Chicago, New York and the very serious business of buying menswear

Yes, I am fully aware that flying overseas to beautiful cities, eating at great restaurants and buying clothes for Calexico Man sounds like a fairly questionable definition of “work”. But someone has to do it.

This time, our Calexico Men’s Director, Kalem McCarthy, and I headed to Chicago for The Collective, one of the biggest menswear fairs in the world, followed by a slightly unexpected detour to New York. It was our first buying trip together and, after six nights, two cities, countless appointments, a few late nights, several very good meals and one Anna Wintour sighting, I can confirm two things: we found some incredible new brands for Calexico Man, and Kalem can definitely keep up.

Chicago first

We based ourselves at The Hoxton in the West Loop, which was exactly where we wanted to be. I love The Hoxton in Paris, and Chicago has the same formula down pat: great interiors, a lively bar, excellent people watching and enough happening downstairs to make “just one drink” slightly dangerous on a buying trip.

Chicago in summer was such a great surprise. Lollapalooza was on at the same time, so the city was heaving, but the energy was fantastic. Those extra hours of daylight also had me questioning, once again, why Queensland refuses to participate in daylight saving.

The weather, however, had absolutely no idea what it was doing. One day hot, the next thunderstorms and flash flooding. Kalem and I ambitiously attempted a run through the city one morning and were very quickly reminded who was in charge. Luckily, my trainer back home, God love him, had prepared gym sessions for us, which we both actually did. We work hard; we play hard. Balance.

The Collective

The real reason we were there was The Collective. Buying a season is one of my favourite parts of the business, but after 18 years of doing it, I also know how disciplined you have to be. You see hundreds of brands and thousands of pieces, millions of swatches, and eventually everything starts to blur into a sea of beautiful linen shirts, denim washes and very persuasive sales agents.

Our job is to edit.

We went in knowing the designers we wanted to see but also scoured the fair looking for what we didn’t know we needed yet. Some brands made the cut, some didn’t. That is buying.

I was really proud watching Kalem work through it all. He stayed focused, asked questions, learnt and took the time to understand how I approach a buy after nearly two decades of doing this. And having previously worked in Canada with Flight Centre, he also turned out to be possibly the most useful buying companion I have ever travelled with. Essentially, I had my own Men’s Director and personal travel agent with me at all times.

We found brilliant new denim, beautiful summer shirting, accessories, a ridiculously good party shirt brand out of Tokyo and several new designers I cannot wait for you to see.

There may also have been Bloody Mary’s provided by AG Jeans on the Sunday morning, an instant pick-me-up when you have stayed out a little later than planned and your body still thinks it is somewhere over the Pacific. My motto, which Hannah Walker can absolutely vouch for, is that I don’t do hangovers and I don’t do jet lag. It’s all in your mind.

Eating our way around Chicago

Obviously, one cannot buy menswear on an empty stomach. We ate incredibly well, including Momotaro, a partner dinner with Orlebar Brown at Le Colonial which was very fun, and Tzuco with Avant Toi, which was one of my favourite meals of the trip.

We spent a few hours in Wicker Park, which gave me serious Chapel Street in Melbourne back-when-Chapel-Street-was-a-vibe energy. While we were there, we stopped at Antique Taco and I had possibly the best shrimp taco of my life. A large statement, but I stand by it.

Shop Kalem's Chicago edit here!

Another night took us to Gemini near Lincoln Park, where the peppers, rosé and atmosphere somehow became one of those simple dinners you remember long after the trip.

We also managed a proper pub crawl, live music at Lucky Bird, 90s covers at The Pearl Club and a late-night nightcap at Richard’s. Research, obviously.

We took the search for coffee just as seriously and eventually discovered Foxtrot, where I managed to find a very decent oat cortado. Crisis averted.

And then New York called

We had finished what we came to Chicago to do when one of our favourite designers invited us to New York. Technically, New York was not on the itinerary, but when you are already on the other side of the world and Manhattan is only around two hours away, it almost feels irresponsible not to go.

At least that is what we told ourselves.

We were very generously put up at 11 Howard, and suddenly the buying trip had a second chapter. Our first night started with dinner at The Noortwyck, followed by one of those quintessentially New York moments you couldn’t plan if you tried: I spotted Anna Wintour casually walking alone down Bleecker Street.

Although “walking” might be underselling it. It was more of a very determined strut.

We continued the night at Employees Only for drinks, a little boogie and chats with locals. If Kimmy is working, find her. Even the arrival of a steak tartare at your table somehow becomes pure theatre.

Ten hours on the buying train

The following morning, it was straight back to work. We spent roughly ten hours moving between appointments, seeing familiar faces, meeting new designers and looking at what is coming for Spring Summer 27.

The highlight for me was Avant Toi. I have loved this brand for years and the new collection is exceptional. The colours, textures and fabrication are exactly what I want Calexico and Calexico Man to be showing next summer, and I am so excited about what we selected.

I also discovered the most incredible new accessories line, which I am deliberately not going to tell you too much about yet.

Kalem had his own major find too: a seriously cool men’s jewellery brand, family run and around 60 years in the business, that has somehow never made its way to Australia. Until now. We are incredibly excited to be the first to bring it here.

Watch this space.

One last New York night

Our final night became one of those great New York evenings where old friends, new friends and people who just happen to be in town all collide.

One of those new friends was Eric Wilson, former New York Times fashion writer and someone who has seen plenty from inside the fashion industry. Let’s just say dinner came with some excellent stories.

Eric and his partner took us to Cookshop, right near their apartment, and it was exactly what you want from a neighbourhood New York restaurant: great service, beautiful farm-to-table food and a buzzy Manhattan atmosphere.

Afterwards, Kalem and I decided sleep was probably overrated and met friends at Raoul’s. If you know, you know. A tiny, late-night French bistro filled with the sort of people who look as though they definitely know something you don’t.

It was the perfect way to finish the trip before beginning the considerably less glamorous 24-hour voyage home.

What is coming home?

This is the part I love most. A buying trip is not about finding more. It is about finding better.

Better denim. Better shirts. Better fabrication. Better accessories. Brands with a story and pieces that feel different.

The Calexico Man customer has changed too. He isn’t necessarily buying a wardrobe dictated by an office anymore. He dresses for travel, dinners, weekends, milestones, long lunches and days off with family and friends. He wants to look good without looking like he has been told what to wear.

He can wear whatever the hell he wants, whenever he wants.

From the next denim shape to brilliant Japanese party shirts, beautiful summer shirting, Italian knitwear, accessories and some seriously good new jewellery, we came home feeling incredibly clear about where Calexico Man is going next.

It was six nights away from my three babes Lenny, Joe and Gus, which felt strangely long. At three, Gus still has an uncanny ability to find his way into Jamie’s and my bed in the middle of the night, usually taking up approximately the same amount of space as a fully grown adult. You think you want uninterrupted sleep until suddenly you are on the other side of the world and miss having a small foot wedged into your ribs at 3am.

Shop Kalem's Chicago edit here!

So yes, it is a pretty cool job. I get to fly to Chicago and New York, eat at wonderful restaurants, discover new designers and, occasionally, buy beautiful clothes that I fully intend for my husband to wear.

But the real privilege is bringing it all home.

Watch out Australia. Calexico Man has some very good things coming.

Nicky xx