Know What You'll Be Doing That Night

It's important to know what you'll be doing that evening. If you're just going to dinner, what you wore to work may be perfectly fine, assuming you're at least in your own clothes and not in scrubs or a uniform, and you didn't go to work in jeans and will be dining at a 5-star restaurant. 

If you don't know what you'll be doing - that is, that your date has planned the evening, and hasn't told you - you can't go wrong with a jacket and trousers for a guy (ready with a tie that you can add, if needed) or an upscale but not over-the-top dress for a gal (ready with some accessories you can add, if you need to dress up your look). Never over-expose the amount of skin you'll be revealing, ladies - in case you find out you're dining with your boyfriend's boss and his wife that evening!

Low-Key Casual Versus Business Casual Versus Upscale - What Works Out On The Town Is Mostly Feeling Fresh

You could be doing any number of things, from going to a sporting event, movie or museum to having drinks and dinner with friends, to having a private evening at a romantic restaurant. What you wore to work that day may or may not be appropriate for your evening out. Let's assume that it is. Can you just go out like you are? Most decidedly not. 

You either need to bring some cosmetics with you or keep them in your desk drawer at your office (or in your locker at the gym, if you're able to pop by after work). And yes, that's for guys too; after all, no one likes the 5 o'clock shadow when they could see a clean shaven face! 

You'll want to freshen up for your date. So even if you're in the same clothes from the day, you won't feel "tired". You'll hopefully wash your face, put on some fresh deodorant and maybe some fragrance and be ready for your second shift - on the town.

 Bag It (That Is, Bring Your Change Of Clothes To Work With You)

You may be at a job that requires a uniform. Obviously, you're not going to your evening out in that. That goes for nurses, medical technologists, police officers, firemen, postal workers, fast food employees, etc. 

You may be at a job where you're in a suit all day, and you're supposed to be going out for a casual evening.  Do you really think taking your tie off is enough, guys? Or ladies, will you really be comfortable in pantyhose and heels?

So the first thing you'll need is either a suit bag and/or a tote. Why? Because you actually may need to bring things with you to change some or all of your clothes at work. 

And if you can, leave the bag there. After all, you don't want to have to carry around your old clothes throughout the evening and call attention to how much trouble you went to for the date. You can leave the bag at work and bring it home tomorrow after a great, comfortably and/or appropriately dressed evening out.