First Upgrades
Author: Robbie Lannon
Posted on: Jun 14, 2026
First Upgrades
So you’ve decided to upgrade your wardrobe. Great. But where do you actually start?
A lot of guys make the mistake of trying to overhaul everything at once, and it usually becomes an expensive lesson. They buy the wrong shoes for their lifestyle, load up on suits they’ll wear once every few years, or chase trends they never feel comfortable wearing.
The formula I use instead is simple:
Buy Twice, Cry Once.
Let me explain.
A few years ago, one of my best friends gave me a surprisingly good piece of advice without realizing it. He had picked up a new hobby and bought a cheap starter setup instead of investing heavily right away. My mindset had always been “buy once, cry once” — buy the best version you can afford upfront so you can enjoy the best experience immediately.
But his approach made sense.
If the hobby didn’t stick, he’d only spent $50 instead of $500.
That idea stayed with me, and since 2022 it’s completely changed the way I approach wardrobe upgrades.
Pick One Category
Start small. Pick one category:
Shoes
Shirts
Pants
Jackets
Then make a modest upgrade in that area.
One of the best things you can do is thrift your way into trying something new. One of my favorite pickups to date was a thrifted pair of black penny loafers from Allen Edmonds.
Whatever category you choose, be selective.
Shoes ground your outfit. Shirts and pants can dramatically improve versatility. Jackets can become statement pieces. There’s a strong argument for prioritizing any of them depending on your lifestyle.
The important part is this: take a low-risk chance on something you’re curious about.
Thrift the shoes you’ve been eyeing but haven’t committed to.
Buy the shirt that feels slightly outside your comfort zone.
Grab a statement coat from a garage sale for next to nothing.
Experiment cheaply first.
Yes, there may be some growing pains, especially with cheaper versions. That’s intentional. The goal is to figure out whether you actually enjoy wearing the item before investing serious money into it.
If you wear it constantly and eventually wear it out, you’ve found something worth upgrading.
That’s the entire premise behind “Buy Twice, Cry Once.”
Buy the affordable version first. If it earns a permanent place in your wardrobe, then buy the premium version later.
This approach gives you room to experiment without spending recklessly. It lets you push beyond your comfort zone while minimizing regret.
That’s exactly how I discovered I liked suede chukka boots. I picked up a cheap pair for around $10, and the more I wore them, the more I realized I genuinely wanted a high-quality version.
My Upgrade Order
If you want a general hierarchy for upgrading your wardrobe, this is the order I’d recommend:
Shoes
Shirts
Pants
Jackets
Shoes have the biggest visual impact because they anchor the entire outfit. Upgrading footwear instantly elevates almost everything else you wear.
Shirts come next because they’re one of the most noticeable parts of an outfit and are worn constantly.
Pants are more versatile and frequently worn than jackets, which gives them the edge for third place.
Jackets come last simply because most people wear them less often.
In terms of overall impact, I’d rank wardrobe upgrades like this:
Shoes → Shirts → Pants → Jackets
That order will give most people the biggest return on investment while building a wardrobe gradually and intentionally.
Best of luck upgrading your wardrobe, and let me know what you’d change about this approach.
Tags: style, upgrades