Not sure if I can kill two birds with one stone here. I’ve been thinking about getting simple slip-on shoes for the winter, and now apparently should ease into orthotics. Can those be the same thing? What do you think of these shoes as carriers of orthotics and/or for my style?

QUESTION 1: I know lots of people here wear orthotic insoles; can some of you please help me out? The doc who treated me after I broke my big toe last summer is convinced I need orthotics for fallen arches and bunions. I’d rather focus on healing, but figure it’s worth making sure I have some that will work. Today he lectured me on my black tallish(ish) Redwing boots and metallic floral Chelseas not being appropriate. He also thinks my red ankle boots are too extreme, which made my PT roll her eyes. I’m willing to make a (small) effort to get some shoes the soles will fit into. (I don’t need them all the time—he suggests getting one pair that really works well). Which of these look like good bets for orthotics?

QUESTION 2: I’ve been thinking about how much I missed having simple slip-on shoes last winter—I get so tired of pulling on so many pieces and buckling/zipping/tying things up! I have a bunch of slip-ons in my cart already, so I might combine the purchases, but maybe I should just go ahead with the slip-ons and then let the orthotics be their own thing. Then I can just think about getting some slip-on shoes I like. Which (if any) of these styles look right for me?

IN GENERAL: Can you tell in advance if an orthotic soles will fit into a shoe? Will any of these work? I notice that Angie commented that one of the pairs of shoes in her cold weather picks today fits an orthotic.

NOTEs ON THESE PICKS The first find is from Call it Spring, the brand that made my beloved multi-color loafers with mirrors. Those fit perfectly and lasted forever. I’ve never heard of Darkwood (the Uggs knockoffs) before, and would need encouragement before ordering them. Towards the end are some pairs with closure, which isn't really the remit here, but I think I could slip on the monk strap shoes without unbuckling. About the colors—looking through my finds, I see that it is no fluke that these pale pink ankle boots appeal to me; I’ve been making finds of similarly-colored shoes for years, including considering pink suede Timberlands when we first got here.

Bonus question: do any of them look like me?