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Before I moved to New York City at 23 and started working full-time, I didn't understand the "weekend getaway." Obviously I'd had weekends before, but weekend trips with my parents in suburban Ohio were a rarity — to be fair there weren't that many places we could get to in two days — and once I was in college, the concept of a weekend became much more ephemeral (man, do I miss the days when I was able to meticulously manipulate my schedule to avoid classes on Wednesdays and Fridays).
Therefore, it was only when I started my first real "big city job" that I began to grasp the concept of a "weekend getaway." Leaving work early (i.e. 4:30 p.m.) on a summer Friday, rushing to Penn Station, hopping on the LIRR, and spending approximately 32 hours in the sun before straggling onto a Sunday evening train back to the city — the entire process made me feel like a sophisticated jet-setter. (Even though most of the locations I frequented were still only a stone's throw away from the tri-state area). But it was during these early exciting years of weekend travel — and stuffing my weekend clothing and shoes into my well-worn Longchamp tote — that I determined I really wanted to find the perfect weekend bag.
At first, I almost thought that I had invented the notion of a classy and beautiful weekend bag that wasn't the traditional backpack, roller suitcase, or gym bag. However, after a few Google searches, I determined that many others had felt the necessity for an aptly named "weekender" bag.
I first fell completely in love with the Marc by Marc Jacobs classic: the Delancey Weekender Bag, but I was paralyzed by the myriad weekender options I found online, and I noted the relatively steep price of the bag for my income bracket, so I didn't buy it. In fact, as the summer was ending, I didn't end up buying any weekender bag. I soon came to regret that choice.
When the next summer rolled around, I was truly upset to find that they had stopped making the Marc by Marc Jacobs weekender that I had coveted. I reached out to my friend who worked at Marc Jacobs, but she told me that my best bet was trolling eBay (which I am notoriously very very bad at). I wasn't able to buy it anywhere. Just like the Cole Haan Maria Sharapova flats that I had to continue buying in ugly colors on Amazon after they were retired, I had discovered another mythical unicorn product: the ideal weekender.
Over the last two years, I have become obsessed with finding the perfect weekender bag. I think it's partially because of the regret I feel at missing out on The Delancey, but I have read pretty much every single weekender shoppable article on the internet, and I still have not decided on which one is perfect for me. It's become basically the online shopping I do without thinking, which I am aware is pretty weird.
That said, you all get to benefit from my weird obsession. Using my extensive research, I have catalogued all of the best weekenders (IMHO) for all occasions and price points below.
These are the classic, clean, weekender bags of your dreams. Some are definitely more affordable (and more animal friendly) than the others, but if you want to carry a classic weekender and feel like a pilot in the '50s or a rugged day-tripper that smells of rich mahogany, these are the bags for you.
If your definition of a weekend away includes hiking, golfing, or a lot of squash, then these might be your faves. I'm also really into these bags because they can double as your gym bag.
If you're heading to Montauk or Napa for the weekend and you want to tote around your sundresses and Tory Burch flats in style, these are the perfect weekenders. My personal style is nowhere near preppy, but I still really covet this J.Crew tote with all of my heart.
Vera Bradley was my life in high school, and though I haven't busted my old tote out of storage in years, these floral and colorful bags are beautiful and classy in the best way.
If you want a weekender bag, but you don't want to spend too much on something you won't use from Monday to Friday, you can find great options below.
Disclaimer: I cannot afford any of these, but boy do they look cute. If anyone feels like buying me a Rag and Bone weekender any time soon, I will gladly accept the gift.