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One thing I love about winter? Cozy sweaters and knee high boots. Better yet if the boots are waterproof! This sweater dress is an oldie but goodie that demands to be worn with tights or leggings. When I wasn’t on the insulin pump, that was not a problem. But how to wear it without making it obvious that I am a diabetty?

Well, given the title of this post, I’m sure you’ve figured it out. The cowl neck design is perfect for disguising my pump! I wore a black camisole underneath with a built in “shelf bra” and just tucked the pump inside. So there you have it - next time you’ve got a form fitting but chunky cowl neck, don’t dismay!

Winter is upon us, and that means it’s time for wool! Wool coats, wool skirts - you name it! This red wool skirt from Ann Taylor Loft has been one of my favorite winter staples for the past few years. The pleat in the front makes the skirt flare ever so slightly, and the vibrant color just makes me happy. To brave the winter cold in San Francisco, I paired it with knee high boots and black tights, but what really kept me warm is the scarf.

I wore the pump on the under arm holster around my waist. I’ve mentioned before that this design, while clever, just doesn’t work for me unless I wear baggy sweatshirts. Luckily it fits around my waist and is a great option when wearing dresses and skirts.

Last weekend was my husband’s birthday and we went out for a nice dinner and then to Bollyhood Cafe where he played a show with his band, Musical Mutiny. I was in the mood for a flirty lil outfit: knee high boots, my vintage coach purse, and this fun zebra print Calvin Klein dress (from Marshalls, of course!). And where’s my pump? Well the loose cut of this dress was perfect to wear my pump around my waist using my “under arm holster”. Although the dress isn’t form fitting, I think the print of the material still kept it flattering.

I don’t do malls. I do about 98% of my shopping at Marshalls, and most recently, at small businesses in my neighborhood. But a few months ago, I went to the mall with my girlfriend and she took me to Forever 21. I spent maybe $20 and walked out with five pairs of leggings. I’m hooked. The problem is, when I wear pants, I typically wear my insulin pump around my calf, but with leggings, that just isn’t an option. So the trick is to find the right tunic/sweater/dress.

I figure you can’t go wrong in basic black, and this one is like a slinky sweater, so it had some weight to it that was forgiving when I wore the pump on my bra. Plus, it had some fun accents to break up all that black.

The San Francisco Giants won the 2010 World Series and I wore orange and black all week. (Who knew I had so much orange in my wardrobe??) This dress was uber on sale, and what girl doesn’t need another LBD (little black dress)? I can’t believe I almost put it back on the rack. But after some soul searching, I realized that the design of this dress was perfect for disguising my insulin pump.

It’s all about the design. While the material of this dress is slinky, the ruffles complete hide the bulk of the insulin pump!