5 Timeless Vintage Essentials

By Connor Gressitt (@legarbaage

Vintage trends come and go. Kanye West wears a Harley shirt and its value skyrockets, time passes, and people forget. It wasn’t so long ago that low rise jeans were completely out, but with the rebirth of y2k styles, it seems like many garments are coming back from the dead.  

I remember in high school Members Only jackets were trending;  you were lucky to find one for fifty bucks at a vintage store. Now they sit on thrift racks and resale stores alike at twenty. Mine sits in the back of my closet, too full of memories to pass along. When I mentioned it to my Grandpa, he reminisced on their initial popularity boom in 1980. Time moves trends. 

Skinny jeans were seemingly the only option for much of the early 2000’s, but now you can’t give ‘em away; Carhartt Double Knees, Levi's Silvertabs, and JNCOs have taken their place. If you wait long enough, most trends die and come back around. In my experience, though, there are certain wardrobe staples that have never left the closets of the chronically well-dressed. For this article, I’ve chosen five timeless vintage essentials that I feel are gender-neutral and can be worn by  people of all experiences.

#1 Military Pants:

As long as there have been wars there have been military pants, and while the American war machine is responsible for an untold amount of suffering, its  greatest contribution to the American people has been  its surplus clothing. There are so many beautiful military pants from countries all over the world  in varying styles and colors, but arguably the most iconic pant style is the OG-107 Trouser. Made of 100% cotton, the fabric  name came from the military color code “Olive  Green 107” and was produced from 1952 to 1989. 

The pants feature two front pockets with slash openings and two back pockets with button flaps. Exterior pockets make for easy manufacture and easy access in combat or reaching for your wallet. The iconic high rise allows them to be worn near the belly button for a more dressy look, or comfortably down at the hips for a more contemporary casual vibe.  

Varying manufacturers and an incredibly long production run offers a wide variety of specifications; button fly, zip fly, waist adjustments, darker or lighter, thinner material or thicker material. And because they’ve been in circulation for so long you can find them practically deadstock, or totally  thrashed with authentic combat wear, stencils, and even original repairs. 

Their timeless roomy yet sharp fit, gentle color, and malleable shape makes them a flexible wardrobe staple that you can wear to work in dirty, party in hard, or even clean up for a first date. 

Signs I look for to determine the quality of OG-107 Trousers (these are not hard and fast rules, just loose guidelines):  

  • Original military tag: These usually have been removed or washed away over the years, but will help you determine the age of the garment if still present.
  • Hand Feel: This is a matter of personal preference, and what feels good to you is all that matters. 

#2 Vintage Blanks: 

Graphic tees are great, but sometimes you want something more subtle or neutral, something to balance an outfit and give room for a different statement piece to pop. Vintage Blanks fill this role. There are an infinite number of options in this department, from oh-so soft and thin fitted 50’s combed cotton blanks, to baggier thick 90’s blanks, to everything in between.  

I recommend having blanks in all the colors you frequently wear, but to stay in the world of OG-107 colors, my favorite pairings are Brown, Gray, or Black.  

I personally prefer a 100% cotton blank as I’m sensitive to synthetic fibers, but each person has their preference, and the only way to find out what you like is to experiment and try new things. Similarly, fit is a huge question in the blank world. I like a slightly oversized boxy fit most of the time, so something where the pit to pit measurement is close to the same as the shoulder to hem. Some folks like a more form-fitting blank tucked in, or a longer shirt to cover their belt. There’s also the question of pocket T or standard Blank.  

Try on some blanks and explore what is most complimentary to your body and personal style. 

Signs I look for to determine the quality of the blank (these are not hard and fast rules, just loose guidelines):  

  • A tag that reads, “Made in USA” 
  • Single stitching on the arms and or hem (in conjunction with a “Made  in USA” tag places it 90’s or earlier)
  • Hand feel 

#3 Cardigans: 

Everyone likes to be comfortable, and cardigans combine  maximum comfort with limitless layering options. Cardigans have been worn by movie stars, shop workers, Musicians (notably Kurt Cobain, who loved Mod Mohair Cardigans), and everyone in between. There are so many different cuts, materials, and colors, so I’ll stick to a few that I like best. 

My personal everyday cardigan is 90’s L.L. Bean woven cotton  cardigan in Grey. It’s slightly oversized and falls comfortably around my hips. With OG-107 Trousers I like to layer it over a shirt tucked in, but it  pairs just as easily with an untucked Tee. A cropped or more boxy cardigan is another favorite style of mine; especially for those who enjoy high waisted pants.  

I tend to wear a quieter single-color cardigan as a layering piece, but patterned or brightly colored cardigans are a classic statement piece for any wardrobe and are a slick way to peacock that isn’t as dreadfully on the nose as an allover print shirt. Yes, Mohair cardigans are extremely cool, but they are accordingly pricey; if you luck out and find one for the low, congratulations! Wear it with pride and harken back to sweet Kurt, but if not, a nice simple vintage cardigan will last a lifetime in your wardrobe.  

Cardigans of any style can be worn over a t-shirt, a flannel, or collared shirt and tie. They can be buttoned up if form fitting, or billowing wide open to create a larger draped silhouette.  

Cardigans from the 40’s to the 60’s were predominately wool or wool blends. In the 60’s we see lots of cool additions like mohair to the blends, and even suede and leather facings on the front. The late 60’s and into the 70’s we get a lot of  synthetics, namely acrylic, and it remained the dominant material in use throughout the 80’s. Cotton cardigans were around throughout all of these time periods, but in my experience are more rare. Each material offers a different balance of comfort and warmth to each wearer and again, the more you try on the more you’ll learn what you like.  

Signs I look for to determine the quality of a Cardigan: 

  • A quality brand tag. My favorites are Campus, McGregor, or Jantzen, but there are countless more, and really anything Made in USA is  probably solid. 
  • Material Makeup (this is a matter of preference, but in my opinion non synthetic materials are always a sign of quality)
  • Hand Feel

#4 Denim Jackets 

Perhaps the most iconic garment in American history, the denim  jacket will never go out of style. There are thousands of brands and  styles to choose from in this department, but I will simply list the three brands I like best and one style from each which I think is accessible to the average person.  

Levi’s is the dominant denim brand, and for good reason. Since the late 1800’s Levi Strauss & Co. has been manufacturing quality denim products for the working class consumer, and at each step of the way they have innovated iconic styles for all. They have made many jackets for many years, but the most timeless and certainly the most copied style is the Levi’s Type 3 Trucker Jacket. 

I personally love the look and shape of the Type 1 and 2 jackets,  but the Type 3 was the product of a great deal of experimentation and tinkering with an already successful design. The Type 3 brought the old workwear appeal of their earlier designs into the contemporary pop culture of the time. It debuted in the 60’s and really hit its stride in the 70’s with everyone from the working class to the artistic elite. The classic two-pocket style, which later came to be a four-pocket style in 1984, is more trim and flattering then their earlier models and fits better into the average wardrobe. The Trucker can be layered over literally anything; from shirtless to three piece suit, it’s probably been done, so  why not do it yourself? Personally I like a more oversized fit with my Levi’s trucker, which is much easier to find in 80’s and 90’s production models. I usually layer it over a flannel or cardigan to give the jacket a more filled-in full shape, but also often wear it right over a t-shirt for a more casual draped look.

Lee: the son in this holy trinity, Lee makes a damn good jacket.  Similar in style to the Levi’s Trucker, the Lee 101J is less popular but more affordable. If you like wearing something slightly different from everyone else around you, you might enjoy a Lee denim jacket. The zig zag stitching across the front placket is one of my favorite details, along with the slightly slanted breast pockets. To me, Lee reads true cowboy without the ubiquitous pretension of a Levi’s jacket.

Wrangler: usually last in people’s list of the great denim three, Wrangler gets a tough rap, but I think the placement of their jackets in Quentin Tarantino’s “Once Upon A Time In Hollywood” has brought their unique styles to our attention. Brad Pitt wears a 60’s Wrangler 24MJZ in the film, (Men’s Jacket Zippered, I’m assuming) which sports a total of four pockets and a zippered front with stitched pleats, which I like very much. These are quite rare and expensive, but wrangler continued to produce a similar style with a total of four pockets and rivet front that I think achieves the same look at a tenth of the price. It boasts a more fitted look out of the three presented, but is great if you like to wear more form-fitting clothes and pairs nicely with flares.

Signs of quality to look for with denim jackets: 

  • “Made in USA” somewhere on the tag
  • Wash or color of the denim (traditionally, the darker the wash means the less it’s been worn and thereby the more life you’ll get out of it, but a beautiful fade is also a treat).
  • Quality of the hardware (Rivets, zippers, etc.) Hand Feel

#5 Boots: 

Everybody needs a good pair of boots. Whether it’s for a long hike, a day of hard work, or just to dress up an outfit, boots are the most timeless and flexible shoe. Worn by working people for as long as we’ve had clothes, boots not only protect your feet and give you an inch or two of additional height, they also provide arch support, comfort, and style.  

In terms of quality and accessibility, the two best boot brands in my opinion are Red Wings and Doc Martens. Their many styles and flavors have been popular since their respective inceptions, and if you’ve ever owned a pair you know why. 

I’ll start with Red Wings. My favorite style and the pair that I wear more than any shoe in my closet are Iron Rangers. The pair I have are one of the only pairs of shoes I’ve bought new in the last 10 years, and they will likely be the last pair I ever have to buy. Red Wings are pricey, but you are investing in a shoe you could wear for the rest of your life.  

Founded in 1905, Red Wing Shoes is one of the last great American Heritage brands that continues to thrive solely (pun intended) on the quality of their products. Their boots pair naturally with workwear  outfits and true vintage styling, but I’ve been known to wear them with everything from OG-107 Trousers to a good skirt. There are a ton of styles and varieties of Red Wing Boots out there, and once you start looking, you’ll notice them more. Try on as many pairs as you can in  person to learn what style suits you best. 

Doc Martens are on the other side of the cool boot spectrum. European in origin, their styles have also been synonymous with the working class for as long as they’ve existed. But in contrast to Red Wing, their styles have adapted and changed significantly to keep up with the new styles of each generation.  

For me, their iconic 1460 style boot is the best. Again, it pairs with everything from a dress to work pants, but with a more contemporary flair. The yellow contrast stitching pops in a way that reads more hip and modern; Docs are the cool kid no matter how universally adopted and appreciated they are… which brings me to some closing thoughts.

Most of the garments I’ve mentioned in this article have been  popular for a long time and have been worn and styled by countless people. But just because “everyone” likes something doesn’t mean it isn’t cool. We each bring our own style and personal taste to each garment we own and outfit we assemble. An outfit of all vintage essentials might not be groundbreaking, but it gives you a foundation on which to find and build your own styling voice. 

If you’re new to vintage and are just starting to build your wardrobe, these are great pieces that you won’t have to cycle out and will inspire you to find more garments that express your individual taste and flair.  

Always seek out quality, and try to buy things that you can wear for a lifetime.

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