In-House Tailor - Chicago Showroom
About the job
- Previous experience in menswear alterations, including made-to-measure suiting.
- Expertise with industrial sewing machines used in alterations, including blind-stitch, serger, and straight-stitch machines, and industrial steam irons.
- Proficiency in hand-sewing and garment construction.
- A keen sense of color perception and fabric types.
- Strong time management and organizational skills.
- Comfort with iOS systems and Google Workspace.
- Ability to work calmly in a fast-paced environment.
- Ability to work with a team and maintain alteration quality standards.
- Interpersonal and communication skills to keep the showroom team up to date on standards and occasional changes.
- Professional appearance and manner that reflect the employer’s brand.
- Reliability and punctuality.
- A positive attitude and willingness to keep learning.
- Ability to collaborate with the showroom manager and client advisors to achieve good client fit outcomes.
- Pride in craftsmanship and attention to detail.
- Perform alterations on made-to-measure suiting, jackets, trousers, denim, and outerwear to the employer’s quality standards.
- Assist client advisors on the showroom floor with fittings, pinning, and advice on appropriate fixes for common fit issues.
- Apply guidance from the Manager of In-House Tailoring in the Chicago showroom to maintain consistency across showrooms.
- Keep the showroom team current on alteration standards and process changes.
- Manage the tailor shop’s workflow, turnaround times, and organization.
- Maintain equipment and keep the workspace clean and efficient.
- Experience managing a tailor shop or independent studio.
About the company
Proper Cloth makes made-to-order dress shirts tailored to each customer’s exact measurements and style preferences. It operates through an online platform where buyers design shirts by choosing fabrics, styles, and custom sizing, and the shirts are produced to order with a guaranteed perfect fit and about a two-week delivery time. The company differentiates itself by focusing on luxury quality, personalized service, and a straightforward online experience that delivers precise fit and high customer satisfaction. Its goal is to provide consistently perfect-fitting shirts that encourage repeat purchases in the premium apparel market.
Company Size
51-200
Company Stage
N/A
Total Funding
$150K
Headquarters
New York City, New York
Founded
2008
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Simplify's Take
What believers are saying
- Proper Cloth's August 2026 about page targets higher product quality and stronger branding.
- Fall ‘26 and Summer 2026 lookbooks show active merchandising and seasonal demand capture.
- June 2026 press from Esquire and the Wall Street Journal reinforces luxury menswear visibility.
What critics are saying
- Indochino and SuitSupply compress margins with broader assortment and heavier marketing.
- Showrooms in New York, Chicago, and Washington, D.C. raise fixed costs if traffic weakens.
- If AI sizing and fast-fashion tailoring improve, Proper Cloth's fit premium erodes quickly.
What makes Proper Cloth unique
- Proper Cloth combines online customization with Chicago and Washington, D.C. showrooms in 2026.
- Its Smart Sizes system, launched after 2010 customer polling, anchors fit personalization.
- The brand sells premium made-to-measure shirts with strong editorial credibility in 2026.
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Benefits
- Health Insurance
- Dental Insurance
- Vision Insurance
- Life Insurance
- Employee Discounts
- Hybrid Work Options
- 401(k) Company Match