A Weekender for Every Summer Getaway

Prepare for your summer trips with one of these simple but classic bags.

I can’t be the only one hoping and praying that we’ll have a shot at summer, can I? Weekends at the lake with friends, bachelorette parties and trips home to visit the fam are all on my current agenda. For quick trips like those, you do not need a rolling suitcase. Instead, opt for one of these perfectly sized weekender bags. They will fit all your essentials for a weekend away and you’ll look tres chic while carrying them to boot. In the market for a more classic look? We have something for you. Looking for a bag to just toss things in and go? Ditto. So check out our picks below and dream of where you will be heading for the weekend the second the work day ends on the perfect summer Friday.

Leatherology “Kessler Duffle” ($590) - Leatherology has the softest leather you will ever get your hands on. Their travel products are some of my favorites and you can have everything monogrammed or hand-painted with your initials. This weekender is perfect for a weekend in the Hamptons or a trip to upstate New York. It is timeless and well worth the price tag.

Photo courtesy of Leatherology

Madewell “The Essential Overnight Bag in Canvas” ($158) - Madewell’s totes are my favorite; I throw my laptop, lunches, etc. in them for work and they last a lifetime. Needless to say I feel the same way about their weekender. It has separate compartments for your shoes, laptop, keys, cell phone, etc. And just like all their other leather/canvas goods, you can have your weekender monogrammed for a cute personal touch.

Photo courtesy of Madewell

Cuyana “Triple Zipper Weekender” ($285) - My friend introduced me to Cuyana about a year ago when she was looking for a new purse. It is designed with three compartments to make packing and organizing a breeze. Cuyana is also an environmentally friendly brand and have has pledged to use ONLY sustainable materials by 2022. So you can look good and help the environment at the same time. I’d say that's a win-win.

Photo courtesy of Cuyana

Lo & Sons “The Catalina Deluxe” (on sale for $89) - Another eco-friendly brand on the list, Lo & Sons creates its bags, backpacks and accessories out of recycled water bottles and sustainable organic cotton. This model has a separate bottom compartment to store your shoes because who wants their dirty soles touching nice clean clothes (not me). It also has a strap on the side just in case you need to bring a carry-on -- you can slide it right on and not have to worry about your weekender falling off while running through the airport.

Photo courtesy of Lo & Sons

Sole Society “Lacie Weekender” ($89) - Looking for a vegan friendly bag? Try this classic style from Sole Society. It is no frills, simple and is what I always picture when I think of a weekender bag.

Photo courtesy of Sole Society

L.L. Bean “Hunter’s Tote Bag” ($40) - Want to just throw your clothes in a bag and rush out the door? Stock up on these L.L. Bean totes. While not a classic weekender they are the best carry-all bags. The SI Swim team just switched over to these totes from our old Lands’ End versions on shoots. Everyone fights for the army-green bag because it is so durable, water-resistant and fits everything you could possibly need for a weekend away or a photo shoot on the beach. SI producer extraordinaire Cindi Blair has the camo version with a monogram and I may need to follow suit and order that exact design for my weekend trips to the beach. 

Photo courtesy of LL Bean