21 Pieces You Can Wear to Work — And Then to Date Night

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Work clothes get a bad rap — but sometimes they deserve it. We are definitely over starchy button-up shirts, heavy blazers, uncomfortable pencil skirts and boring kitten heels. We would never wear pieces like that outside of the office. If we had somewhere to go after work, like out on a date, we would 100% bring a change of clothes with us!

We don’t have to dress like that 40 hours a week though. While many offices still have dress codes — or maybe your job requires meeting with clients and looking professional — there are ways to look work-appropriate while still confidently feeling like yourself. Some pieces can be totally pretty and romantic too. We’ve picked out 21 work-to-date-night pieces you may want to add to your closet ASAP!


1. Our Absolute Favorite: The fluttery sleeves on this Neineiwu top are beautifully romantic, but the overall look is still modest and office-friendly!

2. We Also Love: This floral Mango button-up from The Yes would look equally cute tucked into work slacks as it would into a mini skirt!

3. We Can’t Forget: This linen-blend Minibee top proves that some white button-ups can be comfy and flirty too!


4. Our Absolute Favorite: This drapey, longline Romwe blazer will add some flow to your look. We’re already picturing it over a little black dress!

5. We Also Love: A boyfriend blazer like this Vetinee jacket is very trendy right now and can work for the office, a restaurant or even casual streetwear!

6. We Can’t Forget: Come fall, make this long Anne Klein jacket a daily staple — and a daily way to catch compliments!


7. Our Absolute Favorite: Comfy, versatile, professional, fun — we’re talking about Everlane’s The Easy Pant!

8. We Also Love: These Tronjori palazzo trousers will work with any office top, and at night you can wear them the way you could a maxi skirt!

9. We Can’t Forget: These ASTR The Label pants from The Yes have a sparkling sheen that can be made work-friendly with simple, chic pieces and layering. But at night, let them shine to the fullest extent!


10. Our Absolute Favorite: We can easily see this patterned TEMOFON dress with a blazer and flats, but we can just as easily see it with heels and a sparkling hair accessory!

11. We Also Love: Go designer with this Diane von Furstenberg dress, featuring a work-friendly silhouette but romantic red and pink colors. Button or unbutton accordingly!

12. We Can’t Forget: Lark & Ro has some of our favorite work-to-play pieces, and this wrap-style dress is no exception!


13. Our Absolute Favorite: Midi skirts are great because they’re very easy to dress up or down. Take this top-rated dotted Exlura skirt, for example!

14. We Also Love: This pleated Kate Kasin skirt will have you kissing tight pencil skirts goodbye!

15. We Can’t Forget: Sleek, silky and gorgeous on everyone, this The Drop skirt is a can’t-miss for Us!


16. Our Absolute Favorite: This belted Happy Sailed jumpsuit‘s round neckline keeps it work-appropriate, but the flowy top is so beautiful!

17. We Also Love: This adorable Amazon Essentials jumpsuit rides the line between dressy and casual, making it perfect for business casual offices or for a date night at an arcade or park, perhaps!

18. We Can’t Forget: This Max Studio jumpsuit is so flattering!


19. Our Absolute Favorite: This is where block heels can really shine. You can’t go wrong with these bestselling nude Steve Madden heels from Zappos!

20. We Also Love: The Day Glove flat from Everlane is simply a wear-anywhere type of shoe you’ll never want to take off!

21. We Can’t Forget: These mule sandals by The Drop will go with just about everything in your wardrobe!

21 Fall Jackets to Prepare You for the Start of the Season

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