Advertising Creative Director

  • New York, New York, United States
  • Full-time
  • Marketing
  • $80-120k

About Proper Cloth

Proper Cloth is a leader in the direct-to-consumer men’s custom clothing market.  Our vision is to build a leading, global, luxury menswear brand.

We see a future where people don’t buy clothes in sizes that don’t fit or styles they don’t love.  A future where perfect, custom fit clothing is made on-demand for a superior customer experience and a more efficient supply chain.

Some quick stats about us: 

  • 52 employees (January 2020)
  • Headquartered in Soho, New York
  • Over 200,000 customers worldwide
  • Over $20m annual revenue 
  • Profitable, not venture backed

There aren’t many businesses like ours.  We’re half fashion brand and half tech-startup.  We've been called “Our New Favorite Online Custom Shirtmaker” by GQ magazine and “One of the most successful made-to-measure e-commerce sites” by Esquire.  We’re profitable and growing fast.  We’re committed to building something that lasts.  


Position: Advertising Creative Director

We’re seeking a creative leader capable of taking Proper Cloth’s marketying and advertising creative direction to the next level.  This role will collaborate with our paid advertising team to conceive, produce and optimize brand building, response driving campaigns.  In this role you’ll be joining a passionate, talented team of creatives and working directly with the CEO.


  1. Creative - able to generate new ideas and build on other people’s ideas
  2. Analytical - comfortable analyzing data for patterns and insights
  3. Excellent Communicator - with excellent copywriting skills and a passion for story-telling
  4. Excellent Taste - in visuals and design, with a strong portfolio
  5. Humble - open to being wrong and letting the best ideas rise to the top
  6. Proficient in the Adobe Suite
  7. Deep understanding of the affluent, luxury customer
  8. Familiar with the current menswear market and leading brands
  9. Experience working with direct-to-consumer brands
  10. Has high standards, values hard work and is results-driven


  • Develop new concepts for advertising campaigns
  • Produce mockups, and provide direction for digital and print campaigns
  • Produce storyboards for video campaigns
  • Produce scripts for video, radio and podcast campaigns
  • Produce copy, and provide copy direction for ads and landing pages
  • Art-direct video and photography production
  • Coordinate with marketing, product, and engineering teams to launch new campaigns
  • Collaborate with advertising and data teams to maintain and optimize campaign performance
  • Think through and optimize the entire on-site customer journey, from landing page to product page to email marketing to eventual purchase



More About Marketing & Advertising at Proper Cloth

The Team

Our marketing and advertising team is driven by a group of nine designers, photographers and copywriters - and closely tied to new product development, web design, merchandising and data analytics.  


Brand Values

As a brand, our marketing seeks to project the following values: 

  • Attention to Detail
  • Reaching Ones Potential
  • Earned Success
  • Technology Enabled
  • Quiet Confidence
  • Approachable


Our Marketing Approach

We believe that building a brand and driving a response from the customer are not mutually exclusive activities.  They go together and support each other.  It can be a fine line to walk, but it’s critical for long term success.  Marketing encompasses a variety of efforts at Proper Cloth, but three in particular are worth highlighting: 

1. Tell Our Product’s Stories

We take great pride in our products: the materials, the design, and the craftsmanship, and a big part of our marketing is explaining what makes these products special.  We’re trying to help the customer appreciate the products for what they are and make better buying decisions.  

  • Email Marketing, Product Pages, Category Landing Pages.

2. Produce Lookbooks and Fashion Campaigns

Great design and quality are critical, but clothing purchases are also driven by how well a brand resonates with a person’s personal identity.  With this in mind, we go through a great effort to produce exciting images, videos and lookbooks that exhibit the Proper Cloth lifestyle and communicate more emotional brand values like adventure and ambition.   

  • Lookbooks, Style Guides, Advertising Campaigns, Email Marketing, Home Page Design, Social Media.

3. Paid Advertising

Our paid advertising is almost entirely focused on new customer acquisition with the practical message that “Proper Cloth makes it easy to get perfect fitting custom shirts”.  We run paid campaigns across a wide range of online and offline channels.  The key to our approach is to experimentation.  We’re always trying new concepts, channels, creative, copy, and landing pages - and measuring everything.  We’re incredibly data driven, continuously evaluating conversion rates and customer acquisition costs to optimize campaigns. 

  • Facebook, Google, SiriusXM, Podcasts, Mailers, Magazines, Influencers.


The Challenge

Driving consistent, double digit growth, in a way that is profitable and not brand dilutive is incredibly challenging.  It requires finding the careful balance between brand and response driven creative, between aspirational and relatable positioning, and between explainer and emotional content.  

It requires thinking through the entire customer journey, from their first exposure to Proper Cloth, to helping them understanding what we do, to building them the confidence to make their first purchase.  

And in a fast moving organization, it requires careful communication and coordination between multiple people and parties, including product development, web design, copywriting, photography, social media, merchandising and more. 


The Opportunity

At Proper Cloth, we believe we have an opportunity to create the next great luxury menswear brand — a unique brand with a more efficient supply chain, and a superior customer experience, all driven by custom, made-to-order products.  

Today we’re the largest men’s custom shirtmaker in the world, but we’re still a small player in the overall menswear and luxury markets.  In 2020 we’ll be expanding beyond shirts into new categories and opening additional physical showrooms. 

With our unique expertise in technology and engineering, you’ll be joining a marketing team that already has a powerful, data-driven infrastructure.  Come help us improve our marketing and create a menswear brand that lasts for decades to come. 

Apply Now