Let me preface by saying I struggle to put outfits together....

I have a 5-day urban trip coming up where the weather should be in the 60s and dry. I’m testing out a capsule approach so I only need one bag, but I am struggling to choose a couple of pieces.

So far, i have tops in burgundy, navy and olive, one pullover in grey and an oatmeal open cardigan. One print scarf with the above colors in it, plus a leopard print one. One pair of dark denim and one grey cord. Shoe is a taupe slip on sneaker.

I am stuck on shoes and a jacket. I wanted to take my waxed Barbour jacket (called olive but it’s actually more chocolate brown) because it has inner pocket for my wallet and then I won’t need a handbag. Trouble is, I worry that the brown doesn’t really work colorwise... AND we have one nice dinner thrown in the mix and I worry the jacket is too casual. Also the only shoes I have that could bookend the look are tall Frye riding boots. Again, are they too casual?

My question is: should I stick with the Barbour or find a different topper in the same color palette? Should I throw a blazer and pair of taupe booties in the bag for the dinner?