Premium Made to Measure Shirts Sydney

Custom made to measure shirts for professionals and weddings, designed and fitted in St Leonards, North Shore Sydney. Every shirt made to your exact measure.

Individual Approach

Every detail is tailored to your unique style, needs, and story, offering a truly bespoke experience.

Flawless Fit

Suits designed to feel as good as they look, with comfort, durability, and effortless elegance in every stitch.

In-House Expertise

All alterations are done personally to guarantee the perfect finish, because details matter.

Premium Made to Measure Shirts in Sydney – Built for Professionals

A premium made to measure shirt from Winslow Style is built entirely around your exact measurements – not adjusted from a standard pattern, but constructed specifically for your body from the first stitch. It is a shirt built around your exact body – your collar size, your sleeve length, your shoulder width, your posture – so that every time you put it on, it moves with you rather than against you. For professionals who wear a quality shirt five days a week, that difference is felt every single day. For the complete guide to made to measure business shirts – the Classic Five bundle, fabric differences, and pricing  read the complete business shirts guide.

At Winslow Style on Sydney’s North Shore, we make shirts for lawyers, finance professionals, executives and grooms who have reached the point where an off-the-rack shirt simply no longer makes sense. The collar gaps. The sleeves are too long or too short. The body is too loose across the chest or too tight across the shoulders. A made to measure shirt resolves all of that in a single consultation.

Every shirt starts with a full measurement session at our St Leonards studio. You choose the fabric – from quality cotton for everyday business to premium Egyptian cotton and fine weaves for special occasions – and every detail from collar style and cuff type to button choice is decided by you. Once your pattern is set, repeat orders are straightforward and your fit stays on file.

We make shirts for weddings, business wardrobes and special occasions. If you are dressing your entire wedding party, we can ensure every shirt is cut from the same cloth for perfect consistency across the group.

made-to-measure shirts

Let’s create an outfit that celebrates you.

17 years ago, I began tailoring not just to make clothing but to craft meaningful connections. Every stitch, curve, and fabric choice tells your story, designed with precision, care, and respect for your individuality.

For me, tailoring is deeply personal. I take the time to listen to your needs, understand your vision, and create something that mirrors your confidence and style. Your suit isn’t just clothing; it’s a reflection of who you are.

If you’re ready to step into something exceptional, I’d be honoured to create it with you.

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How will the process work

Book a visit

Book your made to measure shirts visit

Let’s start with a conversation about your needs and vision.

Collaborate on design Winslow

Collaborate on Design

We’ll work together to choose the style, fit, and fabric that suit you best.

Wear your perfect suit

Wear Your Perfect Suit​

Enjoy a suit that fits like no other, crafted to your exact measurements.

Get the best value for your budget

Our prices are tailored to your unique needs, ensuring you get the best value for your budget. Every detail, fabric, construction, and customisation can be adjusted to match your preferences. Let’s collaborate to create a suit that fits your style and budget perfectly.

$149

Classic Starter

A perfect entry-level option for those looking for quality cotton made to measure shirts, popular for business staples.

$199+

Groomsman Favourite

Perfectly tailored for all body shapes, for groomsman looking for the perfect fit.

$299+

Premium

An elevated option for professionals and discerning customers, featuring premium fabrics, extra handmade details and more attention to fit.

$499 - $699+

Bespoke

The pinnacle of luxury tailoring, the ideal option for creating your perfect first block, then repeat with our standard made-to-measure price points. Includes tuxedo shirts.

Material100% cottonEgyptian cotton 120/2Egyptian cotton 120/2 to 140/2Luxury brands' Egyptian cotton 140 - 200/2
ConstructionTailored shirts, made to fit from a standard block.Tailored shirts, made to fit from a standard block.Made to measure private tailor. More detailed fit, compared to a tailored fit.Unique Pattern Block - Multiple Fittings. Bespoke private tailor.
Fabric SelectionWide range of fabric optionsWide range of fabric optionsPremium fabric optionsPremium fabric options
CustomisationFull choice of customisation optionsFull choice of customisation optionsFull choice of customisation optionsFull choice of customisation options
Fit Guarantee100% Fit Guarantee - Lengths and Proportions100% Fit Guarantee - Lengths and Proportions100% Fit Guarantee100% Fit Guarantee
TimelineNormally 3-4 weeks. Rush orders available if neededNormally 3-4 weeks. Rush orders available if neededNormally 4-5 weeks. Rush orders available if neededNormally 8-10 weeks. Rush orders available if needed

Not sure which package to choose?

Visit us to explore fabric samples, customisation options, and expert advice tailored to your needs. We’ll help you make the perfect choice for your big day or special occasion.

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Frequently Asked Questions

Should I get a custom-made shirt?

A tailored fit is a game-changer! A made-to-measure shirt ensures a perfect fit that flatters your body type. At Winslow Style, we offer a personalised tailoring experience to create a shirt that fits well,  moves comfortably and showcases your confidence. While high-quality off-the-rack options exist, a custom shirt takes your wedding look to the next level

Planning is key! Allow yourself ample time for tailoring and adjustments. We recommend starting your search at least 6-8 weeks before the wedding. This ensures a stress-free experience and allows us to craft the perfect shirt for your special day.

A good wedding shirt should fit well, feel comfortable, and work with the rest of your outfit—especially the suit and tie. The fabric matters too. You want something breathable, smooth, and crisp enough to photograph well all day.

A custom shirt gives you control over the fit, fabric, collar, cuffs, and details. It’s not just about looking sharp—it’s about confidence, comfort, and having something made for you, not a size chart. For most grooms, it’s a small upgrade that makes a big difference on the day.

For a timeless and elegant look, cotton and linen blends are the top contenders with several weaves such as poplin, twill, oxford and sating finish are popular. 

Absolutely! We understand the importance of fit and coordinating your look with your groomsmen. We offer special deals for groomsmen’s shirts, ensuring a cohesive and stylish look for your wedding party.

Ready to order your perfect suit?

Book your free appointment today and step into the confidence of a perfectly tailored suit, crafted just for you.