Night Ripper

Here are some Redwing Beckmans in black in 12d for 85. Would have copped but not my size.

http://beaconscloset.myshopify.com/collections/new-arrivals/products/beckman

they also have a ralph lauren boot in 11 for 85

http://beaconscloset.myshopify.com/collections/gentlemens-shoes/products/lace-up-lo

I'm looking to get a pair of White's SD for this winter. Brown, with leather lining, with all metal eyelets, natural edge and a vibram sole. My only hangup is it seems difficult to find fit pictures of anyone with skinny jeans and SD. I wear skull 5010xx and PBJ 007. Do they look chunky? I have a feeling it might look better than the RW GT which i'm also interested in because of the different toebox.

I will get pictures later but right now my only boots are my clarks beeswax chukkas and some CT chelsea boots I picked up while in London.

Sorry for the stupid question but do mid-length or smaller wallets with snaps wear holes through the back pocket? What about sitting down? Am I missing something stupid?