7 Classic Casual Clothing Items I’ve Had For 7 Years

classic casual clothing items for men

A single phrase I read on 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

classic casual clothing items for men levi's 501 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

classic casual clothing items for men 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

classic casual clothing items for men basic tee

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

classic casual clothing items for men clarks desert boot beeswax

Click Here For A Full Review

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.

classic casual clothing items for men clarks desert boot suede

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

classic casual clothing items for men red wing 877

Click Here For A Full Review

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

7 classic casual clothing items timex weekender blue nato

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.

7 classic casual clothing items timex weekender nato

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

classic casual clothing items for men belt

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.

Simple Design

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

classic casual clothing items Randolph Engineering Aviators

Click Here For a Full Review

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.

You Might Also Like


  • Reply
    August 29, 2017 at 11:07 am

    Dude, never commented on your blog before but have been reading for a bit. For an awesome leather belt, try out Galco. They’re fundamentally a gun leather and holster company, but I love their belts. I have a 1 1/4 inch in light brown. It’s lasted me 6 years and shows no sign of needing replacement. The buckles are interchangeable, but the one it comes standard with is classic brass.

  • Reply
    PJ Pires
    August 29, 2017 at 12:22 pm

    AWESOME AF, mate! It’s sad that Amazon don’t ship to Brazil.

  • Reply
    gary goins
    August 29, 2017 at 7:44 pm

    An excellent article. It is authentic and reflects you and I like your choices.

  • Reply
    August 29, 2017 at 11:55 pm

    Great article, Nate.
    If I go to a mall I see two hundred and fifty men who should read this.
    My first retail job, 45 years ago, was in a blue jean store which was a subsidiary of a men’s wear store. Not only did I get a fresh girl to date every week but a full style education and then some.
    Today I have 1- 3 pc black linen suit, 1- 3 pc black wool suit, 1 burgundy wool suit with pale blue and dark blue pinstripes giving almost unlimited options for different looks using color or not. 1 tuxedo. 30 silk ties. V-neck and crew neck sweaters in black and burgundy. V-neck and crew neck t-shirts in white for summer, black for winter, and, olive to match my eyes when I feel like it. Black jeans and blue jeans & 2 different types of shoes for different work. 2 different pair of black dress shoes; 1 laces and 1 slip on. 1 fall, winter, spring black leather coat 3/4 length with multi pockets. I ditched the liner and wear wool something underneath. Also the de-rigueur, silk scarves, sheepskin and or leather gloves. Also for winter; a flight jacket that can be paired with t-shirt hoodies (I have 7 in black), turtlenecks in black, white or olive, my silk underwear and/or merino wool soft as silk underwear, my merino heavy duty hoody, down coat, down vest, expedition coat with 23 pockets, wind and water resistant trousers, USN mickey mouse boots or mukluks and snowshoes. Also wool and leather mitts with the same wool glove liners in olive. Half a dozen different work gloves. A few other special occasion garments. All my clothes that touch the skin are 100% cotton, linen, wool, leather, silk except socks which I allow 15% synthetic. I also have maybe 20 hats for different uses and looks including berets, toques, bush hats and driving caps. A 4 ft closet and a 5 drawer dresser holds everything. I might buy new Magnum (Thermalite) boots this winter even at full retail because they were incredible but had to be trashed last spring after 5 yrs. Buying a 1/2 size bigger allowed me to wear them year round with sole inserts in the summer and woolen socks added in the winter.
    Yes, this all costs money but not nearly as much as some might think. Some things never go on sale but other things are seasonal and can be bought online off season for up to 80% off.
    If we learn to take care of our stuff it will take care of us and cost very little when amortized. Same goes for bedding and linens; sheets and towels are cotton or linen or wool. A Hudson bay blanket properly cared for can last your whole life. I never use the dry cleaner store. After wearing garments they are cleaned within the week and checked over. Spot cleaning for woolens or cold water by hand and seasonal a full wash in cold, water or warm or hot as allowed required. Missing buttons, loose threads, fallen cuffs are addressed right away.
    I should mention that hand sewing, including leather, has been a hobby since Boy Scouts and I can make any garment. Now I just do simple stuff on the machine which I just learned to do 2 years ago. It was easy; any guy can do it. Now, I just make stuff I can’t buy or stuff I can do better and cheaper.
    I have 3 watches that I wear regular. All are stainless steel, 2 are dress, one of those with a white face for day and the other with a black face for night. The third, Nate, is like yours though maybe a little higher end. Simple round case, three subsidiary dials, date at 04:00, two pushers, solid stainless with sapphire crystal. Made by Fiyta to commemorate the first manned Chinese space flight in 2003. 10,000 serial numbered. No, to the obvious question, they wisely purchased Japanese movements. I hated the band and got a King brand black patent leather for one. I got two others, the same watch, and did one with an olive band of the same color and material as you show but it is a flip over concealing strap with velcro closure. And the last has the same strap in black denier. One 8 mm handmade Kings chain for the neck and another 10 mm for the wrist. I also wear a tiny bottle on a black linen cord or slim silver chain with my ‘bitch killer’ potion in it. I love it when they ask what it is. Sometimes a handmade silver ring or two to compliment my chains. That’s about it.
    You got your style nailed, Nate, but very few men do. Women are just about as bad. They either overdo it or don’t do it at all.
    Keep up the great work!

    • Reply
      August 31, 2017 at 8:51 am

      Wow! I’m glad to see that you have your personal style nailed down and I appreciate the kind words from someone as established as yourself. I love how you have a mental inventory of everything you own, know how it all works together, and have a planned maintenance schedule. And you’re absolutely right about buying quality. You can buy junk over and over again or buy quality items and care for them properly and they’ll last for decades. Thanks for the contribution!

    • Reply
      November 19, 2017 at 8:03 am

      This gives me hope that I can eventually build a wardrobe that encompasses everything I need but nothing too extra. And can easily fit in my two tiny coat closets I have in my historical downtown house. Thank you sir this makes me happy.

  • Reply
    September 22, 2017 at 5:29 am

    Thank you Nate for sharing your personal style. I based most of my clothing to your style. Keep it up and looking forward for more.

  • Leave a Reply

    About Me

    Casual Style 101

    Free style guide