What size water bottle will it hold?

My water bottle that fits is one you buy that would be a plastic throwaway- a 16.9 oz. (500 ml). There is still plenty of room inside the bag, and I like the mesh on the outside, so, if it is a hot day, your bottle sweats some, it doesn't matter.

do the straps adjust long enough to wear cross body style?

Yes, I bought this bag because you can wear it crossbody, as I am traveling to Rome, and want to make it very hard for those pickpockets to get my bag. I am 5"4" and have ample strap room with plenty to spare to wear cross-body.

Does the 14 in measurement include the external side pockets? What does the main compartment measure>

I would say yes. Main compartment measures approx 13 wide x 10 deep. The side pockets are very flat against the purse unless you unzip them, then they open wide enough for a full sized water bottle, held by a mesh pocket. I have this purse in black and brown and use them every day. Inside compartment will fit my large wallet, checkbook, two eyeglass cases, keys, Kindle and lots of etc. Hope this helps.

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🧳 Travel Smart, Travel Secure!

COMFORT MEETS STYLE - Adjustable strap length (15" - 28") for a perfect fit, no matter your style.
STAY SECURE ON THE GO - Experience peace of mind with a 5-point anti-theft security system.
ORGANIZED FOR ADVENTURE - Multiple compartments including RFID-blocking slots for cards and passports.
TRAVEL LIGHT TRAVEL SMART - Weighing only 1.10 lbs, this bag is designed for the savvy traveler.
VERSATILE STORAGE SOLUTIONS - 19 mesh expansion pockets for your essentials like water bottles and umbrellas.

The Travelon Anti-Theft Cross-Body Bucket Bag combines style and security with its innovative 5-point anti-theft system, multiple organizational pockets, and lightweight design, making it the perfect companion for any traveler.

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