The Fall Shirt Guide

We’ve officially turned over a new leaf—it’s fall. You might have your closet stocked with all of the essentials, but what about the biggest shirting trends for the new season?
Read on to see the best fall shirts to stock up on.

THE WORK SHIRT

Finally, a shirt that works harder than you. Now don’t confuse this with a shirt you wear to the office. This work shirt gives you all the perks of looking like you put in the work, without even breaking a sweat.

Wear Your Work Shirt With:

• Dark jeans and a puffer vest layered on top.
• A white tee. Cuff the sleeves for a casual weekend look.
• With khakis or chinos and leather brogues for a day at the office.

THE CHAMBRAY SHIRT

This year-round choice should already have a top spot in your closet (it’s an essential). You have the options of the classic blue chambray, or switch things up with a colored version (grey gets our vote).

Wear Your Chambray Shirt With:

• Colored chinos and underneath a classic navy blazer.
• Dark jeans and chukkas for a smart-casual option.
• The real question is, what can’t you wear it with?

THE EASY-CARE DRESS SHIRT

What’s more satisfying than hitting “snooze” when your alarm goes off? Knowing you won’t be late thanks to an easy-care dress shirt that you don’t have to iron. It’s ready for work and ready to go in your carry-on over the holidays.

Wear Your Easy-Care Dress Shirt With:

• Dress pants and a coordinating blazer.
• Dark jeans and chukka boots take the cake on date night.
• Khakis, brown brogues & a matching belt.

THE SHACKET

It’s the perfect middle ground between a shirt and a jacket (hence the name) with benefits from both—a slimmer fit and a heavier weight in a workwear-inspired style. Head into unexpected weather with this perfect transitional layer.

Wear Your Shacket With:

• A T-shirt, jeans and boots for an easy, everyday look.
• An unbuttoned long-sleeve henley over a T-shirt when it’s extra chilly.
• Your favorite pair of distressed denim and a lightweight sweater.

THE FLANNEL

It can’t really be fall if you don’t have a flannel shirt. We’ve got plenty of options to add to your closet, whether it’s a classic Christmas plaid or a solid-colored and super-soft flannel.

Wear Your Flannel With:

• Jeans and brown leather boots for the classic heritage look.
• Unbuttoned, layered over a tee and jeans.
• Add a leather jacket and dark jeans for a night out.

THE DENIM SHIRT

Not to be confused with your chambray shirt—the denim shirt adds the man to manly. With a thicker fabric, it’s great for cooler weather and ideal for a work-to-weekend ensemble.

Wear Your Denim Shirt With:

• Khakis and chukka boots.
• Layer a crew-neck sweater on top if you’re wearing it to the office.
• If you’re going denim-on-denim, choose a different jean wash to mix things up.

THE STRETCH OXFORD

Oxfords have a special place in every man’s heart. Add stretch to them and you’ve got your new favorite button-down.

Wear Your Stretch Oxford Shirt With:

• Distressed jeans and a pair of Chelsea boots.
• Layered underneath a cardigan with dark jeans.
• Dress pants and dress shoes for the office holiday party.

THE TWILL SHIRT

This sturdy option is a great way to add a different texture to your wardrobe. Not to mention it’s a fan favorite in colder climates.

Wear Your Heavy Twill Shirt With:

• Jeans and sneakers.
• A brushed twill version is dapper enough for the office with a pair of khakis.
• Dark brown chinos and work boots.

Natalie Huey CEO & Founder