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Tis’ The Season To Get Engaged!
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  • The Pro’s and Con’s of getting engaged during the festive season
  • Top 3 Tips on Sorting Out the Outfits for Men
  • Article Conclusion

Engagement season is actually a thing, global statistics prove that the period between November and February has the highest spikes in couples getting engaged.

It makes a lot of sense as during this period is when most of the people are winding out their work projects leading into Christmas, people tend to take extended holidays and the overall mood is quite positive, making it the ideal time to ask the big question.

From the twinkling lights on the Christmas tree to the dangling mistletoe and all the eggnog, wine and family laughter.

Christmas is a time of the year to celebrate with your loved ones, and if you’ve been together a while, the chances are you’ll be spending Christmas Day together. It is a season where romance is in the air.

We have done some research and guess what? If you are deciding to pop the question this festive season, you are not alone. The following are the top 5 most popular days globally to get engaged, ranked in order.

  1. Christmas Day
  2. Valentines Day
  3. Christmas Eve
  4. New Years Day
  5. New Years Eve



Extra Vacation Time

Getting engaged in the holiday season means that you will always be able to celebrate in style this special moment with the love of your life. Whisking them away on a romantic getaway will always be possible during the holiday period with all that extra vacation time.

It’s Memorable

In 20 years time if you are sitting over dinner with friends and family and someone decides to put you on the spot, and question you on your engagement date to see if you remember when the proposal happened, you can be confident that you won’t make a fool of yourself. This is an easy date to remember.

Backdrop of Romance

If you decide to pop the question in the holiday season, you can be confident that the background and the setting will provide the romantic vibe that you desire.

The twinkling Christmas lights on the streets or the New Year’s Eve fireworks display will ensure that you will have no shortage of spots to pop the questions.  Not only will the day be special, but the setting will always be remembered through the photos and videos that you capture on the night.


It Is Predictable

The idea of proposing during the holiday and festive seasons may sound good, but in theory, a ring for the holidays is predictable. Be original and make your engagement a surprise. Pick some time when she really won’t expect it and make it memorable.

It Will Cost You A Fortune

Getting engaged during the peak retail, Christmas and engagements season will cost you a fortune, all vendors maximize sales opportunities and profits during this peak season.  Not only that they will be expensive, but some vendors such as caters could be fully booked well ahead during this season.

Your Anniversary Will Always Compete

It might sound incredibly romantic for now, but in years to come your anniversary will be overshadowed by another event.

Once you have popped the question the next few months have a lot of planning and preparation for the wedding, this is an exciting time and one that can be stressful without the right resources and support.

Many couples engage professional planners, wedding styling services, and custom menswear and womenswear designers.

As the groom, you have few duties that you will need to check off your checklist which is typically in your control.
Choose your best man and groomsmen
Organise your outfits.

Conventionally your brother trumps your best friend as best man, but the ultimate call is yours. In the modern wedding, traditions can be somewhat overlooked and do what your gut tells you and make you most comfortable.

It really does not matter, it is your day and do what makes you feel the best. But you will need to make the decision sooner than later so that you can start to delegate.

Photo by Gabriel Crismariu on Unsplash

Top 3 Tips on Sorting Out the Outfits:

Get The Look

Getting the look that reflects the theme of the wedding, and consistent with the groomsmen and bridesmaids is not an easy task. If styling is not your forte, then we suggest you best hire someone that has the experience and skillset of styling menswear for weddings. The idea here is to visually balance the wedding parties to complement each other and highlight the bride & groom.

Making Sure the Look Fits Every Body Shape in your grooms’ party

Making sure that what you have finally decided is available and fits every body shape is the greatest challenge that all grooms will eventually find.

We have experienced this with several of our clients that have shopped in retailers and have found the look they want, just to notice few weeks before the wedding when all of the groomsmen have had the time to connect and try on the suits, that not every brand is designed for all body shapes.

We understand that most couples are time poor, and hence we offer an obligation free home service, where we come to you and complete the whole process at the comfort and convenience of your home.

When do I start looking for the grooms and groomsmen outfits?

Start sourcing the look at least six months before the wedding day and the process of making and organising the making of the suits 3 months prior to your wedding day.

Leave the final touch up alterations to 1 month to your wedding day, this will make sure your suits are adjusted to suit your most up to date weight.


If you are looking to pop the big question this season, firstly we would like to wish you all the best, make it special, and make it personal and unique.

And when the time comes for you to start looking for the grooms and groomsmen outfits, feel free to contact us for a home visit obligation free. We would love the opportunity to create something beautiful for your wedding.

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Ashan Winslow

Ashan Winslow, the man behind Winslow Style – knows what it takes to be a leader in the menswear style industry. His passion is to create bespoke and made to measure menswear clothing be it an event to attend or refreshing your closet.

He is an experienced image consultant in Sydney to provide a personalised one to one service at the convenience of your office or home. Winslow Style works with customers from all walks of life, from the power real estate broker and the corporate executive to the entrepreneur looking for a new look or the groom who wants to attend his wedding in a perfectly tailored suit.

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