Tailored to Perfection: Personalised Men's Alterations in North Shore Suburbs.
Proudly offering high-quality alterations in Crows Nest, North Sydney, Mosman, Willoughby, St. Leonards and surrounding suburbs. Book now!


Men's Tailoring

We offer a personalised men’s alteration service, by appointment, at our studio at St. Leonards. Our studio offers private fittings where we provide quality guidance on achieving the perfect fit. If you are looking for an alteration service to guide you in re-creating your outfit, please contact me. I would love to help! 

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Happy Customers

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We simply cannot recommend Winslow Tailoring enough. After spending years and thousands of dollars on suits that never quite fit, we reached out to Ashan for a custom made ensemble of a suit and two shirts for our wedding. The whole experience was second to none. From the moment we met, we knew we were in good hands. His is knowledge is superb, the selection abundant and his all-round aura just beaming - you can tell Ashan loves what he does! We had choices of things we didn't even know were optional! Like the style of watch you wear and how it sits on your wrist, or the size of the collar. The list goes on .... And the finished product?! Well, what can I say - James Bond worthy. Just WOW! So Happy, actually couldn't be happier! Oh, and we've already returned to have designer tees and jeans altered - which were finished in record time so we could take them away with us. Thank you so much! Very happy customers.


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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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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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I ordered a wedding suit through Ashan and it was an excellent experience and great outcome. He was very generous and flexible with his time, from taking measurements to follow up alterations. Ashan offered great guidance through the process too which made everything easier. Highly recommend!

Chandan Hegde

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Ashan is a superb suit tailor with a true passion for formal wear and fashion. I am able to wear my suit with pride to my event on incredibly short notice all thanks to Ashan's hard work

Silas Shambly

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Ashan was absolutely fantastic. He gave me some great advise and direction when deciding on the suits (I had no experience when it came to styles/material/colours and he was able to guide me through), he went above and beyond meeting with us for fittings and made a group of guys in every shape and size look amazing on my wedding day. Very much appreciated! (I'm the one in the grey vest - my best man thought he should be the centre of attention)

Mark Judge

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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


5.0 Rating on Google

A personalised alteration experience

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Common Frequently
Asked Questions

On average, men's alterations typically take around 1 week to complete across the industry, but things like shortening pants or taking in the waist should usually take around a few days to complete, or sometimes same day. The rule of thumb is allow a week for most things and you should be fine.

“When should I have my groomsmen fitted? "Groom and Groomsmen alterations are usually best left as close to the wedding day as possible; this ensures that your guys do not gain or lose too much weight before the actual wedding day. Usually about 2-3 weeks before the wedding day is fine, but always confirm with the tailor to check their availability a few weeks before that.

When it comes to shirt alterations, there are a few easy fixes that can make a big difference. If the sides are too loose, a tailor can take them in for a more fitted look. Additionally, adding darts can give a shirt a more flattering silhouette. For sleeve alterations, a tailor can easily shorten or lengthen sleeves to achieve the desired fit. So, whether you need a shirt taken in or let out, or sleeves shortened or lengthened, a tailor can help you achieve the perfect fit.

Yes, you can shorten the length of your men's suit jacket. It is recommended to consult with a professional tailor who specializes in men's alterations. The maximum length that can be shortened depends on the specific design and construction of the jacket, as well as your personal preferences. Generally, the maximum shortening for a suit jacket is around 1-2 inches from its original length. However, it is crucial to have an experienced tailor examine the jacket and provide precise measurements to ensure the alteration is done correctly and maintains the overall balance and proportions of the garment.

When it comes to shortening or lengthening the pants, the quality of work from the tailor or seamstress determines the value for what you pay. The average pants alteration cost in Sydney ranges between $15 to $30. We charge $25 and it is a premium quality job by an experienced tailor, having it tailored is worth it, as it will definitely uplift the outfit.

Pricing is best quoted by looking at the job that is needed to be completed. If you have any questions simply drop me a message via the website or text me on 0447 474 777 and I will reply within 24hrs.


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