How to Transition Your Wardrobe for Fall (Without Buying a New One from Scratch)

We’re getting a hint of cooler weather in our corner of the world.

Cool enough to require pants and long sleeves for a Friday round of golf last week.

But the season changes slowly, and not all at once. Case in point: it was 87 degrees when Friday night football kicked off this week.

In other words, swapping out your wardrobe for fall can be tricky.

The Loafers & Legacy approach

If I were to sum up the Loafers & Legacy approach to this time of year, I’d say this: keep most of what you wore in summer, add a small number of layering pieces, and shift fabrics and colors over four to six weeks.

Why to change slowly

Early fall means cool mornings and warm afternoons.

Keeping the summer pieces that still work and adding layers you can take off covers both ends of the day.

It also shows you what you actually reach for before you buy anything new.

Layering pieces

These pieces let summer clothes keep working into October. Most men already own a few of them.

Overshirt or shirt jacket

I’ve come to love wearing an overshirt.

You can wear a lighter weight overshirt open over a T-shirt or polo when you need just a enough cover to take a little chill away.

*The Dutton Denim Work Shirt from Turtleson is a great lighter-weight overshirt*

When it’s colder or you’re spending more time outdoors, you can wear a heavier weight shirt jacket buttoned up over a sport shirt or crewneck.

*The Chamois Shirt in Traditional Fit from L.L. Bean is ideal for extra warmth*

Lightweight quarter-zip or sweater

Choose a merino or cotton blend that can go over a collared shirt and come off by lunch.

Merino crewnecks are easy to find in every price point, and if you want something with a little more sauce, you can always go for a quarter-zip or hoodie.

*This Italian Merino Crewneck from Nordstrom layers nicely and looks great on its own*

Unstructured jacket or chore coat

This covers the days that need more than a sweater but less than a coat.

*The Classic Chore Coat from Flint & Tinder at Huckberry is durable and dependable*

Fabric and color

The core of a fall outfit is often the same as a summer one. What changes is how heavy the cloth is and how dark the colors are.

Linen and seersucker are first to leave the rotation.

Lightweight chinos give way to heavier twill and then corduroy.

Colors move from white, light blue, and khaki toward olive, navy, brown, and gray.

A summer shirt in a darker color often works through October.

Footwear

Shoes are the easiest place to show the change in season without changing the rest of the outfit.

Canvas sneakers and boat shoes head to the sidelines first.

Suede loafers and leather sneakers cover early fall, and chukkas or boots come in once mornings are consistently cold or wet.

*The Paul seuede chukka from Frye delivers easy versatility*

What to put away

Put away only what you’re sure you won’t wear for the next six months. Keep a few short sleeve shirts and lightweight chinos in rotation for warm days.

Wash or dry clean everything before you store it, because stains and body oils set over months.

Store clothes in breathable cotton bins or garment bags rather than sealed plastic, and add cedar where you keep wool.