Reddit mentions of Steve Madden Women's Troopa Lace-Up Boot

London fashion is very similar to NYC, I'd say. Lots of black and classic silhouettes with a dash of punk. So if you dress like a typical Brooklyn-er, I'd hazard a guess that what you normally wear will work perfectly! Here's what I'd probably bring:

• Plane outfit: cozy cardigan, comfy top underneath, high rise dark jeans (or leggings if that's your jam), leather jacket, combat boots, possibly a scarf
  
  
• 5 pairs of socks
  
  
• 7 pairs of underwear (better to over-prepare)
  
  
• Minimal sleep outfit (I don't usually wear pajamas, but you're going with a friend, sooo...)
  
  
• One spare bra, preferably one with a different function than the one you wear on the plane (strapless, push-up, bralette, whatever you end up needing)
  
  
• A flannel and/or a chambray button-down
  
  
• 3-4 tops to layer under your flannel/chambray/cardigan
  
  
• Denim skirt (to be paired with tops for more casual evenings out)
  
  
• Black tights (can't hurt)
  
  
• Low block heels (the smaller the heel, the easier to fit in a carry-on. Plus Europeans love goddamned cobblestones.)
  
  
• One all-out going out outfit (I just got this, which just screams London gay bar to me)
  
  
• One spare pair of jeans if you have room
  
  And that's it! I'd make sure everything could be mixed and matched, with the exception of the going out outfit, and you should have more outfits than you even need.