The Shoes That Earn Another Fall

Every fall, I notice the same thing.

I don't suddenly need new shoes.

I simply start reaching for different ones.

Without thinking about it, a handful of pairs move to the front of my closet while others stay exactly where they are. It isn't because they're trendy or new. It's because they've already proven themselves through airports, work trips, weekends, rainy mornings, and everyday life.

These are the five pairs that quietly earned another season.

The Boots That Do Double Duty

These Sorel Evie II boots aren't just my rainy-day boots.

They're the pair I automatically reach for when the forecast looks questionable or I know I'll be walking more than usual.

They're waterproof leather with full-grain suede, which means I never have to think twice about puddles, changing weather, or chilly mornings. They work just as well running errands around town as they do exploring somewhere new.

I wore these all over Iceland.

Waterfalls. Airports. Long days on my feet. Every kind of weather imaginable.

Somewhere during that trip, they stopped being "boots I liked" and became boots I simply pack without thinking.

The Loafers That Dress Up Everything

Every fall, my Rothy's Driver loafers quietly take over.

They're just a little more substantial than my summer shoes, which makes them feel right as the weather starts to change. They instantly make jeans and trousers feel more polished without sacrificing comfort.

And then there's my favorite feature.

They're washable.

After conferences, airports, and miles of walking through unfamiliar cities, I throw them in the wash and they're ready to do it all again.

That's the kind of maintenance I can get behind.

The Sneakers I Never Put Away

Every year there's a moment when I stop reaching for my Clarks sandals.

Not because I want to.

The weather simply changes.

That's when my Onitsuka Tigers quietly take over.

They're my favorite sneakers for walking around town, grabbing coffee, running errands, and travel days that don't call for boots yet. They're comfortable enough to wear for hours, but still feel intentional enough that I don't feel underdressed.

They've never really had an "off season."

They just get more mileage in the fall.

The Heel That Always Earns Another Trip

If you've followed Looks More Expensive for a while, this one probably won't surprise you.

I own...a lot...of Sam Edelman Hazel pumps.

Enough that I've stopped pretending I need a different heel.

Every conference.

Every client dinner.

Every presentation.

They're the first heels I pack because I already know exactly how they're going to perform. Comfortable enough for long days. Classic enough to work with almost everything in my suitcase.

When something works this well, I stop looking for something better.

The Coastal Boot That Earns Its Place

Most fall shoe lists probably don't include waterproof deck boots.

Mine does.

Because my real life includes chilly mornings at the marina, afternoons on the boat, and evenings when the wind off the water reminds you summer is officially ending.

My Huk Rogue Wave boots were made for exactly those days.

They're practical without feeling bulky, comfortable enough to wear for hours, and they're the pair I'm always grateful I brought.

For where I live, they belong in every fall rotation.

Why These Five Stay

I don't build a completely new wardrobe every season.

I let the best pieces earn another one.

These shoes aren't here because they're the newest purchase or the biggest trend. They're here because I keep choosing them.

Again.

And again.

And after hundreds of wears, I think that's the best compliment a pair of shoes can receive.

Because when a shoe quietly earns another fall, it usually earns the one after that, too. -LME

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