Chosen by Tuchuzy deconstructed linen pant in white, styled for a Paddington shopping day

Paddington and Woollahra: A Shopping and Long Lunch Guide

Bondi is where we live and where the shop has stood since 1995. But there is a second rhythm to the Eastern Suburbs, ten minutes inland and a world away from the sand, and it belongs to Paddington and Woollahra.

Where Bondi is salt, terry towelling and the walk back from the water with wet hair, Paddington is terraces, plane trees, and the long lunch that starts at one and does not resolve. It is the other half of how women here actually dress: the day you put on proper shoes.

This is our guide to spending a Saturday in it.

Start at Five Ways

Begin at Five Ways, the junction where Glenmore Road meets Broughton and Heeley and the streets all fold in on each other. It is the most Paddington thing in Paddington: a pub on the corner, terraces stacked up the hill, and no obvious logic to any of it.

Come early. The point of starting here is that the streets around Five Ways are for walking, not for arriving. Glenmore Road bends and climbs and the terraces get progressively more beautiful, and if you have only ever driven through Paddington on Oxford Street you have essentially never been.

Wear something you can cover ground in. This is a walking morning, and the hills are real.

Work your way down to Oxford Street

Oxford Street is the spine, and it has had several lives. Some of it is quiet now and some of it has been reborn, and the honest truth is that the pleasure of it is in the drift rather than a checklist. The boutiques are worth going into slowly. The good ones here, like the good ones in Bondi, are the ones where someone actually chose everything on the rack.

If it is a Saturday, the Paddington Markets are running in the grounds on Oxford Street, and they are still one of the best places in Sydney to find something nobody else will be wearing. Emerging labels, jewellery, ceramics, the occasional excellent vintage stall. Go with an open head rather than a shopping list.

What to wear for this stretch: something that works standing up, walking, and being looked at, which is exactly what a good linen trouser does. The Deconstructed Linen Pant from Chosen by Tuchuzy pants with a scoop tank is the uniform, and it is a uniform because it works. Add a real sunglass from our sunglasses wall, because Oxford Street in the middle of the day is bright and unforgiving.

The long lunch

This is the actual reason people come to Paddington on a Saturday, and everyone knows it.

The move is to book somewhere at one, sit outside if the weather allows, and let the afternoon do what it wants. Paddington rewards the unhurried. Nobody here is rushing back to anywhere. It is one of the few pockets of Sydney where sitting at a table for three hours is not just tolerated but slightly expected.

Dress for the table, which means the top half matters more than you think. A good tank, a strong neckline, gold at the ear. Something from tanks and tees under a blazer is the most useful thing you can do to a lunch outfit, because Paddington in the shade is meaningfully colder than Paddington in the sun and the blazer will be on and off all afternoon.

Then up to Queen Street, Woollahra

Woollahra is the calmer, more assured older sister, and Queen Street is where it happens. Galleries, antiques, a bookshop or two, homewares that make you want to move house. It is a street to walk slowly with something in your hand.

What we love about Queen Street is that it does not perform. There is no queue, no line out the door, no sense of anyone trying to be discovered. It is a street for people who already know what they like.

If you are the kind of shopper who buys one thing a season and wears it for five years, this is your street. It is also, not coincidentally, the philosophy we buy on. Our knitwear and blazers exist for exactly this customer: quiet pieces, good fabric, no expiry date.

Finish in Centennial Park, or keep going to Double Bay

You have two endings and they are both good.

Turn south and you are at Centennial Park, which is the closest thing Sydney has to a great civic lung. Ponds, enormous fig trees, horses, and a light in the late afternoon that makes everyone look like they are in a film. Walk it off. It is the perfect antidote to a long lunch and it is free.

Or keep going east and drop down into Double Bay, which is a different proposition entirely: sharper, glossier, more European in the way it wants to be seen. Coffee here is an event. If you still have energy, this is where the day gets a second act.

Either way, if the light is still good, the drive back over to Bondi at golden hour is the correct end to it. The road opens up, the water appears, and the whole Eastern Suburbs makes sense in a single view.

What the day actually asks of your wardrobe

Three things, in our experience.

Shoes you can do six kilometres in without thinking about it, because between Five Ways, Oxford Street, Queen Street and the park, you will. A flat leather sandal or a good loafer, nothing that needs managing.

A layer that earns its place. The temperature swing between a sunny footpath and a shaded terrace courtyard is genuinely significant, and the women who look most comfortable at three in the afternoon are the ones who brought a blazer or a knit and have been putting it on and taking it off all day without a second thought.

And one considered thing. Paddington and Woollahra are not places where anybody is trying hard, but they are places where everybody is trying. The distinction matters. One good piece, worn easily, is the entire local language: a beautiful trouser, a proper sunglass, a gold cuff. The rest can be plain.

That, in the end, is the same thing we have been saying on Gould Street for thirty years. Buy less, buy considered, wear it constantly, and let the city do the rest.

If you want to see what that looks like on a rack rather than a screen, visit us in Bondi Beach, twenty minutes from Queen Street with the wind behind you. And if you are reading this from somewhere considerably further away, we ship worldwide, including to the United States.