The Secret to Great Style? Great-Fitting Pants

The Secret to Great Style? Great-Fitting Pants

Spilling style secrets...
mens casual pants outfits for 2024

By Team SG | Last Updated: Mar 1 2024 | 7 min read

This is one of those sneaky, hiding in plain sight-style tips that we want every guy to know.

It may seem obvious, but pants that fit you—really, really fit you—make the difference between an outfit that women love to see men wearing, and an outfit that’s just…meh

Because pants that are too tight or too loose, pants that droop, or that just aren’t the right cut for your body? Ugh, such a bummer. Like seeing a beautiful man rocking a rattail. 

Truly, nothing wrecks an outfit faster than a bad fitting pair of pants. 

That’s where the 365 Pant from Huckberry comes in.

Huckberry Flint and Tinder 365 Pant fits

It’s a classic 5 pocket pant with a variety of colors to choose from, and the perfect amount of stretch. Even better? They come in fits for every body: straight, slim, and an athletic tapered fit for all the soccer players out there. Get ready because when you put them on, you’ll FEEL how good they fit. And if you’ve got some “words of affirmation” people in your life, they’ll tell you how good they fit, too. 

Athletic Tapered Fit

The athletic tapered fit offers extra room in the seat and thighs for all those with a little more leg (and butt) to love. 

huckberry flint and tinder 365 slim fit pants

Slim Fit

The slim fit stays narrow all the way down the leg. Cuff it in the summer to show off a little ankle, or sport your favorite “see and be seen” socks when the temperature dips. 

huckberry flint and tinder 365 straight fit pants in dark navy

Straight Fit

The straight fit pant’s slightly wider leg opening not only feels comfortable, it’s on trend, too. Skinny pants are out, while a silhouette that suggests you could be putting in extra reps on the calf machine at the gym is in.

As for the rest of your look, now that you’ve tackled fit first? We can help with that!

Huckberry enlisted Style Girlfriend and our pal Barron at Effortless Gent to share outfit ideas featuring this particularly fantastic pair of pants.

Get inspired with six men’s casual pants outfits featuring the 365 Pant, below.

Outfits #1 and 2: The Athletic Tapered Fit 365 Pant in Charcoal

365 pants athletic tapered fit outfit, mens casual pants outfits

SG SAYS: Here at SG HQ, we’re suckers for a neutral color combo. So this navy and olive green outfit is right up our alley. Swap the boots for something more casual if there’s not inches of snow on the ground where you live right now.

RELATED: 5 Days, 5 Ways to Wear the Huckberry 365 Pant


EG SAYS: The charcoal colorway of these Athletic Tapered pants inspired me to go a bit more rugged with the look, but still keep it polished enough for city boys like myself. The brushed flannel shirt is the perfect soft and cozy layer for your cold weather outfit, and the quilted waxed rancher jacket will keep that warmth in.

I finished it off with a two-tone suede sneaker, equally cozy camp socks, and an easy-to-wear army green beanie.


Outfits #3 and 4: The Slim Fit 365 Pant in Earth

slim 365 pants outfit, mens casual pants outfits

SG SAYS: Is there anything as instantly cool-boosting as a leather bomber jacket? Throw it on over a hoodie and 5-pocket pants and suddenly you’re giving Miles Teller a run for his money as the young upstart looking to dethrone Tom Cruise as the best pilot at Top Gun school.


EG SAYS: I Iove the richness of forest green, and it goes so well with the darker khaki pant color. Contrast it with an off-white T-shirt, which frames your face nicely under the quarter zip’s stand-up collar. Interesting (but still subdued) outerwear pieces are always the way to go—in this case, a black watch waxed canvas jacket.

And to finish it all off, a pair of patterned wool socks inside handsome brown leather hiking boots.


Outfits #5 and 6: The Straight Fit 365 Pant in Dark Navy

Flint and Tinder 365 pant straight fit outfit, mens casual pants outfits

SG SAYS: Say it with us…cozy layers are welcome here. Don’t stop at the cashmere sweater; go ahead and add an overshirt that looks like you could take a nap under it if the sleepies hit.

Then, top it all off with a beanie that you won’t want to take off til spring.


EG SAYS: I wanted to put together something a bit more outdoorsy (in an “I’m on a ranch” type of way) with the last of these men’s casual pants outfits.

RELATED: Style Girlfriend and Effortless Gent Style Everyday Sneakers

I love the shell snap buttons and unique pocket flap / yoke detailing on this denim shirt. If it’s cold, the chunky marled sweater will keep you toasty, and for a bit more warmth (but not too much), the quilted waxed vest does the trick. I contrasted this look with heritage-inspired, Italian-designed hiking boots, because I mean, why not?


As always, thanks for supporting the brands like Huckberry that make Style Girlfriend (and Effortless Gent for that matter) possible!

From the collective hive mind of the team at Style Girlfriend.