The Foundations: Shirts
Confidence starts with the first button
This is the third post in my foundations series. The first post was about shoes, which start the foundation, building upon that was the post about trousers
You'll find the entire series here.
Why Shirts Matter
A good shirt does more than protect your jacket. It anchors your whole look. For bigger guys, the shirt is often the first thing people notice. It’s front and center. If it fits poorly, everything else, no matter how nice, feels off.
But when it fits? That changes everything. You feel better. You look sharper. You move with more purpose.
You Deserve a Shirt That Fits You
Growing up, most of us got shirts off the rack from places like J.C. Penney or Belk. Custom clothing wasn’t even a thought.
So we made do. Scratchy fabric. Tight collars. Sleeves that went past our knuckles. Remember those days?
That’s one reason a lot of guys don’t enjoy dressing up. They’ve never experienced what it could feel like. That’s what we’re going to change.
As men of size, we deserve to look and feel our best. Dressing with intention is for all of us, not just for runway models or influencers with unlimited budgets.
What About Custom Options?
If ready-to-wear shirts fit you well, count your blessings. But if you’ve got a belly, love handles, or a body that doesn’t match a showroom mannequin, then you might need a better option.
Made-to-Measure (MTM) is the most accessible route. You can go to a local tailor, dry cleaner, or even measure yourself at home and send the numbers to a vendor. They’ll make a shirt based on you.
Bespoke is a level up. It takes more time and costs more, but every part of the shirt is made just for you. You choose the fabric, the collar shape, the cuff style, even the buttons. They cut and sew it by hand, and you go through fittings to make it perfect. Once they have your pattern, you can reorder anytime.
Start by Knowing Your Fit
Here are the key shirt measurements you should know:
Shoulders – Most important. They set the frame.
Neck – You should be able to button it comfortably.
Chest and Waist – Controls whether the shirt pulls or billows.
Sleeve Length – Should land right at the wrist.
Shirt Length – Should match your trouser rise and intended tuck style.
When these are dialed in, you feel the difference. The two most important to get right are your shoulders and your neck. Your shirt should land right at your natural shoulder line, and your collar should never choke you.
Ivy Style Shirt Terms
Button-Down Collar – The Ivy staple. A soft collar that buttons at the points. Casual but polished.
OCBD – Short for Oxford Cloth Button-Down. Thick, softens over time, and works in most situations.
Placket – The strip of fabric with the buttonholes. Adds structure.
Barrel Cuff – Straight and simple. Easy to wear with or without a jacket.
Polo Shirt – The casual alternative. Great for warm weather and weekends.
Bonus Ivy Details:
Locker Loop – That small loop on the back. Originally for gym lockers.
Box Pleat – A single pleat on the back for extra movement and ease.
Chest Pocket Styles:
Brooks Brothers – Clean and simple open pocket.
J. Press – Flap pocket with a button. Slightly more formal.
Best Materials by Season
Spring – Lightweight Oxford or broadcloth. Breathable and crisp.
Summer – Twill, linen, or broadcloth. Mix and match textures and collars.
Fall and Winter – Time to play. Flannel, heavyweight Oxford, and chambray all shine here.
Order your shirts one season ahead if you’re going MTM or bespoke.
Build a Smart Weekly Rotation
OCBDs will carry you through most of the week. I also keep:
Short sleeve shirts for summer
A dressy knit pique for layering
A mix of weights and colors for the season
Start with light blue, then college stripes, pink, and white. That order will set you up well.
Tucked or Untucked?
A tucked shirt defines your waistline and sharpens your whole look. You’ll appear more put-together, even in casual settings.
But comfort matters. Get shirts with enough room and the right hem length so they stay tucked. Learn the side tuck to manage extra fabric.
Untucked can work, especially in the summer. Just know that an untucked shirt isn’t fooling anyone. And beware of the wind—no one wants to flash their belly at a barbecue.
Give Yourself Permission
If you’ve ever walked into a department store and wondered if they even carry your size, I know how you feel. If you’ve browsed a “Big & Tall” site and felt like the models weren’t even real people, you’re not alone.
But here’s the truth: You belong here. You deserve to feel good in what you wear. You deserve to be seen and feel sharp.
That’s not vanity. That’s dignity.
Mistakes I’ve Made (So You Don’t Have To)
Know your fit. Measure yourself before you start spending. It will save you time and frustration.
Don’t overdo OCBDs. They’re great, but you’ll want some variety.
Buy trousers first. Shirt length depends on your pant rise.
Avoid shirts with stretch fabric. They wear out faster at stress points.
Skip the clearance trap. Cheap shirts that don’t fit still cost too much.
Think about fabric weight. Heavy Oxfords don’t belong at hot summer weddings.
Care for your shirts. I wash and iron mine at home. Even “no iron” shirts look better with a little care.
Get the right undershirts. I switched from white cotton tees to nude v-necks from Amazon. No lines, no show-through, cooler all year round.
Final Thoughts
Your shirt is more than just fabric. It’s the starting point for how you carry yourself through the day. When it fits right, when the fabric breathes, when the collar rolls the way you like, it changes how you feel. You stand taller. You move with confidence. You’re ready to be seen.
For bigger guys, Ivy Style is more than just a look. It shows that you take yourself seriously, that you dress with care and pride. You don’t need to shrink your body to wear great clothes. You need clothes that respect the body you already have.
Whether you’re just now stepping into better shirts or starting to invest in custom pieces, take your time. Learn what works for you. Build a wardrobe that fits your life. You’re not dressing to disappear. You’re dressing to show up.
You’ve earned it. And you’ve got this.
Let’s Talk About It
What’s the best-fitting shirt you’ve ever owned, and what made it stand out?
Have you tried made-to-measure or bespoke shirts yet? What was your experience like?
Drop a comment or shoot me a message, I’m here to help you dress with intention.
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