High Sport Case Study: 5 Anti-Lessons For DTC Brands


High Sport Case Study: Ditching "Best Practices" To Transform $860 Pants Into A Must-Have Item

A few weeks ago I shared my POV on why fashion brands should NOT pursue the luxury strategy. In this issue, I’m going to share an exception that proves the rule.

High Sport is a brand that seems to have come out of nowhere, taking the shopping recs newsletter-verse by storm with their $860 knit pants. That’s right: $860. Knit pants.

Before we get into it, I want to thank this week's sponsor: Segments Analytics.

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The brand’s founder Alyssa Zacharay did an interview with Puck’s Lauren Sherman this year and shared the brand’s brilliant go to market strategy. She basically took the DTC fashion playbook and slam-dunked it into the trash.

Here are 5 counter-intuitive lessons from High Sport’s success. Apply these selectively to your brand (or not!).

#1 Don’t “Move Fast And Break Things”

The Standard DTC Playbook: spin up a “minimum viable” iteration of your first product idea ASAP, then use Meta Ads to validate the idea. Use consumer feedback from those orders to refine the product over time.

High Sport’s Approach: spend more than a decade on market immersion and product development before shipping a single product.

Alyssa Zacharay developed the initial idea for High Sport almost a decade before the brand sold its first pair of Kick Flare pants.

Like most fashion founders, she saw white space in the market–clothing that was as polished as traditional RTW, as versatile as an LBD, but as comfortable as athleisure.


Tons of brands have traversed these waters, but most have failed to do justice to all three goals. Zacharay spent more than 3 years on fabric development, working with mills to perfect the fiber blend and weave that would do justice to her vision.


Unlike many DTC-first founders, she possessed deep experience in design and product development–decades of experience as a merchandiser at The Row and Khaite. She knew what sold well for the specific customer she had in mind.

You could say that High Sport has been in development for decades, from the moment Zacharay started her career in fashion.

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#2 “The Most Expensive X” Is Almost Always Strong Positioning

The Standard DTC Playbook: try to undercut the competition on pricing or optimize price:value ratio.

High Sport’s Approach: redefine the top of the market.


Before High Sport launched there were “designer leggings”, but AURs typically topped out around $500-600. At the high end of the market you were paying for a logo, not quality. And the available options were strictly anchored in the gym.


There were also “designer pants” with AURs that exceeded $1,000 but again–consumers were paying for a logo. Designer RTW brands didn’t go all-in on engineering the most functional pant with the best fit.


The white space in the market? Pants that were both polished and functional. They took the “jeans that feel like a legging!” remit that plays so well in Middle America (for a reason!) and made it palatable for the elite.

Redefining the top of the market is almost never a bad idea. You just need the positioning and product feature development to back it up. Just ask La Mer, Dyson and Louboutin Beauty.

#3 Use Boutiques As A GTM Strategy

The Standard DTC Playbook: Use an eCommerce site and Meta Ads as your GTM strategy.

High Sport’s Approach: The brand launched in just three boutiques: A’maree’s in Newport Beach, Calf., Just One Eye in Los Angeles and Nuages in Aspen.


Zachary knew from her experience as a merchandiser that these boutiques catered to her target core customer. The boutiques’ owners had a direct relationship with many of their highest-spending clients, so they could provide product feedback in close to real time.

The upsides of this approach:

  • The only major financial outlay was inventory production.
  • The boutique owners’ enthusiasm for the product was its own validation mechanism.
  • It allowed the brand to reach an audience that is typically too niche to target profitably on Meta.


Of course, Zachary was able to get High Sport stocked in these boutiques because she presumably had a decade+ working relationship with their buyers and owners. YMMV.

#4 Don’t Get Your Hands Dirty With Marketing

The Standard DTC Playbook: The brand owns marketing, and performance marketing is one of the brand’s biggest expenses.

High Sport’s Approach: Move in silence, and let your wholesale accounts do the marketing. High Sport leggings took off in the fashion newsletter/influencer affiliate community for two reasons:

  1. The brand’s wholesale accounts like Net-A-Porter offer fat affiliate commissions and a gifting program to select influencers.
  2. The brand’s GTM strategy and Zacharay’s industry bona fides reinforced High Sport’s reputation as a “high status brand”.


If you’re getting free Kick Flares, and you’re getting 40% of the sale of each pair of $860 Kick Flares, and possessing the Kick Flares signals that you are high status…it’s a no brainer to post.

BTW, these are the hidden mechanics behind a lot of brands that multiple folks in the “status” fashion influencer community all start to talk about simultaneously.

#5 Use eCom As A Demand Capture Channel

The Standard DTC Playbook: eCom is the primary channel. Meta Ads are used to capture in-market demand, and those shoppers convert online within 7 days of seeing an ad. Wholesale is used to build awareness (if at all).


High Sport’s Approach: High Sport launched its business in 2021, but didn’t launch its own eCommerce site until May 2024–nearly three years later.


For the majority of that first three years in business, the brand’s Kick Flares were almost impossible to order on demand. You had to sign up for a waitlist with one of their stockists and/or wait for a restock to drop.


Many of the brand’s core styles are available to order on demand on its eCom site, but new launches like gingham are sold out in many sizes.


Basically, instead of attempting to conjure demand from scratch, High Sport is using eCom as a vehicle for tapping pockets of existing demand that has been building up since the brand launched.


As far as I know they’re still not running any paid marketing directly. Cash flow must be popping.

113 Cherry St #92768, Seattle, WA 98104-2205
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