Effortless Gent

Five Ways to Wear One: Mid-Grey Flannel Trousers

by Beau Hayhoe  |  in Smart Casual

Grey flannel trousers – a boring pair of pants that should have no part in your wardrobe? Think again.

Today on EG, we’re talking five ways to wear mid-grey flannel trousers through late fall and well into winter.

The flannel trouser – particularly with a matching flannel jacket – is wrongly pegged as a boring, safe style choice.

It might look conservative, but that’s not to say it can’t be worn in ways that are style-forward and versatile.

Who’s with me?

Thanks to modern brands like J.Crew, the flannel trouser is now seen much the same as dark blue denim or khaki chinos. You can mix and match them with nearly any other seasonal style staple.

The pair of trousers we’re talking about today acts much the same way. It’s a mighty fine menswear purchase, if you ask me.

What exactly comprises that list?

We’re looking for a well-made, wool flannel trouser with premium fabric. So cheaper options are out of the running.

You can go high on the price spectrum. But more affordable will work just fine if you’re still in the experimentation stage with pants that aren’t your usual denim or chino.

The Tyler trouser checks both boxes.

But what about fit and care? That’s another matter entirely, and it’s an easy challenge to meet if you know what to look for.

Fit and Care

First things first: yes, pleats are back en vogue in some echelons of high fashion. But regular guys like you and me look better without that extra fabric along the waist line.

Editor’s note: Pleats aren’t always a bad thing, especially the modern interpretations you find nowadays in places like J.Crew, Banana Republic, even Gap.

I’ve long been an advocate for slim, no-pleat pants, but over the last year or two, have started to get back into pleats because they’re more comfortable for me and give me added ease of movement, while still looking slim and tapered.

It’s all about finding the silhouette that works for your body, with a taper to the leg opening and overall flattering shape (not too slim, not too loose).

In general, if you’re of average build, you don’t need pleated pants, though you could pull them off if you wanted to. If you have bigger or more muscular legs, pleats can be your friend.

This lends itself to a slimmer look, too – and that’s how your pants should fit.

Look for pants that are tailored but not overly tight. And you need room to move in the seat and thigh.

Reach for a slim, tapered, or modern slim-straight cut. Think the difference between J. Crew’s 484 denim and the 770 jean.

This brings us to another important point. Knowing your measurements is essential. That goes for which waist size and inseam size fit you best.

If you’d prefer to dial things in completely, get measured by your local tailor. This is a guy you ought to have in your corner to begin with. That will make it easier to take the plunge and order these trousers online.

So, the pants are ordered and shipped.

They’re at your door, in your hands.

How do you keep them lasting through all the style scenarios you have in mind? Here we go.

The consensus – and the instructions – dictate that 100% wool pants should be dry-cleaned. And also treated with care before that.

What does that mean exactly?

Coming from a guy who’s run through too many plastic hangers, investing in some closet storage upgrades – like option #4 on that list – increases the longevity of your trousers.

What if you spill something on them?

Spot-cleaning it or blotting the trousers with a small amount of soap and water might stave off the inevitable in a pinch. But dry cleaning is certainly the way to go.

Now that we’ve put the abject horror of spilling on your new flannel trousers out of mind – onto the outfits! You’ll love them – promise!

#1. The Tailored Classic

Five Ways to Wear One: Mid-Grey Trousers

The natural way to wear tailored flannel trousers is alongside tailored style staples. That’s the way we’re going in outfit #1.

For the perfect top layer, we’ve got a quilted jacket in a handsome shade of navy.

For extra comfort and warmth in the chill of fall, a premium cashmere zip sweater is a solid choice. Go with a shade of tan/camel that contrasts with the navy jacket.

That rock-solid combination is grounded nicely with a seasonally appropriate burgundy tweed tie.

Worried you may need to chase villains through the street? Rugged-refined leather hikers give this outfit a bit of an English countryside air.

And if you haven’t caught on yet, a classic white Oxford is a four-season essential that grounds the whole look in classic style.

Lest we forget, a slim, refined timepiece is a low-key, stylish finishing touch.

Pop the collar on the jacket and enjoy that stroll to Sunday brunch even more. That’s where we’re going, right?

#2. The Rugged Throwback

Five Ways to Wear One: Mid-Grey Trousers

Thought flannel trousers could only be worn with more tailored looks? Think again.

An essential chambray shirt is the perfect contrast to mid-grey flannel trousers in terms of texture and style. It’s polished-meets-casual, especially in a cold-weather fabric like chambray.

If you’re wary of trying a vest, reach for one that eschews the typical all-black construction. Go with a heavyweight wool vest in a striking plaid pattern.

Layer up with the above quilted navy jacket, while you’ve got it handy (you bought it, right??). Yes, the look conjures up throwback, vintage-inspired style – but the flannel trousers give this ensemble a bit more polish than dark denim would.

Ditch the pocket watch in favor of a rugged wristwatch. Add in textured charcoal socks that are made in America.

And strongly – I mean strongly, – consider reaching for a pair of deep brown suede longwing boots. Their texture and color are perfect for fall. They’re wearable with mid-grey flannel trousers as well as slim chinos. And they ground the outfit quite handsomely.

#3. Casual and Cool

Five Ways to Wear It: Mid-Grey Trousers

Don’t reserve you flannel trousers for dressy, tailored wear only. You can take that same staple and pair down your look – within reason, of course.

So while you won’t see a graphic T-shirt alongside your mid-grey flannel trousers, you will see other essentials that straddle the line between laid-back and formal.

Take the classic white Oxford. It’s crisp and sharp, yet it pairs nicely with a deep indigo crewneck. Feel free to untuck the shirt a bit and roll up the sleeves.

The focus of this piece is the flannel trousers. But you’d do well – extremely well – to pick up those beautiful tan leather sneakers.

Did you write that down? You certainly should.

Striped red socks add comfort and a dash of color. And what’s better than a brown leather watch made from Red Wing shoe leather?

#4. Classic and Tailored

Five Ways to Wear It: Mid-Grey Trousers

Just as easily as you can go casual with your flannel trousers, you can dress them right back up in the blink of an eye.

Take a classic navy jacket and team it with other straightforward, reliable staples.

A white twill shirt from Twillory is a nice place to start. And an essential Ties.com pocket square is another small touch that offsets the navy sport coat nicely.

Where’s the real star of this outfit? That vintage-inspired, visually appealing windowpane vest. It adds just the right amount of pop without taking too much away from the outfit.

Beautiful wingtip boots from the heritage footwear makers at Johnston & Murphy seal the deal. They bring both seasonally appropriate texture and a bit of durability to the look.

And a slim, refined dress watch falls right in line with the fine tailoring of this ensemble. Again, don’t forget made-in-America socks. Your feet will thank you.

#5. Fashionable and Functional

Five Ways to Wear One: Mid-Grey Trousers

You didn’t think we’d get through this entry without bringing a chambray shirt into the fold, did you?

A classic chambray shirt is the perfect match for flannel trousers – especially in terms of texture and color.

The shirt will pop nicely against that beautiful suede jacket. It’s rich in color, well-made, and affordably priced from the folks at Beckett Simonon.

The deep brown suede jacket and blue chambray shirt are offset nicely by super-sleek black Chelsea boots.

Keep the contrast going with other like-minded accessories. Like a slim black leather dress watch. And sharp-as-heck Aviator sunglasses (from a place you might not expect – MVMT Watches).

Finally, striped red socks complement the blue chambray shirt and grey flannel trousers quite nicely.

Versatile and Stylish Trousers

It’s not essential to own every single one of the pieces mentioned above. But there’s a lot that can be done with a pair of well-made, slim-cut, versatile flannel trousers.

From the casual to the formal, there’s little that can’t be done when it comes to seasonal style.

If you snag the right pair (like the one featured in this article), it will add a dose of unexpected variety to your wardrobe.

After all, we all need to shelve our dark blue denim and chinos every once in a while, yeah?

Take good care of your flannel trousers. You’ll be able to test out these five outfit combinations again and again next fall and winter. Plus a few more after that.

How do you style your flannel trousers?

Would you add or subtract any pieces from the ensembles above?

Published on November 10, 2016, Updated on September 5, 2023

Category: Smart Casual

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