A Guy’s Guide: How To Style a Flannel Shirt for Fall

As fall approaches, it’s time for men to take the flannel shirts out of storage, stock up on fresh, new options and prepare for the chilly season. Thinking about different styling options can allow you to change up your look depending on where you’re going and the occasion. You’ll look stylish in a flattering flannel shirt and stay warm in the process.

Casual: Running Errands/Post Workout

You have so many options when you want to take a casual approach to wearing a flannel.

One option is to wear it open with a long-sleeved henley underneath, paired with jeans. Another option is to button up the flannel, throw a vest over it and complete the look with dark jeans. If you prefer a different style, skip the vest and wear the buttoned-up flannel with jeans.

Smart Casual: Dressing up a Flannel

Many think of a flannel shirt as strictly casual, but it’s also about what you pair with it. For example, if you want a smart casual look and want to dress up the flannel a bit, opt for pairing the flannel with pants like chinos or khakis. However, make sure the pants are ironed. Leave the sneakers at home and put on Oxfords or loafers instead. Slip on an attractive watch as a finishing touch.

Fall Date Look

How you wear your flannel on a fall date depends on where you’re going. If it’s an outdoor outing like picking apples or pumpkins, leave khakis and nice shoes at home and wear jeans and boots that can hold up through uneven and potentially muddy ground.

For an indoor date, you’ll want to look into if there’s a dress code where you’re going before even deciding what you’ll wear. If you’re going to a low-key spot, like a cafe, there’s no problem wearing a long-sleeved crew neck with a flannel open over it. Going to slightly more elevated places may call for nicer pants like corduroys or chinos. If the venue has a formal environment, leaving the flannel at home may be best.

Grabbing Drinks With the Guys


The same rules would apply to grabbing drinks with the guys as they would for going out on a date. If you’re going to a casual bar, feel free to wear an outfit like a hoodie with an open flannel over it and a nice pair of dark jeans. For places that are a little more upscale, skip the flannel or wear it buttoned up. You’ll want to pair it with pants like khakis or chinos and wear loafers or Oxfords.

Keep Colors and Patterns in Mind

While a flannel can easily complement a pair of jeans or chinos, you also want to ensure the colors and patterns work together. There are so many different shades of jeans and chinos and a range of plaid colors and patterns that it can seem overwhelming to pair them.

The most useful way to decide which flannel goes best with which pair of pants is to spread them out on the bed. Don’t overthink it too much. Lay the pants out that you want to wear and place the flannel over them. If your immediate impression is that it’s not the best pairing, move on to a different flannel or pants.

Deciding what to wear underneath is the easy part. Usually, a white short-sleeved or long-sleeved henley or t-shirt, or even one in gray or black, can offer a great base to the look.


Buttoned vs. Unbuttoned

There are a few factors to consider when deciding whether or not you want to wear your flannel buttoned or unbuttoned. Where you’re going is the first thing to think about. When you’re headed to a venue like a dive bar, you can wear pretty much anything and look great.

However, if you’re thinking of going to places with less beer on the floor, you may want to lean toward wearing the flannel buttoned. If the place falls somewhere in between, like a cafe, it’s fine to wear it buttoned or unbuttoned.

The Condition of Your Clothes

Whether you’re going on a date, running errands or heading out with friends, avoid pairing your flannel shirt with distressed clothing. You should also skip wearing dirty clothes or accessories, such as grungy sneakers you haven’t cleaned in a while or jeans with stains or rips.

Tucked in vs. Untucked

One time you never want to tuck your flannel in is when you’re wearing it open over another top, like t-shirts or mens hoodies. You may also want to skip it if you’re wearing jeans. Typically, tucking it in looks best with pants like chinos or khakis.

When you want to wear it untucked, be mindful of the flannel you choose. Some flannels that aren’t well made can look sloppy rather than stylish. Pick the right flannel, and it can look fantastic untucked with jeans or pants that are more formal.

Plan Your Fall Flannel Looks Ahead of Time

So many men are all about fall flannel looks for autumn. Buy your favorite flannels now to ensure you get the ones you want and be ready to wear them as soon as the chilly weather approaches. Don’t forget to stock up on pants and footwear that complement your new purchases. Choose the right options, and they can easily help you construct many outfits through each season.

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