Tailor

The Darien Sport Shop, founded in 1946, offers an exceptional shopping experience with three expansive floors featuring designer and contemporary clothing, accessories, gifts, and sporting equipment for all ages. Known for its outstanding customer service and unique in-store offerings, the shop provides professional alteration services by skilled tailors, free local delivery, and hosts special events like fashion previews and trunk shows.

As a family‑owned and locally‑operated business, it upholds a legacy of personalized service and active engagement in community and philanthropic initiatives.

We are looking for an experienced Tailor / Alterations Specialist to join the DSS team. In this role, you'll work alongside our sales staff to ensure every garment that leaves this store fits the customer perfectly. You'll handle alterations across menswear, womenswear, and outerwear — from simple hemming to structured suit tailoring — and you'll do it to the highest standard of quality and craftsmanship.

This position is available as either part‑time or full‑time depending on the right candidate. Whether you're a seasoned professional looking for a new home, a skilled tailor seeking the right environment to do your best work, or a newer tailor looking for some training and guidance, we want to hear from you.

• Perform alterations on a full range of garments including suits, sport coats, trousers, dresses, shirts, outerwear, and specialty items
• Partner with sales associates during fittings to understand each customer's preferences and needs
• Mark garments accurately for alterations during or following customer fittings
• Inspect all completed work before returning garments to ensure they meet DSS quality standards
• Operate and maintain all sewing and pressing equipment
• Keep the alterations workroom organized, clean, and running efficiently
• Communicate clearly with management on workload, timelines, and any garment concerns

• Demonstrated experience in a professional tailoring or alterations environment
• Proficiency in both basic and advanced alterations across menswear and womenswear
• Strong working knowledge of garment construction and a variety of fabric types
• Meticulous attention to detail — you hold your finished work to an uncompromising standard
• Ability to work independently and manage your own workload effectively
• Comfort working in a small, collaborative team environment
• Formal tailoring training or trade experience is a plus, but not required if your work speaks for itself
• Be part of an 80-year local institution with a genuine culture of craft and community
• Work alongside a close-knit team that takes pride in the work
• Handle high-quality garments from respected brands
• Flexible scheduling available; part‑time and full‑time candidates welcome
• Competitive hourly compensation commensurate with experience
• Employee discount on store merchandise
• A role with real ownership — your work directly shapes the customer experience
• Health benefits & 401k with 100% employer match up to 3% for full‑time employees