirt that actually fits changes everything.
