5 Desk-to-Drinks Outfits for Happy Hour

Cute when you clock in, cute long after you clock out.

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Happy hour outfits - header image

This is a question as old as time, but the answer is ever-changing and always important. Is it really possible to style an outfit for work that looks equally as good for happy hour after?

On one hand, you want to ensure that your outfit is professional and comfortable to wear all day long. However, professional looks are rarely head-turners at happy hour.

The key is to create a cute, yet classy outfit, that is entirely office-appropriate but also easy to manage into laidback evening wear.

This can be done by adding layers that are easy to take off when you’re hanging with friends.

{See related: How to Dress for a Job Interview}

Here are 5 fashion-forward happy hour outfits that will save you time and stress!

Oh My Posh

Here’s a case study in desk-to-drinks layering: a white, button-up blouse is work appropriate and can easily be removed to reveal a lace cami underneath.

While it’s not visible throughout the day, this cami is a solid choice for your night out top, and nobody at work will even know you had it on all day!

These sassy faux leather pants are a statement piece, but with your professional blouse they will be work-appropriate for most jobs.

I styled this look with some simple gold hoops and a small pendant.

These heels are also perfect when you’re looking for comfort all day long.

A Flirty Look

Desk to drinks look 2 - black sleeveless turtleneck, midi skirt with thigh slit, strappy black heels with lucite heel, rose fringe earrings
Products: Top, Skirt, Heels, Earrings

This look has a very fun and playful feel.

The floral pattern of this skirt gives a stark contrast to our sleeveless top, and it breathes life into this look.

I paired these pieces with some adorable strappy heels as well.

To top it all off, I discovered these gorgeous tassel earrings that give the entire outfit an exciting vibe for happy hour.

Also Read: 100 Little Things That Will Make You Happy

Pinstripe Pantsuit

Happy hour outfit 3 - black pinstrip suit with cropped jacket, leopard print heels, gold leopard hoop earrings
Products: Blazer, Pants, Heels, Earrings

Nothing says powerful boss babe the way a pinstripe pantsuit does.

This one can be rocked with a chic, lacy tank top underneath, but this is also a strong outfit for happy hour as it is.

I added some touches of leopard because you can really never go wrong with it.

Personally, I think that this suit makes for an extremely professional office look but something you will not want to take off as you venture into the night.

Go-To Glam Look

Desk to drinks look 4 - black bodycon maxi dress, white vest, pointy-toed pumps, black and gold earrings.
Products: Blazer, Dress, Earrings, Heels

This 80s-inspired happy hour outfit is a fashionista’s dream. The white blazer vest gives this outfit a very professional feel to it.

This maxi dress can be worn all day for work, but would be the talk of the town once you have clocked out.

I incorporated some geometric black earrings into this this outfit because I felt like this look needed something a little extra.

I paired the whole style with these gorgeous shoes that play into the whole black/white vibe.

Not-So-Blue Look

This outfit is probably my all-time favorite fancy work look. It is so fun for the office that you will have heads turning, but also a great outfit for happy hour. Who doesn’t love a blue pantsuit?

I chose a simple, white blouse to allow the light blue pantsuit to shine, as it should.

I paired it with these adorable, ruffle denim heels. The wide pump gives for an insanely comfortable feel throughout your day.

My favorite touch is always going to be the jewelry and these earrings are no exception.

This colorful tasseled pair brings the entire look together and keeps onlookers gazing at the impeccable details of the outfit. They are sweet for a day in the office, but these will truly shine later on in the night.

What do you think of these happy hour outfits?

Let me know what you think of these looks! Do you have a favorite style above? Which one could you see yourself wearing easily from your morning desk to evening drinks?

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