I am going to tell you the desperate, maddening, unhappy truth: you should keep all but one or two. Sell the one or two you never wear. Then wait a year and buy one more.
At first glance, I would have chosen the JL. At second glance, however, it seems a bit shorter than the Aero. So in the overall impression but rather the Aero. But since both are good, I would keep both and look which I wear more often.
Of course @ton312 liked this haha
The only edit I would add is….sell them all, buy a few back from the buyer you sold to, sell again, buy back again… of course sell again. Buy something worse, and something better, sell both, swear off leather buy tons of wool….and leather. Sell all, buy Levi’s Sherpa jacket and feel content you’ve won. For 3 minutes…then repeat the entire cycle (and sell the Sherpa).
Kind of hard to say with the shirt untucked. Stylistically, it doesn't appeal to me but that's just personal preference/bias.
I think as soon as you ask yourself whether you should sell something or not, sell it.
Alden 403 Moc Toe Boot - Brown Chromexcel - $680 The classic "Indy" style Alden Boot in the classic Horween brown Chromexcel. 
Grant Stone Diesel Boot Dark Olive Chromexcel - #395 Goodyear welted, Horween Chromexcel, classic good looks. 
Himel Bros. - The Ross Mk. 1 Leather Jacket Classic D-pocket motorcycle/aviator style jacket. 
I like the style, just not sure if this looks too small
Just to confirm, Yes= yes, get rid of?
No, Yes means keep and no means go. The British designs fits you much better than the American one imo.
Ah interesting, I’ve always gravitated towards the American styles, mainly due to it being less structured / less pasting
‘No, yes means keep’ also gave me a chuckle
