Pump and Dex in my FlipBelt and meter case with 3 syringes a spare vial of insulin and my meter + lancets/strips in either a pocket or in the glove box.
Everything goes in this. Meter & spare meter, strips, snacks, water, spare infusion set/reservoir/insulin vial, insulin pen & needles, spare oral meds, pens/pencils, phone, glasses, batteries, backup knife, backup pistol, first aid kit, trauma kit, fire starter, GPS, flashlight, spare flashlight, wallet, multitool, toothbrush, etc.
Used to use a fanny pack, but had to upgrade to a small book bag. I swear when you have some thing to put stuff in, you keep putting stuff in until you need some thing bigger to put stuff in. I guess women are the same way with purses.
A brown leather Fossil "Murse"
BG meter (including finger-poker and strips) in my pants pocket. "Accu-Chek Compact".
I occasionally have to get out a can of compressed air and blow the pocket lint out of the bg meter to stop it from throwing errors.
Insulin bottles and syringes in my shirt pocket.
I have a pump now but, back in my MDI days, I had this cool thing I got from my wife:
She got it in Korea and it might be faux (no double stitching?) but it works and holds two bottles and two syringes so who cares? It's a great thing to pull out in a bar...
I use a fanny pack. I'm looking to upgrade to some thing that has more room since the amount of junk I have to carry has gone up so much. Always carrying three days worth of stuff doesn't help keep the size and weight down either. I'll probably end up using my LBE, web belt, and butt pack from the Army. It will be a real fashion statement.
Eric, who is not a man but who is male and particular about what kind of bag he carries — "oh, Mom. I can't carry that. That's a purse." — had a JDRF backpack for 5 years, and when that fell apart I gave him a rather unique bag I picked up in Mexico 25 years ago. It's leather, tube-shaped, and unlike any purse OR man-bag I've ever seen. I think it was originally made to be a camera bag of sorts, but... just like Eric himself, it's unique and a little oddball.
His pump, however, goes into a little belted pouch with a slot for the clip & tubing to pass through. I've made four of these, just for him. One is just plain striped cloth (he calls it "Stripey"), but the other three have animal-head flaps — a frog, a monkey, and a zebra ("Froggy", "Monkey", and "Zeebie" are their names). In the long run he'll probably have a sort of utility belt for the meter as well, but for now he only carries the pump itself everywhere.
Small fanny pack. I carry a large phone in one pocket, keys in the other and everything else in a small fanny pack including wallet. I find it very convenient. I am not, nor have I ever been, a slave to fashion, or trying to impress anyone. :)
Women do have a bit of an advantage here, as you point out. When I was on MDI I just managed with pockets--those "pens" mostly do just look like that in a shirt pocket. But there's so much more junk involved with the pump that I finally broke down and got something to haul it around in. Mine is a black leather shoulder bag from Overland Equipment that I got at REI. Looks reasonably outdoorsy and manly and is roomy enough for my tester, extra strips and glucose tabs, along with a few other sundries. Now that I'm using angled-canula infusers, which are a lot less bulky than the 90° ones, I have room for an extra one of those as well.
Since other guys (and some women) just are going to feel obligated to tweak you for carrying any kind of bag around it's good to have your response worked out ahead of time. When anyone asks what I have in my "purse," I tell 'em "My pancreas."