Outfits: how to look interesting in your comfiest clothes

What to wear on winter weekends if you want to avoid a sea of sameness.

One of our paid subscribers recently asked us how to bring more personality into her weekend outfits, when dressing for comfort is the primary objective. Her kids were constantly mistaking her for other mums on the Saturday morning sports field…all those black puffers, leggings, baseball caps and trench coats blurring into a sea of sameness.

It’s normal to reach for ultra comfortable, easy, ‘safe’ clothes on the weekend — especially when it’s 6 am, 6 degrees, and you have about 600 things on your mental to-do list. But in her desire for specificity amidst the sameness, our dear subscriber has touched on a truth about personal style: it acts as a kind of invisible string between us and the world, keeping us tethered to ourselves and making us more visible to others. Or, at least, the version we want to make visible.

Deciding on this version of ourselves is the hard/exciting part. It involves knowing what we like, what our taste is, and being confident in how we make choices. Committing to a unique personal style is, in this regard, a pretty powerful tool for realising what makes you unique as a person, too.

Amy Smilovic wrote about this recently, essentially explaining that the habit of fine-tuning your style can strengthen your capacity to fine-tune other aspects of your life. You become a better problem solver, more adept at adapting, more sure of your decisions. Sounds pretty good, no? Also sounds like effort, to be fair.

But it doesn’t need to involve starting a wardrobe from scratch. If we start with the basics, it just means asking ourselves how we want to feel in our clothes. And in 2025, despite the recent surge in searches for bandage dresses, we’d hazard a guess that most of us want to feel comfortable. Maybe it’s a uniquely Australian quality, but we crave that kind of effortless, easy, relaxed fit that still gives us room for playful self-expression and maybe a dash of glamour (?) thrown in, if we want it (we do).

In this week’s newsletter, we’ve compiled five outfit ideas that get you there. Ideal for weekend runarounds, cheering from the sidelines, schlepping your market haul to the boot, sipping hot coffee in the cold air, paying for a Bunnings sausage. Whatever it is.

We hope these will spark some ideas for how you can look at your own wardrobe in a new light — to find a truer version of your personal style without sacrificing any of the creature comforts we all love (elastic waistbands and all).

Next week, we’ll give you some ideas for when you have no choice but to reach for the puffer jacket with interesting padded jackets and luxe layering options. Until then, check out our Pinterest board for winter weekend inspiration when you really want to wear not much at all.

Thanks for being here with us.

Sophie + Annie xo

The Saturday morning gauntlet

Sweats are like the stock cube of weekend style: if we simmer down every other element, we’re left with just the essence of a truly heroic commitment to comfort. If you’re faced with a situation where sweats are just about the only thing that’ll do (but you also want to look like you care), reach for a long overcoat to balance out the casualness. Sharp sunglasses and diamonds (ahem, cubic zirconia) kick it into fourth. No more blending in during those Saturday morning soccer field sideline sessions.

Gilda Ambrosio

CAMILLA AND MARC / Delta Plaid Trench — $750

ASSEMBLY LABEL / Cashmere Polo — $220

BASSIKE / Front Seam Rib Long Sleeve T-Shirt — $170

PETE PAREO / Vintage Blue Track Pant — $220

CABLE / Cord Cap — $69

RELIQUIA / Fia Necklace in Silver — $229

RADICAL YES / Both Ways 2.0 Velcro Sneaker — $269

DEERING / Bibi — $350

POPPY LISSIMAN / Spice Sac Swiss — $220

ASSEMBLY LABEL / Cashmere Polo — $220

Pinterest

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The Sunday stroller

Swap out the floor-sweeping wool coat for a fuzzier version. Layer over your comfiest jeans and loafers for a Sunday coffee and DIY mission. Yes, we’d prescribe faux fur for a Bunnings run. Very Elizabeth Taylor coded. Yes, you can definitely pull it off. This is Sophie’s ultimate weekend uniform. Even leggings and sneakers would work here. Could even be better? Try it and let us know.

Kaia Gerber