Do these require a long break in period, or are ready to wear right out of the box?

These are ready to wear, however, a leather moisturizer will soften them and make the leather more pliable, plus make the shoes (especially the straps) last longer.

I'm wearing an 8.5 wide, what size should i order since this runs large?

What I have done in the past when buying Docs from other shoe retailers is go to the official Doc Martens website and using their (Docs) sizing chart and measure my foot. That has been the best for me. Docs are well known to be very deep shoes/boots inside and wider than other brands of shoes. I often have to add shoe pad inserts to get a better fit even with the correct size. Doc Martens' shoe/boot size chart is not the same as most shoemaker's charts. I am thinking you will need to consider a 7.5 or 8 in Docs. I wear a women's 7 in Docs but all other brands of shoes I wear 8.

Do they look bad after they've been broken in and creased? Or still just as cute?

I’m a server at a restaurant, and I wear these to work quite a bit. I’m running around and pretty hard on my feet. I have yet to even see a crease!

Dr. Martens Women's EvieePlatform

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