What Should a Premium T-Shirt Cost? The Business Case for Charging More… and Why We Are Not

Pricing a T-shirt should be simple. Calculate what it costs to make, add enough margin to run a healthy business, and set the price. In theory, there is little more to discuss.

In practice, pricing has become one of the longest-running debates between the two founders of IF... THEN WELL. We have returned to it for six years. Sometimes because our costs increased. Sometimes because a retailer insisted on higher margins. Sometimes because we looked at the premium T-shirt market and worried that our lower price made our quality easier to underestimate.

Two recent events brought the debate back with more urgency. Imports from Peru are now subject to an additional 12.5% U.S. tariff, applied regardless of factory certification or labor standards. We also lost our only retail partner because our pricing left less room for margin than higher-priced competitors

Both developments strengthened the argument for raising our price. In fact, when the debate is limited to business logic, there is a clear winner. The case for charging more is stronger.

The reason we have chosen not to is more personal…

When Quality Meets the Reality of Cost

We started IF... THEN WELL in 2020 because we could not find the everyday T-shirt we wanted. We were looking for the rare combination of comfort, quality and versatility: a T-shirt soft enough to enjoy wearing every day, durable enough to support that kind of use, and refined enough to work just as easily with jeans as under a jacket. Just as important, we wanted to know that once we found the right one, it would still be available in the same form years later - something dependable enough to become a true staple rather than another favorite that eventually disappeared or changed.

We found the material in Peruvian Pima cotton. Its long-staple fibers help create a fabric that is soft, breathable, durable, and resistant to pilling. We refined the fit and focused on details that many people may never consciously notice. The neckline uses a narrow double-stitched construction that hides the seam normally visible where the collar joins near the shoulder. This allows the shoulder seam to be angled slightly forward to improve the way the shirt drapes.

That quality is expensive before construction even begins. Peruvian Pima cotton grows in a limited range of suitable climates and is traditionally harvested by hand to help protect its extra-long fibers. The construction details we insist on also limit the factories capable of making the shirt to our standards. Even so, our goal was never to create the most expensive T-shirt we could justify, but one exceptional enough for everyday wear and priced to be worn that way.

Our current single-shirt price is $37. Three shirts cost $100, and larger bundles reduce the price per shirt further. Those are the prices a customer sees, but they reveal very little about what remains after a sale.

The difference between a retail price and the direct cost of making a product is not take-home profit. Freight, tariffs, packaging, payment fees, warehousing, photography, marketing, customer service and dozens of other overhead expenses must be paid before a company earns a true profit. A price can appear healthy from the outside while leaving surprisingly little room to operate and grow.

Six years in, the business is coming off its best sales year and is on pace to grow another 20% in 2026, yet it still does not generate enough profit for either co-founder draw a salary.

We have created a product we believe in, maintained a return rate below 5% (virtually unheard of for online apparel) and seen roughly half of our first-time customers return to buy from us again. Those numbers tell us the product and the idea behind the company are working. What we have not yet built is a business with enough financial strength to invest consistently in its own growth.

That reality cannot be dismissed as greed. Profit allows a company to reach new customers, maintain inventory, provide better service, and absorb an unexpected tariff without lowering its standards. It gives a small business room to make long-term decisions instead of constantly reacting to the next expense.

The Business Case for Raising the Price

A higher price would immediately improve the economics of every direct sale. If we sold the same number of shirts, we would have more money to reinvest in the business without adding another product, finding more customers, or compromising the shirt itself.

That additional margin could support marketing, social media, inventory, content, customer service, and the many other things a growing brand needs. It could help us remain in stock more consistently and introduce the product to men who would value it but have never heard of us.

There is also reason to believe that our core customer may be less price-sensitive than we first assumed. A customer searching for the least expensive T-shirt has countless options below our price. The man who chooses a men’s Pima cotton T-shirt from a small Miami company is usually looking for something else. He cares about comfort, fit, construction, versatility, and the convenience of owning fewer pieces that work more often.

Our customers also buy without being trained to wait for a promotion. We intentionally avoid constant sales, countdown clocks, and endless discount codes. Our men’s T-shirt bundle offers permanent savings because ordering several shirts creates real efficiencies. It is not a temporary incentive designed to pressure someone into buying immediately.

This suggests that many customers are choosing us for quality and simplicity rather than because we are the lowest-priced option. A thoughtful increase might not drive those customers away. It could instead give us the resources to serve them better.

Price also communicates quality before the product has a chance to do so. A customer shopping online cannot immediately feel the cotton, inspect the stitching, or see how the shirt falls on his body. He sees the photographs, the brand, and the price. Consumer research has found a positive relationship between price and perceived quality, particularly when buyers have limited information with which to judge a product.

That does not mean expensive products are automatically better. They are not. It means, however, that customers often use price as a shortcut until they have better evidence.

At $37, our shirt looks expensive beside a mass-produced $15 tee. At the same time, it can look suspiciously inexpensive beside another men’s premium T-shirt selling around $100. One established premium label, for example, currently sells a comparable extra-long-staple cotton T-shirt for $98.

We are confident saying that our Tee meets, if not exceeds, the same standard of quality. The material, construction, fit, and finishing justify that comparison. Yet the higher-priced shirt is more likely to be recognized immediately as “premium,” before the customer has touched either product or examined how each one is made.

That is the power of price positioning. A customer may see the $98 T-shirt and assume quality. He may see our $37 shirt and ask what is missing.

Nothing is missing. But our price asks us to prove that, while the higher price allows the other product to begin with the assumption.

Raising our price could place us more clearly in the premium tier, reduce that uncertainty, and give us more money to explain what makes the shirt different. It might reduce demand among some customers, but it could also make us more credible to another group. In premium clothing, price acts as both a cost and a signal.

From a conventional business perspective, moving to $70 (or even $98) is not a reckless idea. It is a sensible one.

What Being Dumped Taught Us

From the beginning, IF... THEN WELL was built around selling directly to customers. Avoiding the traditional retail middleman was one of the ways we hoped to make a premium Peruvian Pima cotton T-shirt available at a price that still made sense for everyday wear.

Even so, we saw value in being represented selectively in smaller, high-end men's boutiques. The goal was not to build a wholesale business. We wanted more men to discover the shirt in person, where they could feel the fabric, try on the fit and compare the construction for themselves. We also valued the chance to hear real-life reactions and testimonials from customers encountering the product outside our own website.

Through personal relationships, that eventually led to our T-shirts being carried by a local high-end men's boutique. We were willing to make that relationship work on terms that would make very little sense in a traditional wholesale model. In effect, we were prepared to give up nearly our entire margin because we viewed the store less as a profit center and more as an opportunity for exposure, discovery and firsthand customer feedback.

Even that was not enough.

The reason is fairly simple. High-end retail depends on larger dollar margins than our current pricing allows. A retailer may sell a premium T-shirt for $100 and keep roughly $60 of that sale before paying rent, employees, insurance, utilities, inventory costs and the rest of the expenses required to run the store. That $60 in gross profit gives the retailer room to operate.

A $37 T-shirt simply cannot create the same economics.

Even if we were willing to surrender almost everything we would normally earn on the sale, the retailer would still be left comparing a much smaller dollar margin against competing products that may sell for $100, $150 or more. Shelf space, inventory dollars and employee attention are limited. From the retailer's perspective, the comparison is not only about which T-shirt is better. It is also about which one contributes enough to support the business.

From the retailer’s perspective, simply marking the shirt up from our online price is not a viable answer. Doing so risks undermining trust: if a customer discovers that the same T-shirt costs dramatically less from the brand directly, he may start questioning what other hidden mark-ups exist throughout the store. For a high-end boutique, that reputational risk can outweigh the benefit of carrying the product.

That experience taught us something important. Our pricing was not merely inconvenient for wholesale. It was fundamentally out of step with the economics of the high-end men's apparel world we were trying to enter.

To participate meaningfully in that market, a brand generally needs to leave enough room for the retailer to earn a substantial margin while still preserving some margin for itself. At our current price, there is simply not enough room for both. A higher retail price would change that calculation and make wholesale partnerships possible without asking either side to work for almost nothing.

That is part of what makes the business case for raising our price so difficult to dismiss. A higher price would improve the economics of direct sales, create room for wholesale, strengthen our premium positioning and provide more money to invest in growth. The new tariff adds still more pressure to a model that was already tight.

The spreadsheet is not confused. It says to raise the price.

The Price Has to Match the Purpose

The argument against raising our price begins with a different question. What is this T-shirt supposed to do?

Our answer has always been that it should make everyday life a little simpler. A dependable T-shirt can become the cornerstone of a capsule wardrobe because it removes choices rather than creating them. It works on its own, under a sweater, or beneath a jacket. It can be dressed up or down. When the fit and feel are right, a man can own several and stop spending time searching for replacements.

That idea depends on repetition. A useful everyday product should be priced so the customer can actually use it every day. It should not feel so precious that it stays folded in a drawer while a cheaper shirt handles ordinary life.

This is why our bundles are central to the brand rather than an afterthought. If a T-shirt is designed to be worn often, it makes sense to own more than one. Three shirts for $100, with lower per-shirt pricing on larger bundles, helps customers build a reliable rotation around a product intended for everyday use.

The pricing also reflects how our own costs behave. When several T-shirts are purchased together, fixed expenses such as packaging, fulfillment, shipping and marketing are spread across more units, lowering our cost per shirt. Rather than manufacturing urgency through occasional promotions, we make the savings permanent and visible.

A higher single-shirt price would make the bundle structure harder to preserve. At some point, even with meaningful savings, the bundle would no longer serve the original purpose: making it practical to build a dependable rotation around the same T-shirt.

The price would also begin changing the story of the brand. For six years, we have written about buying fewer, better things. We have discussed capsule wardrobes, decision fatigue, timeless style, predictable pricing, fewer promotional emails, and the value of resisting impulse purchases. We have argued that quality should remove friction from life, not display status.

A large price increase would require more than editing a product page. It would ask us to reconsider the philosophy running through nearly every part of the company.

We could move further into exclusivity. We could make the packaging more elaborate, create artificial scarcity, or use the higher price as evidence that the shirt belongs in a luxury category. Those strategies might work. They simply are not the work we set out to do.

The Decision a Spreadsheet Cannot Make

We understand that value ultimately belongs to the customer. If someone buys a $95 T-shirt, understands what he is purchasing, and feels satisfied, that transaction is not dishonest. Different companies have different labor costs, distribution models, manufacturing volumes, marketing expenses, and histories. A higher price alone is not evidence that a company is taking advantage of anyone.

We also understand that IF... THEN WELL must earn enough to survive. A business that refuses to acknowledge arithmetic does not protect its principles for long. It simply disappears.

Our disagreement is not about whether we are allowed to earn a healthy profit. It is about whether we should increase the price primarily because branding and customer psychology might allow us to do so. It is about the difference between charging what is necessary to make the product well and charging what the premium market has been trained to accept.

One of us keeps returning to a personal test. Knowing everything we know about the shirt, its construction, its quality, and the market around it, would we willingly pay the proposed price ourselves? Not once as a novelty or gift, but repeatedly, as the foundation of an everyday wardrobe.

If the honest answer is no, asking our customers to pay it feels wrong for this company.

That is not the strongest argument on a spreadsheet. The business case favors the founder who wants to raise the price. Higher margins would help us grow. A higher price might improve how customers perceive the product. It would give retailers a reason to carry us and help absorb new costs such as the recently introduced tariff.

Yet we did not start IF... THEN WELL merely to discover the highest price the market would tolerate. We started it to build a company we would want to be customers of ourselves. That means making an excellent product, providing thoughtful service through policies such as “Make Sure It Fits,” and setting a price we can defend after the branding and emotion are removed.

Our price may eventually need to change. Manufacturing, freight, tariffs, and other costs do not remain still. If an increase becomes necessary to preserve the product and operate the company responsibly, refusing to act would not be principled. It would be denial.

What we will not do is raise the price simply to create a more exclusive image. We will not use price as a substitute for quality, and we will not knowingly sell an everyday product at a price we would personally refuse to pay.

For us, the right price must support both the product and the customer. It should be high enough to protect our quality standards, give us the resources to stand behind what we sell, and build a healthy company… but not higher simply because the premium market has shown that someone will pay it.

The business argument says we should raise the price. Our founding philosophy asks whether we would still be proud to stand on the customer’s side of the transaction.

For now, that question carries more weight.

 

SOURCES:

Office of the United States Trade Representative (July 28, 2026) – Notice of Actions in Section 301 Investigations of Acts, Policies, and Practices of Various Economies Related to the Failure of Each Economy to Impose and Effectively Enforce a Prohibition on the Importation of Goods Produced with Forced Labor

Journal of Marketing Research (August 1989) – The Effect of Price, Brand Name, and Store Name on Buyers’ Perceptions of Product Quality: An Integrative Review