A single phrase I read on Styleforum.net has had more impact on my personal style than anything else I've read or heard. It went something like…
If you can take a photo of yourself in black and white and it's difficult to tell which decade you're in, your clothing is most likely timeless.
Such a simple statement has made a huge impact on the way I think about clothing and it's stuck with me ever since.
When I first accumulated a collection of casual clothing that was authentically me, I used to joke that this was going to be my go-to look until I was an old man.
Well, I'm going on 7 years and I've adopted basically the same thing as my personal uniform.
Many of the pieces are featured in my free 10 Timeless Wardrobe Essentials eBook and this way of thinking is the basis for my foolproof beginner's style system, Casual Style 101 – The Affordable Wardrobe Guide.
7 Classic Casual Clothing Items I've Had For 7 Years
Not only am I wearing the same basic casual style that I was years ago, in most cases, the exact same pieces I bought in 2010 have lasted this long with regular use.
That's the benefit of buying quality over quantity.
Dark Denim – Levi's Shrink-to-Fit
I've always been enamored with patina on everything from boots to furniture to carpentry tools. And as I pointed out in my 4 Part Raw Denim Series, it was denim fades that initially drew me to upgrading my casual clothing.
My first pair, which I'll never throw out, is the classic Levi's Shrink-to-Fit. These jeans are denim-done-the-old-way.
Shrink-to-Fit simply means that they aren't pre-shrunk, so you have to size up to achieve the desired fit (about 1” in the waist and 2”-3” in length).
The best part about the Levi's Shrink to Fit 501 is that you can get a pair of raw jeans that are extremely durable and classically styled and cut for around $50.
Simple Sneakers – Converse Chuck Taylor
I first bought my Converse Chuck Taylor sneakers to wear to the gym for squats and deadlifts, but they were so comfortable and classic looking that they soon migrated into my causal wardrobe.
I started wearing them with jeans in the fall and spring, sockless with shorts in the summer, and even while woking around the house and painting.
I'm cheating a little with this list because I'm actually on my second pair, but the style is exactly the same and my first pair in the photo above lasted almost 6 years with daily wear!
Plain Fitted T-Shirts – Mossimo Supply Co
When I was searching for fitted T-shirts years ago, they were almost impossible to find. Most brands were wider than they were long, which was a real pain in the ass for me since I'm 6'2” and was about 165 lbs at the time.
But luckily I stumbled upon on the basic tee from Mossimo Supply Co and it fit perfectly. I bought one, wore it, washed it and wore it again.
Thanks to the cotton/poly blend it didn't shrink noticeably in the dryer, so I bought one in every color I could find and eventually picked up a spare in my favorite colors.
Most of these have been worn about once every week or two for workouts, undershirts, or my only shirt for the past 7 years and only now am I needing to demote them to purely workout shirts, as the deodorant stains have permanently darkened the underarms.
Chukkas – Clarks Desert Boot
Chukka boots are some of the most versatile footwear you can own and the Clarks Desert Boot is a great representation of the category.
They're more on the casual end of the spectrum so keep in mind that other brands may be better if you plan on wearing them in a business environment.
But they make excellent daily wear shoes for students and business casual guys.
For my first pair, I opted for the beeswax leather which develops a great patina in a short amount of time and wear them with jeans, chinos, and textured dress pants and they look great with all.
My second pair of the Clarks Desert Boot are a sand-colored suede and they add a warm element to cold weather looks while also honoring the “desert” name in the summer.
Rugged Boots – Red Wing 877
With style and durability to last a lifetime, I felt the Red Wing 877 was the perfect choice for my first pair of casual rugged boots.
I've had many jobs that required me to wear steel-toe work boots, so I'm used a little weight and stiffness, but these Red Wings were torture when new!
Most modern work boots have padded synthetic interiors so the break-in period is almost nonexistent, but the 877 is tough leather inside and out.
At first, these boots were the most uncomfortable thing I'd ever put on my feet. But with a few wears, the moisture from my feet helped soften the leather and the pressure from walking and bending helped massage the leather into a custom fit.
Now, they're extremely comfortable! I've worn them on 3-day camping trips, only removing to sleep, without developing a single blister.
The Red Wing 877 looks best with jeans, but can be dressed up a little with heavy patterned suiting material and elements of workwear. Think Gentleman Hunter when trying to dress these up.
Versatile Watch – Timex Weekender
My first watch that wasn't made of plastic and rubber was my Timex Weekender.
I love the chronograph style, and I can change its personality with a simple band swap.
I wear my Timex Weekender with jeans and boots, chinos and a sweater, and a suit and tie.
I've had to change the battery once and am due for another one soon, but other than that, it's worked flawlessly for 7 years. Not bad for $50.
Note: Had I known anything about watches at the time, I would've probably gone with a Seiko 5 for its automatic movement at the same price point. I don't think there's a better overall value on the market.
Brown Leather Belt – Unknown Maker
Just after buying my Levi's Shrink-to-Fit jeans, I went in search of a wide leather belt to match the rugged aesthetic of the jeans.
I found this belt at a thrift store for a few dollars and have worn it with every pair of jeans I've had over the years.
Despite being old when I got it, it's held up really well and I expect to have it for years to come.
This is the closest match I could find. While I can't vouch for the brand, the reviews are good and it looks nearly identical to mine.
What makes these pieces classic?
They feel authentic
The main reason these clothing items have stayed in my regular rotation is because they make me feel like me.
I've tried many styles over the years but keep coming back to what I feel comfortable in and that just so happens to be jeans, boots, and simple shirts.
Sure I like to dress up when the occasion calls for it, but that isn't practical for my day to day.
The quickest way to have a closet full of clothes with nothing to wear is to chase trends.
Trendy clothing becomes dated very quickly and is too noticeable to be worn frequently.
However, when you buy clothing with simple styling and classic inspiration, you can wear the items multiple times per week without anyone noticing and without having to worry about a style expiration date.
The only reason you'll have to get rid of basic clothing items is if you outgrow them or they get trashed from frequent wear.
They get better with age
Six out of seven items on this list look better today than they did seven years ago.
This could've been a seven out of seven, but dark armpits on your t-shirt is never a good look. But absent that flaw, a little fading and fraying on a tee doesn't detract from its casual image.
To illustrate the importance well worn clothing consider the fact that I wouldn't trade my Red Wings for 10 brand new pairs of the same boots because an authentic patina is worth so much more than a new product.
I even think my watch looks great with its micro scratches, frayed nylon, and worn leather bands.
Bonus – Future Classics!
I have a couple other timeless clothing items that see a ton of wear, are built to last, and always get attention.
However, they didn't make the list because I've only had them for about 4 years.
I still think they're great pieces for you to have in your wardrobe so I'll include them as a bonus.
Leather Jacket – Guess
I can't wear this jacket in public or post an Instagram photo without answering at least a few questions about it.
It's a classic cafe racer style and the color and texture of the leather make it look like a million bucks.
Unfortunately, Guess doesn't offer jackets of this quality anymore so if I were to buy another today, I'd go with the Mission Leather Jacket from Schott NYC, the most reputable leather jacket brand out there.
Aviator Sunglasses – Randolph Engineering
Not only is the Randolph Engineering Aviator styled to outlast trends, they're built to last even longer.
They're available with scratch resistant and drop tested glass lenses, the 23k gold plated frames are super flexible, and the welds are strong and nearly invisible.
They are a bit heavy, but I've never handled a pair of sunglasses that felt this robust.
Now It's Your Turn
If improving your personal style is high on your list of priorities, you can get started today.
Feel free to copy my style exactly, pick and choose the items you like, or simply let the philosophy guide you in creating a completely different look.
The choice is yours.
All the best,
P.S. If you like the ideas in this article but need a little more guidance, pick up your copy of Casual Style 101 which will walk you through the entire process.