The Foundations: Shoes
"Starting Strong with Ivy Style Footwear That Works for You"
Foundations is part of a series where I walk you through building a wardrobe from the ground up.
In the first installment of the series, we’re starting with shoes.
Shoes are the foundation of your whole wardrobe. They set the tone for how you show up, and when you’re a bigger guy, that base matters.
If you're used to Rockports or tennis shoes, the price of a good pair of dress shoes can feel like a gut punch. I get it. But here's the deal: you're not just buying shoes, you're investing in presence, posture, and polish.
You won’t find “10 Must-Have Shoes Every Man Needs” posts here. I’m not interested in one-size-fits-all advice. I don’t know your exact tastes, lifestyle, or goals. What I do know is what’s worked (and hasn’t worked) for me and I’ll share that with you straight.
A friend once told me: Never cheap out on anything that separates you from the ground. That means beds, tires, and shoes. Especially shoes.
My Sock Game
I always wear knee-high socks when wearing trousers. My go-to? Falke, a German brand that holds up, literally. Even with strong calves, they stay up most of the day. Occasionally I’ll adjust them, but they’re the best I’ve found so far.
No U.S. sock recommendations yet, but I’m always on the lookout. If you have some, please let me know!
Penny Loafers
These were my first “adult” dress shoes: rubber-soled, burgundy penny loafers from Morjas. They are okay, but the width really gets to me after a full day.
Penny loafers work well in the spring, summer and fall. The look is a classic, clean Ivy style with a causal polish.
If you’re looking for something more dressed up and still a loafer, tassel loafers may be your best friends.
A Little Loafer History
Penny loafers are Ivy through and through. Clean lines, no laces, just effortless polish.
In the ’50s and ’60s, Ivy League guys wore them with everything from chinos to flannel trousers. G.H. Bass introduced the Weejun in 1936, now the go to for Ivy loafers.
If you’re a man of size, loafers are your friend. No squeezing into tight eyelets. Just slide in and roll. If you've got the right pair, they can be a godsend.
Derbies
Open-laced and a little more relaxed than Oxfords.
Styling: Great with cords, flannel, or dark denim
My Pair: Brown Morjas (they look burgundy in low light)
Downside: Terrible for my wide feet + bunions
I’ve tried stretchers, sprays, everything. Still can’t wear them all day. I’ll be replacing them with something that fits better soon.
They’re beautiful shoes though and if they fit, I would absolutely keep them and wear them every other day.
Unlined Penny Loafers
I bought a suede pair from Carmina with rubber soles for summer. I thought I’d wear them sockless. Big mistake. If you sweat like me, always wear socks.
Real-World Shoe Tips for Men of Size
1. Rubber Soles Matter
If it rains where you live, rubber soles are your friend. Still slippery in snow, but better than leather.
2. Know Your Size
Use a Brannock device and get your length + width in centimeters. Always try shoes on late in the day because there’s a big difference in how they’ll fit.
Also, sizes across all companies are not going to be the same. So just because you wear a size 11 in one, doesn’t mean you’ll be the same in other sizes.
Additionally, a lot of companies that do Made To Measure (MTM) or custom shoes have a no refund policy, so make sure you’re getting the right thing before you order!
3. Width Is Everything
If you have wide feet and bunions, forget standard sizes.
Look for:
EEE or EEEE widths
Made-to-measure or bespoke
Brands like Alden and Allen Edmonds if you’re in the U.S.
⚠️ Don’t order custom shoes online if you’ve never worn the brand before.
4. Match Socks to Trousers
This creates a clean line and elongates the leg. A subtle trick that really helps on our frame.
5. Always Use a Shoe Horn
Keep a long one at home, I use the long IKEA shoe horn and have a short wooden one for travel.
6. Wear Shoes to Tailor Fittings
The tailor needs to see the shoe’s height and vamp to adjust your trouser break.
7. Take Care of Your Shoes
Use cedar shoe trees
Brush them after each wear
Weekly clean/polish with quality products like Saphir
Rotate pairs—don’t wear them back-to-back
Taking care of your shoes can really make them last a long time. The first thing I do when I get home is put my shoes in shoe trees and brush them off. Then on Sundays I sit and polish all of my shoes that I’ve worn that week. It’s really relaxing.
8. Buy the Best You Can Afford
You don’t need shell cordovan right away. But quality matters.
Cost per wear = Total cost ÷ Number of wears
Example: $350 loafers worn 200 times = $1.75 per wear
Three Mistakes I Made Early On
Let me save you some foot pain and regret. Here are three mistakes I made when I first started upgrading my shoes and what I’d do differently now.
1. Buying Shoes That Were Too Narrow Because I Liked the Style
I saw a beautiful pair of loafers, convinced myself they’d “break in,” and ignored how tight they felt. They never did. I wore them twice and they’ve been in the closet ever since. Style doesn’t matter if you’re limping.
2. Wearing New Shoes All Day Without Breaking Them In
I once wore a brand-new pair to work. Huge mistake. By dinner time, I was limping around like Frankenstein.
Break your shoes in slowly: around the house, short walks, light errands. Let the leather mold to you. Sometimes I just wear my shoes at home when working remotely. It's not like anyone will see them.
3. Assuming Rubber Soles = All-Day Comfort
Rubber is great for grip and wet weather, but it doesn’t automatically mean comfort. If the last (that’s the shape of the footbed) doesn’t match your foot, no sole will save you. Comfort starts with fit, not just material.
How I Style Penny Loafers
Penny loafers are incredibly versatile. Here are a few ways I wear mine depending on the day, the weather, or the vibe:
Chinos + OCBD + Penny Loafers
My go-to for weekend errands, going to the grocery store or Hauptbahnhof, or just walking with presence.Flannel Trousers + Sport Coat + Penny Loafers
This is grown-man Ivy. Whether it’s dinner out, a meeting or day at work, this combo just works. Clean, classic, and sharp without being stiff.
These shoes are workhorses if you treat them right.
Final Thoughts: What I Recommend
Look for shoes that are:
Brown, burgundy, or dark suede
Penny loafers, derbies, or suede Oxfords
Darker than your trousers
Comfortable at the end of the day
Ready-to-wear is tricky, custom is better for wide feet
Made in the USA or the EU if possible
If it's from abroad and under $800 you can avoid import tariffs for now.
Right for your weather and lifestyle
Non dress shoes: Built to take a beating, like Bean Boots in the winter or camp mocs in the summer
My Bean Boot rubber boots are go-to dog-walkers and rainy-day champs. They remind me of childhood, being outside, and having fun :)
Wrapping It Up
Shoes are where your style story starts. And as a man of size, you deserve footwear that supports you, literally and stylistically.
Don’t settle for pain. Don’t settle for “good enough.” You’re not building a costume, you’re building a wardrobe that reflects who you are: solid, intentional, and grown.
Start with one pair that fits you well and makes you feel something. Proud. Polished. Present. That’s the Ivy spirit.
If you’ve got questions, experiences, or even horror stories from the shoe aisle, I want to hear them.
Drop a comment or shoot me a message, I’m here to help you walk taller.
Let’s keep stepping forward, one well-dressed foot at a time.
Community Reminder
This space is for open, supportive conversations about weight, self-worth, and style. Please be respectful. Trolling, harassment, or hate speech will be removed to protect this community. Thanks for being here and treating everyone with kindness!
If I mention a product, it’s because I use it myself or think it’s worth your time. I don’t get paid for any links you click, and I don’t make commission from them.
I also love your friend’s piece of advice.
I can vouch for Quoddy and I live in their suede bluchers in the summer.
Well made shoes are absolutely an investment in both oneself and in the craft of the maker. They cost more because they last so much longer than shoes poorly made from inexpensive synthetic materials and a quality pair of shoes can usually be resoled. Unfortunately, we are forced to navigate a market dominated by planned obsolescence where virtually nothing is built to last.
Lastly, I love to hear I’m not the only shoe nerd with a Sunday polishing ritual!
Don’t cheap out on anything that separates you from the ground, I LOVE that hahaha - would add couches to the list 😂 have you tried anything from Quoddy? They do a wide range of custom sizes (and then once you know your style you can try to grab it from their annual summer sample sale in the future). I have the opposite problem, ridiculously narrow and low-volume feet. It causes its own set of problems (ie even with insoles shoes are sliding around and don’t stay on my heels) so I’m hoping to get a custom pair from Quoddy this year or next after decades of blisters!!