Finest quality custom made to measure shirts in Sydney's North Shore.

Custom Tailored Shirts

Discover quality tailored shirts in Sydney's North Shore. Experience made-to-measure expertise for any body shape. Personalised fittings by an experienced designer with over 15 years of experience. Unlimited customisation options and premium fabrics available.


Luxury Custom Made Shirts

Welcome to our world of custom shirts. We’re genuinely proud of these beauties. They’re made from top-notch fabrics sourced from the best mills globally. Picture the comfort of premium Egyptian cotton! And the best part? You can customise everything from collars to cuffs to suit your style. Plus, we stand by our fit guarantee, so you can shop worry-free. Let’s find your perfect shirt today!

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Happy Customers

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Note that I have been a customer's of Ashan before (many years ago for my first suit), and it was an easy choice to choose him again for my wedding outfit! Ashan is a wonderful, kind and patient tailor. He has a great attention to detail, listens to exactly what we're after, and makes it happen! I had my wedding suit custom made. High waisted trousers, double breasted jacket, with an action back. All in a white creamy linen. It was to echo a 1940's vintage suit. There were several visits to Ashan, with the initial consultation, and then follow ups to measure, pick fabrics, lock in details, and he also adjusted some shirts for me, and we ended up with a custom spearpoint collar shirt.

Milton Lai

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Ashan was phenomenal. He was the consummate professional. Provided the right mix of advice and service. Ashan was on top of everything for the whole experience. I felt very in the loop the whole way and was able to design my wedding suit from scratch, right down the buttons and the cut of the shirt collar. The suit came out perfectly and I have had many comments since about the ensemble. I would not have any hesitations about referring Winslow tailoring.

Ryan Heighway

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Outstanding quality, wonderful service! I have had a bespoke suit and four shirts tailored by Winslow. I have just ordered three more shirts and another suit. Once you have a suit or shirt by Winslow you won't buy anywhere else. I am barrel chested – nothing fits me. I tried tailors in Sydney city, but they never quite fitted. I now have a fantastic suit that fits me like a glove and just love to wear. Ashan goes out of his way to help – I was fussy and changed my mind several times, but his superb level of customer service never wavered. And when time was tight, he went the extra mile to ensure I received my shirts before I headed a major conference. I'm delighted and cannot recommend Winslow enough.

Karl Maton

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Winslow Fashion Group is a leader in image consultancy, personal branding and quality made to measure clothing. Ashan is an artisan; knowledgeable and creative, taking a custom approach to whatever you need. He brings quality, style and convenience to the tailoring experience.

Mark Bilton

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Ashan is an absolute pleasure to deal with. From start to finish everything was great. My suit was fully customised and the advice he gave me on style was 100% on point. Do yourself a favour and book an appointment.

Alexander Donnolley

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Thank you to Ashan for your wonderful service in preparing a suit for a gift for my son Callum’s 18th birthday. Callum requested a suit in the Peaky Blinders style and Ashan was superb in helping find the authentic style and colour. I had no idea there were so many collar and cuff options! But Ashan was able to help Callum find the style and look he was after. Ashan’s friendly style ensured that the fitting was filled with laughter and cups of peppermint tea which made the whole experience enjoyable for my wife Marietta, Callum and myself. He kept in contact about the progress of the suit and was able to present it to Callum personally before an important job interview I will definitely be getting Ashan to make my next suit. Thank you Ashan!

David Ross


5.0 Rating on Google

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What We Create

Quality Made to Measure Shirts for any Occasion

Impeccable Quality

Indulge in the ultimate expression of sartorial elegance with our exceptional men's tailored shirts. Each garment is meticulously crafted using only the finest quality materials, including premium threads and buttons, interlining, and expertly calibrated stitching that achieves the perfect balance of stitches per inch and seam width.

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Luxury Fabrics

From the softest cotton to the breezy elegance of linen and the rugged charm of denim, our selection includes hundreds of premium fabrics from renowned mills such as Albini, Canclini, and many more

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Perfect Fit

Experience the epitome of luxury with our collection of made-to-measure bespoke shirts, where attention to detail and uncompromising craftsmanship are paramount. Indulge in the ultimate expression of sartorial elegance and elevate your style with our bespoke shirts that are tailored to your exact measurements.

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How it Works

Your Made to Measure Journey

Create your own masterpiece!

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Choose Your Style

Unleash Personal Style with Custom Shirts. Choose your Collar, Cuff, Plackett and other unique custom options.

Choose Your Fabric

Denim, Linen, Egyptian Cotton, and Beyond.

Get Measured

Get measured to achieve your desired fit, slim-fit, tailored-fit, relaxed fit or something in between.


Our beautiful custom shirts are delivered in 4-6 weeks from order date. We offer a 100% fit-guarantee.


Your unique pattern block is stored in file. Next time all your need to do is pick your style and fabrics.

Custom Tailored Shirts Pricing

Several options available to choose from

  • $299 - per shirt
  • $229 - 3+ Shirts
  • From $399

Business, Black-Tie and Luxury Casual Range

  • Egyptian Cotton, Linen
  • 2-Plyl
  • Wide Range of Fabrics and Colours
  • Quality Interlining
  • Fine Seams and Stich per Inch
  • 100% Fit Guarantee

Perfect for Groomsmen or Formals

  • Egyptian Cotton, Linen
  • 2-Plyl
  • Wide Range of Fabrics and Colours
  • Quality Interlining
  • Fine Seams and Stich per Inch
  • 100% Fit Guarantee

Special Order - Custom Design

  • Special request of unique style or fabric
  • Egyptian Cotton, Linen, Sea Island Cotton
  • 2-Plyl
  • Wide Range of Fabrics and Colours
  • Quality Interlining
  • Fine Seams and Stich per Inch
  • 100% Fit Guarantee

Have a special request in mind?

Whether it’s about design tweaks, specific fabrics, or pricing inquiries, we’re all ears! Drop us a message and let’s chat about how we can make it happen, just the way you like it.


The process is quite simple, first you will need to make a booking via the contact us form. The next step you visit our studio, where you get to touch and feel the actual product, see the quality of how it is made, and also choose the list of fabrics and customisation options. I will be able to guide you through the process, as I have been doing this for over 15 years and have a good sense of what fabrics works best for the different body types and style requirements. The final step is we gather your measurements and preferred fit, such as slim-fit, tailored-fit or classic-fit, these are made to measure shirts so you can choose the fit you like, and we will make it for you. It takes about 4-6 weeks, as we order fabrics from mills in Europe and get them made. Within 6 weeks you will get to fit your shirt, and it comes with a 100% fit guarantee, which means we will make it exactly to the measurements and style you requested.

We can definitely help you, we have fitted clients with all body shapes, if you are tall, short, wide or skinny; made to measure shirts are the way to go. We have had many times customers that have had different arm lengths or very particular requirements where it is impossible to find something in stores, we are able to help. If you have a question, just pop it in the contact us form and we will contact you. Any question is a good question, we are here to help.

We only source from reputable and ethical mills, and we only purchase quality Egyptian Cotton or Sea Island Cotton fabrics. You will feel the difference when you put them on, especially if you are wearing the shirt for a long time, you will notice what quality actually feels like. All our threads, buttons, fusing, and accessories that are used to make the shirts are of the highest quality, we do not skimp on quality. So what you get is exceptional value.

Our made to measure shirts are usually around the $299 price point. When you buy in bulk there is a saving as we are able to save on freight charges and we forward all savings to you. To really understand our shirts you need to come and see the quality, it is something we are really proud of and can stand firmly that we are one of the best in the market.

The measurement process is done only the first time we meet, and we do an extensive fitting to make sure we get the best desired fit, once we have done your measurements once, we will never have to do the measurements again. All you need to do to re-order is send us an email, or come to our studio and choose the shirt fabrics and style options. If you are to loose weight or put on weight, then we will need to take the measurements again, but note that there is no charge to get your measurements if you are ordering from us. If you are ready to order your custom, tailored made to measure shirt, then simply complete the booking form and your availability and we will call you to confirm a booking time.

Our standard turnaround time for a made to measure shirt is 4-6 weeks, but we do have exceptions and have been able to achieve the result in 3 weeks. It all depends on fabric availability and time to ship, we pre-order our core range fabrics and keep in stock, so if the item is in stock we can get it to you in 3 weeks. Let us know what you are looking for and when, I can let you know if this is a realistic date by looking at our stock and resource availability. Our made to measure shirts are made with two techniques machine and handmade, with excellent attention to detail. All shirts come with a fit guarantee, which means you will get the fit that you want.

Our made to measure shorts are made with exceptional care and quality and we stand by our quality and give you a 100% guarantee on our product. The fit, the construction and the materials are of the highest quality. If you are not happy with our quality when you receive the garment on our fitting, we will give you a 100% refund. If you are not happy with the fit, any minor adjustments are done free of charge if needed, and we offer you a 100% fit guarantee. It is a made to measure shirt and the perfect fit is given and we stand by our product.

Contact Us

We are here to help!

    Call for Consultation

    0447 474 777