11+ Elevated Happy Hour Outfit Ideas For Work & Weekend

Wondering what to wear to happy hour? You’ll love this style guide with tips and both work happy hour outfit ideas and casual happy hour outfit ideas. Look chic and modern for this favorite pastime.

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A woman wearing a colorful tropical flower corset top with ripped black jeans, sunglasses, and gold jewelry

What To Wear To Happy Hour

Who doesn’t love hitting up happy hour at a local bar or restaurant with friends? After a day or week at the office, sometimes a couple cocktails is exactly what you need to unwind.

Or maybe you want to try some drinks at a new spot while on vacation. Either way, you can’t go wrong getting dressed up and grabbing some 2-for-1 cocktails on a night out!

Whether it’s a martini after work or margaritas on vacation, you should wear something that will keep you comfortable but still look chic and tasteful.  We’ve sourced perfect casual happy hour outfits and work happy hour outfit ideas that will make getting ready a breeze.

Casual Happy Hour Outfit Ideas

If you’re looking for casual-chic outfits you can wear on your next night out, these looks below are for you. These outfits are perfect for hitting up a local spot on the weekend or checking out a new bar while out of town!

a cami + heels

A woman going out for happy hour wearing straight-leg blue jeans with a lacy black cami top, a white button-up, and strappy black heels

get the look:

A sexy cami top and heels are a good look for happy hour with friends on the weekend. This combo is tried and true, and we love that it’s easy to pair with other pieces for a refined look. 

To keep it casual, pair these two with jeans and a button-up, or opt for leather pants, pleated trousers, or a midi skirt for an elevated outfit. You can upgrade this look by adding jewelry and a high-end handbag, making it a sexy and feminine outfit that’s still chic and polished. 

the trench coat

A woman wearing blue jeans with a yellow top, a classic long trench coat, black heeled boots, and a red handbag

get the look:

We always adore a good trench coat outfit, and this piece is such an easy way to add a stylish touch to any look. That’s something we love about a trench coat – it pairs well with so many outfits!

Add it to a casual look like this for a refined touch, or pair it with something a little more formal. No matter how you style it, a trench coat will add that something extra to your look and have you ready for happy hour in no time!

casual chic

A woman wearing black pleated pants with an off the shoulder black top, low black heels, and a black clutch

get the look:

We love adding a chic and playful piece to a formal look. This outfit definitely has a business casual feel, but the off-the-shoulders top adds a bold and seductive touch that’s perfect for happy hour. 

Stick with one color or neutrals for an elevated look, or add a vibrant color if you want to go bold. Heels complement this look so well, and anything from slingbacks to pumps to strappy heels would work. 

How should I dress for happy hour?

When dressing for happy hour, business casual outfits, or semi-casual attire is the best choice. Here are some great outfit ideas for your next happy hour:

  • a midi skirt and a blazer with kitten heels
  • tailored shorts and a button-up with sandals
  • a little black dress with a denim jacket and sneakers
  • jeans and a trench coat with heeled boots
  • a mini skirt with boots and a sweater vest
  • black trousers and a tee with a blazer
  • a casual midi dress with heeled sandals
  • a cami top with jeans and heels

go with neutrals

A woman getting ready for happy hour wearing white trousers, a black tank top, white heels, and a black shoulder bag

get the look:

Neutral tones instantly add a chic and elevated feel to any look, making it easy to style simple and comfortable pieces like a tank top and pants. 

This combination is minimal but still looks classy and put together. It’s also easy to pair accessories like heels, a purse, and jewelry with a look like this. You can stick with black and white or add some warm-toned neutrals like beige, cream, or cognac. 

a tropical happy hour

A woman ready for happy hour, wearing a strapless white maxi dress with khaki green sandals and a handbag

get the look:

A strapless white dress screams tropical vacation, and this look is perfect for exactly that! It’s simple but chic and easy to sit back and relax in while sipping delicious cocktails on a summer day or on vacation in a warm destination. 

We love the rich earthy green tones from the purse and sandals; the pop of color is a welcome addition to this look. If green isn’t your thing, don’t worry! You can rock your favorite shades with a white midi dress, so try blue, pink, purple, or red for a fun and vibrant aesthetic. 

boots + a mini skirt

A woman wearing a slitted black mini skirt with a light beige sweater vest and black ankle boots

get the look:

We are in love with the edgy vibes of this simple combo! Boots and a mini skirt are a classic pairing and something that will always be in fashion. 

The black mini skirt has a fun, flirty feel that’s perfect for happy hour, and you can style it in so many ways. A sweater vest is chic and simple, or go for a blouse, a tank top, or even a graphic tee for a bold and youthful look. 

Can you wear sneakers to a happy hour?

Yes, you can wear sneakers to a happy hour! If you are going to a more casual restaurant with a happy hour, sneakers are a stylish choice that will add an effortless laid-back vibe to your outfit. Plus, sneakers are a more comfortable shoe versus heels, so plan to wear them if you will be walking around and checking out more than one spot. 

the little black dress

A woman wearing a black mini dress with a denim jacket, black and white sneakers, and a white crossbody purse

get the look:

Do we even need to explain why the little black dress made the list? This classic piece is known for its ability to be worn anywhere – especially for party outfits!

While you can easily dress an LBD up with heels, it also pairs perfectly with sneakers for a cool, laid-back look. The Vans and denim jacket have a relaxed aesthetic that looks fantastic with a feminine dress like this. Don’t forget to grab a chic handbag and sunglasses before heading out!

patio happy hour

A woman wearing white shorts with a brown belt, a light blue tucked in button-up, with tan sandals and a large tote bag

get the look:

If you plan to hit up happy hour in the spring or summer, this is the look for you! Shorts and a lightweight button-up are perfect for sitting on a patio with a cold strawberry margarita in hand. 

Opt for cotton and linen blends for a breezy and breathable outfit, and pair them with sandals for an effortless look!

Work Happy Hour Outfit Ideas

Planning to hit up happy hour after work? We’ve got looks for that too. These business chic and formal outfits will easily go from the office to a night out, so you can get off work and get straight to having fun!

go monochromatic

A woman wearing a full white outfit consisting of a silk midi skirt, tank top, blazer, strappy heels, and a handbag

get the look:

We are so in love with the clean and classy look of this all-white outfit. It’s tasteful, so you can wear it all day at work, yet stylish enough to finish the night with. 

The blazer definitely adds that professional look, and you can easily take it off or leave it on depending on the aesthetic you want to have during happy hour. We love the feminine look of that gorgeous silk midi skirt, although you can opt for a high-end pair of pleated trousers if that’s more your style. 

What to wear to after work drinks?

If you’re grabbing some drinks after work, you can easily style an outfit that’s formal enough for the office but will still look feminine and chic for your evening. Pair classic work pieces like pleated pants and blazers with casual pieces like a midi skirt or jeans. This will give you the perfect business casual look that you can wear during your workday and to happy hour.

And don’t forget that you can take off layers (such as a blazer or coat) once you go out, so wear a cute blouse underneath so it’s easier to take your outfit from day to night. 

a midi dress + blazer

A woman wearing a black and red floral midi dress with a black blazer, tall black boots, and a yellow and black scarf tied around her neck

get the look:

We’re always fans of a cute floral midi dress, and adding a black blazer instantly elevates this piece for a work happy hour outfit. The tall boots give this outfit serious fall vibes, so you can rock this look if you’ll be going out in chilly weather.

This is a chic office look and carries easily into a work happy hour outfit. Wear loafers to work and switch to boots for happy hour!

clean + classic

A woman wearing wide-leg black trousers with a white button-up tucked in, black heels, a black purse, and sunglasses

get the look:

Trousers and a button-up are an easy combo that’s perfect for work, and this outfit would look gorgeous while out at a bar or restaurant too for a work happy hour outfit.

This classic pairing is easy to put together, and you can go for neutral colors or try a deep green, red, or blue button-up for something a little more vibrant and playful. Add a classy pair of heels and a fashionable purse, and you’re ready for anywhere the day takes you!

jeans + a blazer

A woman wearing relaxed fit dark blue jeans with a white top, a beige blazer, and a beige and black plaid handbag

get the look:

Jeans and a blazer are the perfect work happy hour outfit combo. The heels and blazer elevate this look, so it’s suitable for the office, and the jeans keep it casual enough for a night of cocktails and fun. 

Go for pumps or heeled boots since sandals or sneakers would make this look a little too casual. And you can take off the blazer before going out or leave it on for a chic and polished look. 

What do you wear to a holiday happy hour?

If you’re going to be having cocktails at an office holiday party, you’ll want an outfit that’s fun yet still follows the dress code at your work. 

Pair a stylish top with trousers or a pencil skirt for an easy look. Or you can opt for a midi skirt with a blazer for something that’s got a party feel while still looking formal. Don’t forget to add pieces with playful details, like glitter or lace, to add a fun holiday flair to your outfit. 

holiday happy hour

A woman wearing a black tweed skirt and jacket set with a silk blouse, strappy black heels, and a metallic clutch

get the look:

If you’ll be joining friends and co-workers for a company-hosted cocktail party, a chic formal set like this is the perfect thing to wear!

Strappy heels and a clutch add that playful holiday feel, while the tweed jacket and skirt set keep it professional. We love the feminine look of the skirt, silk blouse, and heels, but you can easily trade the skirt for pants for more coverage. 


Whether going to your favorite bar, a company party, or a warm destination, you’ll want something stylish for happy hour drinks. We hope this style guide has been helpful and that you’ve found the perfect inspiration for your happy hour outfit!


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