What to Wear If You’re Going on a Date Straight from Work This Fall

Going on a date straight from work outfit

I know I’ve mentioned this before… but I’m single. I go on dates. A lot of dates actually. But idk if it’s due to the fact that I go on some of the most hilariously bad dates ever. Or to the fact that I talk with my hands and may or may not have wounded a date or two with my favorite ring (whoops). Or to the fact that I’m just a weird human…. but single I am.

As I am now back in the working world (at least for the next two weeks), I’ve frequently found myself going on a date straight from work. And when you get off work at 7PM and your date starts at 7PM, you typically don’t have time to change into a preplanned outfit. Or at all. Or even fluff your hair into something that isn’t the saddest hairstyle in the history of corporate America. Hello, my life.

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What I’m Wearing:

Sweater: Caslon (currently $45.90, will be $69) / Skirt: Halogen (currently $45.90, will be $75)
Boots: Tory Burch (currently $299.90, will be $498) / Bag: Brahmin (currently $249.90, will be $375)
Earrings: Amazon / Crown Ring: BaubleBar / Signet Ring: BaubleBar

When you’re going on a date straight from work, you want to wear an outfit that is cute, comfortable, and yet somehow also corporate. That means modest (which is tough… especially since date looks are usually synonymous with showing lots of skin!).

I like this look because a) it’s completely on sale and b) it’s the ideal look for a fall, casual date night. Especially if your work is more casual / business casual than business professional. It’s modest and conservative while still being somewhat flirty. ALSO this sweater is WICKED SOFT.

Yes, I did just say wicked. It happened. It was weird. No, I’m not from Boston. Let’s not dwell on it.

But really though: figuring out how to dress for going on a date straight from work is hard. And yet it is still somehow the least challenging part of a date. There’s also how to act (sure, “act like yourself” is great advice… But I enjoy randomly bursting into song like a Disney princess… are you recommending I throw that one out there on date numero uno?). There are the awkward hellos (do you hug? Just a handshake? Cheek-kiss like you’re European?) and the awkward goodbyes (you say goodbye only to realize that you did so preemptively since you parked right next to each other and thus have to do your awkward goodbye all over again). THERE’S SO MUCH TO CONSIDER.

So… umm… I rounded up a few of my favorite dating tips to make your life slightly less awkward. Get excited.

My Tips for When You’re Going on a Date Straight from Work:
  1. Don’t take your day with you. Sometimes you’ve had a crap day at work. We’ve all been there. Do what you need to do to leave your worries at the door so you can focus on being yourself on your date. If I’m going on a date straight from work, I always call a friend to get the venting over with before the date starts. So then I can just focus on being my normal, weird AF self.
  2. Bring a toothbrush. I can’t tell you how many times I’ve had something stuck in my teeth literally all day and nobody told me. And then I show up to my date, flashing the biggest grin, and my date’s like “uhhhhh…. you have something in your teeth?” And I just want to drop dead. Right there. So word from the wise: brush your teeth before you leave the office. I’d even recommend throwing some floss in your bag. You know, just in case.
  3. If it’s a weeknight, end the date at a reasonable hour. Sometimes you meet somebody and have a great conversation and end up talking for hours. But don’t let that go into the wee hours of the morning – you’ll be absolutely miserable at work the next day, your performance will show it, and it’s not worth it. I have a rule that I end all weeknight dates by 10:30PM. That gives me enough time to get home and get at least 7 hours of sleep before I wake up to workout at 6AM. Plus, that usually leads to a date #2.
  4. Finally, if you wear makeup, throw some makeup in your bag so you can freshen up your face after work. You don’t need to do the full routine (unless you want to!). I just do some touchups with my eyelash curler, my favorite mascara, pressed powder, and some lipstick (or even chapstick). Easy, simple, and under five minutes.

Do you have any great tips for what to wear (or what to do!) if you’re going on a date straight from work? Share them in the comments below!

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