Alexander Jackson Fashions in the Field 2025 Boxing Day Interview

Drawing on his background in menswear styling and his work with Jackson Made to Measure Suiting, Alexander Jackson took out the 3 Wise Men menswear prize at Fashions in the Field on Boxing Day 2025 at Ellerslie. His win secured him a place at the prestigious The Ned Prix de Fashion 2026, set to take place on Saturday 7 March, where the country’s most accomplished race-day dressers will compete on Champions Day.

In the lead-in to the big event, Alexander reflects on the moment of his win, the philosophy behind dressing well, and what it takes to craft a competition-ready race-day outfit for New Zealand’s high profile racewear event.

Congratulations on your win at the Boxing Day races, what was going through your mind when your name was announced?

I was somewhat expecting to win, since I’ve got experience dressing men of all walks of life and am constantly improving my own style drawing on helpful knowledge from wherever I can. That said, even the favoured bet can still lose so it was a bit nerve racking up to the point: part of the fun, right?

Tell us about your winning outfit – how would you describe the look and what inspired your race-day style this year?

The outfit was inspired by the season of summer. So, I used colours similar to what you would see out and about: dry, earthy tones and brighter colours like orange and blue.

How long did it take to plan and pull the outfit together? Did you work with any particular brands, tailors, or stylists to achieve the final look?

I run Jackson Made to Measure Suiting in downtown Auckland: by appointment only. My personal wardrobe comprises pieces that fit well and to my style. Putting the outfit together took me like five minutes. Planning out a sustainable and stylish wardrobe, though, is a continual effort.

What was the key piece that anchored the whole outfit?

Probably it was the suit. It’s made from brownish-orange wool that is spun and woven at a heavy weight specifically to aid ventilation whilst retaining a firm drape. It uses minimally sized shoulder pads, less sleeve wadding and light canvassing so the silhouette is quite relaxed. Exposed on the inside the brownish-red medallion Italian lining is quarter lined for even more breathability and in conjunction with the horn buttons help to create design elements that all complement each other.

How important is fit and tailoring when dressing for a menswear competition like this?

It’s paramount: though it can be tricky for men to get something that fits well. There’s a lot of choice, a lot of different price points, and a lot of marketing out there. It’s part of the reason I started Jackson Made to Measure, you don’t pay for the marketing, the pricing is transparent, and the choices you get to make are more considered and informed.

What do you think caught the judges’ attention about your look?

I could imagine separating out placement involves considering both the whole outfit and every individual detail. For me details must be done well and the overall outfit has to be coherent. So having those two things happening at the same time.

What do you enjoy most about race day at Ellerslie?

The grounds itself, having quite a history, still brings people together. We were all manicured and well-groomed on the day, but the racecourse couldn’t be beat; never have I seen such immaculate greenery.

Winning the menswear section sponsored by 3 Wise Men comes with a prize – have you redeemed your voucher yet? If not, what pieces are you hoping to put it toward?

My wardrobe is too full: and am endlessly editing down. I redeemed it for my visiting brother from Australia, and it was right down his alley. The team at Newmarket were very helpful.

What advice would you give other men thinking about entering racewear competitions?

I think more than knowing how to dress is knowing why you should dress well is most important. Do you want to communicate to your loved ones a sense of dignity? To exercise a healthy level of creativity? Make people feel more comfortable talking to you? It can be as deep or not as you like but nonetheless it’s really important to have to know.

Will we see you back competing again at Ellerslie?

Perhaps. Hopefully, it’ll be men I’ve suited.