A comfy fit and non-fussy details are the point. Limit gold to a man's watch or a bold bracelet to keep it low-key. Dark, lean jeans go from day to night. Paired with a faux-fur shrug, a structured bag seems less uptight.
Denim jeans, J Brand, $178; jbrandjeans.com
Metal watch, Timex, $75; timex.com
Embossed leather bag, Talbots, $199; talbots.com