I packed for a 5-day trip using the $395 Cuyana leather weekender - it fit enough gear to run a half-marathon, attend a nice dinner, and explore the city

• On principle, I never check a bag when I travel. For years, I've relied upon the Cotopaxi Allpa 35L for packing as much as two weeks worth of clothing.
• Recently, I started using Cuyana's leather Triple Zipper Weekender ($395) as an investment into more stylish - but still functional - luggage.
• The Triple Zipper Weekender is split into three compartments. It has two open pockets on the side, and one in the center with three side pockets for loose knick-knacks and essentials.
• I packed for a five-day trip that varied from running a half-marathon to attending a fancy dinner using the Weekender as my carry-on. It's well designed, roomy, and beautifully made.

The last time I checked a bag, it was six years ago and I was moving to New York from the Midwest. In the years since, physics-defying bags like Cotopaxi's Allpa 35 ($200) have made an otherwise masochistic carry-on-only rule effortless to live by, even on two-week international vacations.

Recently, though, I upgraded to Cuyana's Triple Zipper Weekender for the trips on which I want a more stylish companion than the burly blue polyester and ballistic nylon bag. At $395, it's not by any means a cheap investment, but a few things make it easier to justify: a great design, quality leather that should grow even more supple over time, a timeless aesthetic that will age gracefully, and the comparative prices of similar leather weekenders with designs I didn't find nearly as useful.

Cuyana's Triple Zipper is made in Turkey from premium pebbled leather, has three compartments for organized packing, and three large interior pockets in the main compartment for items like shoes and loose essentials. The crossbody strap is removable, it has small metal feet for bottom protection, and there are two slim side pockets for things like snacks and a travel wallet. You can also have it monogrammed for $15 if you want. It's a great example of function and form intersecting.

This is the bag I packed when I went home to meet my boyfriend's family for the first time. And it's the one I plan to pack for an upcoming five-day trip that ranges from running a half-marathon to dressing up for a five-star dinner to exploring the city.

I fit everything you see below into the Triple Zipper: seven shirts, four pairs of socks, three pairs of shoes (heels, sneakers, sandals), two exercise tanks, two pairs of pants, one pajama set, one pair of leggings, one sweater, one dress, undergarments, one baseball cap, one book, one laptop, the T3 curling iron I use to cheat my way to a loose blowout look, and other travel essentials (my favorite Passport Holder, the the Mejuri Travel Case for jewelry, the removable pouch included in the Vanity Case Set for makeup, and my tiny but powerful Jaybird Vista earbuds).

After packing everything you see above into the weekender, my bag looked like this: stuffed, but zipped and organized. I put my chargers, inflatable water bottle, everyday wallet, toothbrush, and some snacks in another small purse.

With fewer things inside, you can clip the thin leather strap on top to the opposite compartment in order to keep the silhouette compact. You can use this for three-day trips just as well as trips double that duration.

In the outer side pocket, you can see the blue passport holder I keep there for easy access while traveling. The pockets are relatively deep, but the holder is designed for airplane tickets, so it's tall enough to peek out a few inches.

Typically, I like to keep one external compartment organized into labeled cloth bags for undergarments, electronics, and travel essentials like my wallet and toothbrush, but that's a) difficult to decipher in pictures and b) better for trips that require fewer pairs of shoes.

Internally, I used the three side pockets for my makeup bag, the jewelry organizer, sandals, and perfume. Unlike many weekenders, the Triple Zipper has nailed the just-enough organization factor; there aren't so many pockets I forget which holds what. Ultimately, I know exactly where each item is without dumping the contents out.

The Cuyana Weekender is leather and a true duffel weekender, so it can fit less than my Cotopaxi Allpa 35 and isn't as lightweight, but it is a beautifully made, well-organized, deceptively cavernous bag that I will use for years to come for both short and long domestic and international trips. If you're looking for a stylish weekender with plenty of space and elevated organizational design - and you can justify $395 on a purchase comfortably - I highly recommend checking this one out for yourself.

Cuyana Triple Zipper Weekender, $395

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