Poll: How do you handle the day to night transition?

A few weeks ago on Project Runway the contestants had to design a look to take Brooke Shields’ character on Lipstick Jungle from “day to evening” in a single look. We wanted to scream at the television — we’ve never bought into the idea that women want to wear their office garb out for the evening.  Every time we see an outfit that’s supposed to take you from day to night, it doesn’t…  In our experience, if we’re going out on a work night we either need to change into a cocktail dress (to attend a charity event at a museum or something) or to casual-but-sexy wear for a date or a night out with a girlfriend and a hip restaurant.  (“Casual but sexy wear” has meant, for us in the past, either a casual dress or designer denim and a cute top).  And if it’s just a local neighborhood restaurant or someone’s house, who cares enough to change?  In any case, an outfit for work that’s too sexy for day makes us feel uncomfortable, and wearing our work clothes — no matter how “sexy” they are — while out and about just makes us feel drab and boring.  So we’ve always gone the two outfit route.

After Project Runway, though, we started wondering — are we alone in this?  Is everyone else actively looking for seamless day-to-night looks? Please take the poll and then comment away… particularly if you’ve found something that works great for day to night, do tell.


Pictured above: 13th street, originally uploaded by g. rox.


  1. I am totally with you on this. If you can wear clothes to work that can “transition” in to nighttime, you’re probably not in a traditional corporate environment (lucky ducks!).

    I rarely, if ever, go out for a “night on the town” after work. Usually — hopefully — it’s a “night at the gym” and I’ll just change at the gym. I’ll wear my work clothes to a post-work event (like an MCLE or something), and if I am meeting friends for drinks I’ll either bring a change of clothes and change at work, or, if it’s convenient, stop off at home first. (I know that changing at work can be tricky, especially since my firm has a NO JEANS – EVEN CUTE DESIGNER JEANS – EVER rule, but fortunately my office location allows for a quick, and probably unseen, getaway.)

  2. I agree that an outfit that goes from day to night isn’t going to be your first choice for either but it is definitely doable. I think the Delia’s dress you posted in July is the epitome of day to night, esp for a Friday.


    Just take the blazer / cardigan off and switch up the jewelry / shoes!

  3. punk rock tax attorney :

    maybe it’s a psychological thing, but when i’m not at work, i don’t want to be wearing my work clothes. the time i take to change clothes gets my head out of the “work mode.” when i go out wearing what i wore to work, it just feels.. awkward, somehow. of course, i rarely, if ever, do anything after work that would require “higher heels” or “a tighter skirt” — more like chuck taylors and my raggedy old jeans.

  4. punk rock tax attorney — TOTALLY agree with you re: chucks and raggedy jeans, especially if you’re going to a concert. NOTHING kills the “time to rock out and forget about my corporate job” mood faster than trying to rock out in your suit.

    Laur & M in CA – totally agree with you guys too. Re: the Delia’s dress — I think “casual night out” is far easier to do than “dressy night out” — that just requires total change of clothes!

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