5 Vintage T-Shirt Styles That Are Still Popular

by John Amato

Vintage is a fancy word for “old.” Vintage clothing, therefore, is old clothing. Old looks or styles are great. 

Sorting through dusty thrift store racks, you might find the occasional gem … a sport coat that may have been salvaged from Cosmo Kramer’s wardrobe, or some bell bottom jeans that have been safely packed away since Woodstock.

However, it helps to remember that most old clothing was discarded for a reason.

Fortunately, the best vintage styles are still in production. This is especially true for t-shirts. There’s such an enormous demand for t-shirts that there’s always room in the market for maintaining all sorts of styles and prints from yesteryear.

At Jupmode, we make midwest-themed apparel and gifts, and we’re all about vintage looks.

Get the classic styles, without the holes and stains.

Let’s learn:

  • What is a vintage t-shirt?
  • Which vintage t-shirt styles still look great today
  • Where to find midwest-themed tees in vintage styles

What Is a Vintage T-Shirt?

Items are vintage if they are old and of enduring appeal.

How old exactly are vintage items?

There’s no precise agreed-upon definition, but items are typically considered vintage when they’re between 40–100 years old. Vintage-styled items are modern goods that imitate looks from those eras.

Here’s how vintage compares to antique items (which are older) and retro items (which are a bit younger).

Age Category Age Date Range Of Item Or Original Style
Antique 100+ years old 1922 and older
Vintage 40–100 years old 1922–1982
Retro 20–40 years old 1982–2002

Vintage styles are old enough to be definitively “not current,” but recent enough to be fresh in society’s collective memory. These are the styles that today’s old folks wore when they were young.

At Jupmode, we don’t sell vintage goods. But we do sell vintage styles—lots of them.

Our vintage prints and designs celebrate the looks and culture of the mid-20th century.

Here are a few of our favorite vintage t-shirt styles. You'll find these looks sprinkled throughout our inventory, combined with our original themes that honor the places and culture of the American Midwest.

1 - Vintage Logos and Cultural Throwbacks

gray and pink Rusty’s Jazz Cafe t-shirt

A shirt can capture a retro or vintage style by celebrating cultural history. Maybe it’s a moment in time, an iconic spot that’s closed down, or an old catchphrase that slipped out of fashion.

At Jupmode, we’re intimately connected to midwestern culture and we love to print designs that connect folks to happy memories.

For example, Toledo locals remember Rusty’s Jazz Cafe, where Margaret “Rusty” Monroe served up top-notch helpings of live music and spaghetti dinners.

”Love this shirt because of the quality but love it even more because of the memories my husband and I made at Rusty’s.”
— Danielle M., ★★★★★ Verified Jupmode T-Shirt Buyer

Here are a few more throwback prints that are uniquely midwestern and only found at Jupmode. 

green Toledo Sports Arena shirt

Toledo Sports Arena T-shirt


Michigan Is Super T-Shirt (Superman Ice Cream)


green Up North embroidered sweatshirt

Ay Ziggy Zoomba T-Shirt (Bowling Green State University)


2 - Tie-Dye T-Shirts

red and white tie-dye “Ohioan” t-shirt

Tie-dye is pretty old school. The art of tying up garments, applying dye, and unraveling to reveal splotchy patterns was popular in ancient Chinese dynasties as far back as the 5th century.

In the US, tie-dye is synonymous with the hippy culture of the 60s. Rock stars like Janis Joplin brought the style into the mainstream.

Colorful, mesmerizing tie-dye prints broke free from the straight lines and plain colors that came before.

While tie-dye is decidedly vintage, it’s never really gone out of style. It’s a beautiful aesthetic that’s established an enduring cultural foothold.


Find tie dye prints throughout the Jupmode catalog, like the tie-dye Ohioan shirt pictured above or this Toledo Rockets tie dye sweatshirt

3 - Crew Neck T-Shirts

red, white, and blue Lake Erie crew neck t-shirt

A crew neck shirt, sweater, or sweatshirt is one with no collar and a round neckline.

The crew neck design has become the t-shirt standard. However, it’s technically a vintage style that simply took over the market.

Crew neck tees were first manufactured in 1932 as undergarments. Over time, the style became acceptable as an outer layer.

The look was popularized by rower athletes, which is where the “crew” name originates.

At Jupmode, we offer lots of shirt designs, but most of our t-shirts are of the classic crew neck style.

”Love your shirts! They are so comfortable and bring back wonderful memories of growing up in Toledo.”
— Peter S., ★★★★★ Verified Jupmode T-Shirt Buyer

4 - Vintage Lettering Styles

gray and yellow vintage “Toledo” t-shirt

Vintage lettering is one of the most effective ways to communicate a sense of the past. We might not notice that the present day has its own set of lettering styles, but when we see certain old fonts we can instantly connect them to a time period.

For example, the TOLEDO print pictured above has a distinct 1950s feel. Meanwhile, this funky Ohio Skate Couple tee screams 1985, and the bubbly lettering on this Every Day Is Earth Day print is straight out of the summer of 1969.  

”Great company, great shirts… I live in Michigan and I buy the ones that mean something to me. Thanks, Jupmode!”
— Vickie, ★★★★★ Verified Jupmode T-Shirt Buyer

5 - Pocket Tees

green Midwest t-shirt with front chest pocket

You can’t beat the pocket tee for elegant simplicity. The chest pocket is a minimalist touch that turns a plain tee into … well, a slightly less plain tee.

”This shirt is one of the coziest I own and is constantly in rotation. I like the minimal design on the pocket and the color is great.”
— Nick, ★★★★★ Verified Jupmode T-Shirt Buyer

Pockets began appearing on t-shirts in the 50s as tees were becoming more commonplace as outerwear.

These uncomplicated shirts offered prime chest real estate for pockets. Rather than adding pockets on both sides, the left chest became the go-to pocket zone, creating a distinct, charming asymmetry.

T-shirt pockets were traditionally a place to hold pens and other small objects. Modern folks usually prefer to use pants pockets or a bag or purse for storage. The pocket is mostly just there for style points, but it’s still a nifty spot to keep a writing implement.

Today, you don’t see too many pocket tees, but it’s a smart look that’s basic enough to never truly be out of style. For a slightly nerdy top that’s one step above the completely plain tee, you can’t beat the pocket tee.

Here are a few more of our favorite pocket tee designs:

blue “I’m From Michigan” pocket t-shirt

I’m From Michigan Pocket T-shirt


black “Old West Ender” pocket t-shirt

Old West Ender Pocket T-Shirt


white “You Will Do Better In Toledo” long-sleeve t-shirt

You Will Do Better In Toledo Pocket Long-Sleeve T-Shirt


Get Classic Looks on New T-Shirts

For the best vintage t-shirt styles and midwestern-themed tees, shop Jupmode. We offer apparel and gifts for people who live in or love the American Midwest.

Visit one of our two retail locations in Toledo, Ohio, or peruse our entire inventory online.

We carry special collections for the following midwest places and institutions:

In each collection, you’ll find vintage looks, prints, and cultural throwbacks, all with a uniquely midwestern flavor.

For more buying guides and news, visit the Jupmode blog.

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