Here on EG, I’ve been helping guys with their style for almost 15 years now. And there’s one piece of advice I still give, even after all this time: Fit First.
What’s this mean, exactly? Nail the right fit for your body, and everything else will fall easily into place. You can have a bunch of cool clothes, but if they don’t fit you right, you’ve already lost.
Pants, especially, are worth paying extra attention to. Tops have a bit of leeway when it comes to good fit. But pants? Pick the wrong pair and they could be too tight, too loose, squeeze you in the wrong places, flatten out your backside… the list of fails goes on and on.
Cue Flint and Tinder’s 365 Pant
The 365 Pant from Flint and Tinder is a garment we often recommend on EG. Why? It’s the ideal casual pant: A classic 5-pocket style, tons of menswear neutral-friendly colors to pick from, and just the right amount of stretch.
And the 365s aren’t just any pants; they’re like a trusty style wingman, ready to back you up whatever your body type or particular vibe you’re going with that day.
There are thousands of fans and a boatload of 5-star reviews singing their praises (which are particularly useful to read through when dialing in on your exact fit and size).
It’s all about fit first with these pants! They’ll give you that peace of mind and confidence in your look every time you wear them.
My pal Megan from Style Girlfriend and I partnered up with our friends at Huckberry to feature the
Check them out below, plus our thought process behind what we chose and why!
Outfit #1 With The 365 Athletic Tapered
If you spend your spare time squatting under a barbell, or you just happen to be a bit stockier on your bottom half, 365’s Athletic Tapered fit is made for you.
Effortless Gent’s Look
"Suited for both work and play, the 365 Tapered Pants are primarily made with cotton, which is then reinforced with stretch for extra mobility."
"Inspired by vintage blankets, the tartan pattern keeps things looking cool and classic, while the 100% cotton workshirt body and signature top-tier Relwen construction make this a great choice for outdoor treks."
"Quilted, flannel-lined, and stuffed with insulation, this heavyweight work jacket delivers truckloads of warmth in a roomy cut."
"Soft, stretchy, and comfortable when you’re on your feet all day long, they’re destined to be your first pick when you're staring bleary-eyed into your sock drawer in the mornings."
"Luca's Terra Low merges the style of an elevated Oxford with the comfort of a cushioned sneaker."
"Named after the hat worn by WWII Navy sailors during nightwatch, the “watch cap” was designed to keep heads warm and dry."
Style Girlfriend’s Look
"Suited for both work and play, the 365 Tapered Pants are primarily made with cotton, which is then reinforced with stretch for extra mobility."
"Their Pensacola Long Sleeve Polo elevates a classic silhouette with signature details like a woven undercollar, ribbon stitch detailing, and subtle branding touches inside the vents."
"It’s designed after vintage ranch jackets and cut with a modern fit that looks sharp but won’t get in the way when you’re traversing through the snow or bottling up your latest homebrew."
"The distinctive shape still maximizes the field of vision while minimizing glare, and the bayonet temples ensure easy wear for the modern cyclist and motorcyclist."
"Automatic diver watch suitable for scuba diving up to 200m depth. Rugged stainless steel case with uni-directional rotating bezel and screw-down crown. Black dial with luminous hands/markers for legibility in low light."
"Fully leather-lined for superior comfort and featuring a light-yet-sturdy rubber sole that delivers reliable traction without weighing you down, the Huckberry x Diemme Roccia Vet sets a new standard for heritage hikers."
Outfit #2 With The 365 Slim
If you’re a slimmer guy who has a hard time finding pants that don’t swallow you up, and you’re looking for casual pants that give off a more streamlined aesthetic, the Slim Fit 365 are right up your alley.
Effortless Gent’s Look
"Suited for both work and play, the 365 Slim Pants are primarily made with cotton, which is then reinforced with stretch for extra mobility."
"A truly foundational garment, this one is highly versatile and built to last forever."
"It’s the best quarter zip sweatshirt we’ve ever worn, and it’ll just keep getting better—softer with wear and guaranteed for a decade."
"They offer thermoregulating properties—all while being comfortable as hell—and are designed with New Mexico and Navajo-inspired patterns for a style that extends beyond shoes."
"While the Rockflex Boot parades all the hallmarks of a traditional hiking boot—eyelets, rugged soles, a padded ankle collar, and handy heel pull tab—it’s anything but your run-of-the-mill hiker."
"A waxed canvas jacket that’s effortlessly tough and steeped in old-school hunting style."
Style Girlfriend’s Look
"Suited for both work and play, the 365 Slim Pants are primarily made with cotton, which is then reinforced with stretch for extra mobility."
"They offer thermoregulating properties—all while being comfortable as hell—and are designed with New Mexico and Navajo-inspired patterns for a style that extends beyond shoes."
"The 10-Year Pullover is a truly American product, passing through the hands of 20+ American workers on its journey to your doorstep."
"A truly foundational garment, this one is highly versatile and built to last forever."
"Flint and Tinder teamed up with the leather experts at Golden Bear—to build an heirloom nubuck leather jacket in a classic bomber silhouette."
"With an updated leather, insole, and outsole, these chukka boots are a fresh take on a classic design, constructed from top-shelf materials that will cushion each and every step you take."
Outfit #3 With The 365 Straight
The Straight Fit 365 are perfectly trim, not tight, with a wider opening at the ankle. They feel very classic. If you’re looking for something that’ll stand the test of time, both in durability and aesthetics, this is what you wanna go for.
Effortless Gent’s Look
"Cut like a jean, feels like a chino, stretches like a performance pant."
"The Sawtooth Western Shirt is cut from breathable cotton slub chambray, textured for extra style points and a unique hand feel."
"Made with chunky textured yarn in a neutral marled shade, this criminally soft jacket is an invitation to break from the hustle, dial back the rush, and take it easy."
"The Quilted Waxed Vest embodies gritty conditions and white-knuckled hard work."
"Fully leather-lined for superior comfort and featuring a light-yet-sturdy rubber sole that delivers reliable traction without weighing you down, the Huckberry x Diemme Roccia Vet sets a new standard for heritage hikers."
"Soft, stretchy, and comfortable when you’re on your feet all day long, they’re destined to be your first pick when you're staring bleary-eyed into your sock drawer in the mornings."
Style Girlfriend’s Look
"Cut like a jean, feels like a chino, stretches like a performance pant."
"Wills meticulously separates the superfine cashmere fibers from molted goats to knit sweaters that are softer than a whisper in a library."
"Flint and Tinder’s CPO Boiled Wool Shirt Jacket is a sartorial salute to military precision and cold-weather strategy."
"For this iteration of our fan-favorite Huckberry Beanie, we opted for a handsome Donegal wool packed with warmth and interesting visual texture, in a timeless cuffed silhouette that never goes out of style."
"Designed for those who like to add an extra dose of sophistication to their outfit, Miansai meticulously crafts handsome, everyday pieces that go with nearly everything in your wardrobe."
"Each pair is a remarkable convergence of sugar cane, organic cotton, Amazonian rubber, and countless other eco-forward elements—culminating in a shoe that’s just as kind to the planet as it is to your style sensibilities."
Those are the 6 Looks Paired Up With 365 Pants!
That’s it! Did you like the outfits? Hopefully we provided you some inspiration, or at the very least, a place to start from, when wearing the 365 pants.
Remember, focus on fit first! And keep in mind, you can use ALL of these outfits, no matter the fit of 365 pants you choose. Just gotta pick the cut that makes the most sense for your body, and you can easily find the colors you need.
Hit me up on Insta DMs if you have any Qs.
