The #1 Style Hack I’ve Been Preaching For Years Is Still True Today

by Barron Cuadro  |  in Style Tips

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 Flint and Tinder 365 in a few outfits. We both took 3 pairs, one in each fit, and put together looks with our own signature spins.

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

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.

Style Girlfriend’s Look

Here at SG HQ, we’re suckers for a neutral color combo that’s not black and white. Or navy and black. Or black and more black. 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.

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

I love 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.

Style Girlfriend’s Look

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.

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

I wanted to put together something a bit more outdoorsy (in an “I’m on a ranch” type of way) with these navy pants. 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?

Style Girlfriend’s Look

Say it with us…cozy layers are welcome here. Don’t stop at the cashmere sweater; 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.

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.

This article is sponsored by Huckberry but all opinions and recommendations within are those of Barron and the team at Effortless Gent. You can read more about this here.