In-House Tailor - Chicago Showroom

In-House Tailor - Chicago Showroom (Full-Time)

Proper Cloth · Chicago, United States · Full-time · Posted 2026-10-22

Salary: USD 62,000–62,000

Workplace: on_site

Department: Product/Design

Description

About Proper Cloth

Proper Cloth is one of the most respected names in premium menswear, with showrooms in three states and more on the way. We’re a values-driven company built on craftsmanship, great fit, and exceptional client service, and we offer real opportunities to grow with us. 

The Role

We’re looking for a Full Time In-House Tailor to work in our Chicago Showroom’s tailor shop. As an in-house tailor, you will provide an extra level of service to our customers by providing necessary alterations that will give our clients their best fits in jackets, trousers, casual pants, denim, and outerwear. We strive to deliver an extraordinary shopping experience, and as an in-house tailor you will be instrumental in accomplishing this goal.  We're a small team and the right person has the potential to make a big difference. 

What You’ll Do:

• Perform alterations on made-to-measure suiting, jackets, trousers, denim, and outerwear to Proper Cloth’s quality standards
• Assist client advisors on the showroom floor with fittings, pinning, and advice on the best fixes for common fit issues
• Put guidance from the Manager of In-House Tailoring into practice in Chicago so all our showrooms stay consistent
• Keep the showroom team current on alteration standards and any process changes
• Manage the tailor shop’s workflow, turnaround times, and organization
• Maintain equipment and keep the workspace clean and efficient

Requirements

• Previous experience in menswear alterations, including made-to-measure suiting
• Experience managing a tailor shop or independent studio is a strong plus
• Expertise with industrial sewing machines used in alterations, including blind-stitch, serger, straight-stitch machines, and industrial steam irons
• Proficient in hand-sewing and garment construction, while maintaining an open mind when presented with new ways to execute various alterations 
• A keen sense of color perception and fabric types
• Strong time management and organizational skills
• Comfort with iOS systems and Google Workspace 
• A calm, composed demeanor in a fast-paced environment
• Ability to work with a team and ensure Proper Cloth’s promise of excellence is maintained in all alterations
• Well-developed interpersonal and communication skills as this will be imperative while getting the showroom team up to date on standards and occasional changes
• A professional appearance and manner that reflects the Proper Cloth brand

Who you are:

• Reliable, punctual, and someone your team can count on
• Positive, friendly, and eager to keep learning 
• A natural collaborator who works well with the showroom manager and client advisors to get every client the best fit
• Proud of your craft and committed to getting every detail right
• A great leader who can work with the showroom manager and client advisors to ensure our clients get the best fit possible
• Excited to learn everything there is to know about menswear and Proper Cloth!

Benefits

• Generous custom clothing allowance!
• Employee discount on items beyond clothing allowance
• Free lunches & snacks
• Salaried at $62,000/year
• Full health benefits, medical, dental vision, life
• 401(k) with match after one year of employment 
• Access to One Medical Membership

Apply

Apply at Proper Cloth

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