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Hey everyone. Was down in Key West last friday for work, and while time was minimal I did wear my Cole Haan grey suede shoes a bit around the hotel/etc, and wedge boots on Duval. A pretty basic outfit really, have shown it before.

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This Fri I am heading back, hoping to have more time, and hoping to get a bit more daring. I plan to bring the outfit from my AVI, and wear the boots on the outside of the jeans. Am still trying to decide if I should just go for a gay hotel, or stay at a nicer place off Duval, neither should present any issue as far as safety when wearing heels in public.

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I've limited myself to 3" heels for drives in the car since higher then that I was getting a nerve pain in the back of my right knee. I also plan to bring a pair of black leather pumps from Ash, about a 3" heel, that will be my fall-back if I chicken out or decide the sidewalks in KW are too bad for the higher heel boots.

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Oh well, will be a heel heavy visit as I think I will be able to wear my Nike wedge sneakers while at the jobsite, and plan to have no-non heels with me from check-in at the hotel till work the next morning.

(formerly known as "JimC")

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Shafted: Thanks, I kind of think the jacket is needed to balance out the dramatic look of boots over jeans for me personally, but it's usually too damn hot down here to try. Even in late January it's in the mid 80's :(

(formerly known as "JimC")

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" Thrasher "?!?! As in the skateboard mag? Ya know.. I have a t-shirt somewhere around here that says ' Breeder ' in rainbow-pride colors I should mail ya just to drive tour significant other crazy! :D It appears our styles are very similar. Just ' casual '. -Ilk

REPEATEDLY ARGUMENTATIVE, INSULTING AND RUDE. BANNED FOR LIFE.

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ILK: hehe, well, considering where I got the shirt I doubt it was a skate company, probably skate inspired. I do tend to dress more casual since my b/f will not dress up at all, and it would look odd if I was trying button up shirts, slacks, etc while he was in basket ball shorts and a tshirt.

I had trouble finding clothes I liked when I was a kid, turns out it was not liking any of the options available. A few years ago I went exploring around Miami/Aventura and found clothes I liked at Bloomingdales and Barney's. Problem was the prices were so high I refused to buy most of the stuff I did like. Might be how I got in the habit of hitting the Nordstrom Rack's, Neiman Marcus Last Call, Bloomingdales and Saks outlets now. Does not hurt that they all have a selection of heels, often at great discount. Got nearly 90% off for one pair. I did just get a black pair of the Nike Wedges at 2/3 off at a Nordstroms outlet. Plan to wear those to work today since I am just doing testing and driving.

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The red/black pair I have I wore in TX when staying with my b/f's parents. His mom said they were cute, but I had small feet. hehe

(formerly known as "JimC")

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So far checked in wearing the pumps, currently at dinner in a variation of outfit 2, Cole Haan 4" heels, but will switch back to the 5" Boutique 9 boots to explore the hotel grounds. I do wish these followed my arch a bit better. The street heeling is teaching me what to look for in heels for comfort. Quality is important, fitting the shape of your foot is more so.

(formerly known as "JimC")

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Love the Nikies! I need to find me a pair of the sneaker-wedges. Second outfit is very casual, kinda like something I would be seen wearing out and about. Blend right in.

REPEATEDLY ARGUMENTATIVE, INSULTING AND RUDE. BANNED FOR LIFE.

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