While doing the “Previously” posts for this month, I was thinking that the “desk to dinner” transitions one would be a good one to revisit since we have such a bigger community now to discuss.
At the time I wrote the first post, Project Runway had just done a challenge where contestants had to make one outfit that could carry a woman from daytime work to a hot date — and I just remember thinking, well this is just going to result in slutty workwear/frumpy datewear.
My own method has always to just bring an entirely new outfit to wear out and about.
Tonight, for example, I’m going to a fairly fancy party and so I have a dress, my highest, hippest heels, and my trusty black wrap because it’s starting to feel like fall in Manhattan.
Meanwhile, at the office I’m wearing simple black pants, a purple long-sleeved top with ruffles on it, and gray Cole Haan pumps. Heck, I even have a different bra packed for the party tonight.
The only thing I’m planning on wearing the entire day is my jewelry, which admittedly is a bit much for the work outfit (dangly diamond earrings and a right-hand diamond ring, in addition to my regular watch and wedding/engagement ring), but I really dislike throwing good jewelry into a handbag to wear it later.
(Pictured: These are totally not my earrings, but aren’t they pretty? And really, who needs college, grad school, and a nice downpayment for a house when you can have these lovely earrings instead? I always say, if you’re wondering whether you should buy a studio in Manhattan or a pair of earrings, go for the pair of earrings!)
Funny story, though — back when I was dating, I remember going on a first date at a lunch and thinking, well, it would be weird to change into jeans for a lunch date. So I wore what I had worn to the office — black pumps, black sheath dress, and, I think, my pearls — and the guy thought I had gone all out for him (and actually seemed a bit intimidated by that fact).
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Psst: you can sometimes dress up a basic sheath dress with a few great accessories and a change of heels — here are our latest favorite sheath dresses: