After Work Drinks Outfits

So, here we are, on the cusp of summer, most of us are able to go out again and work in the office, which beckons this blog post all about after work drinks outfits! Most of us are feeling a severe lack of socialization and we get giddy at the thought of going out again and grabbing food and/or drinks with friends! However, there has been an epidemic of sweats. I mean, only a third of our bodies are shown on Zoom, if that… Nobody’s gonna know! It may take us a few tries to get back into the groove of styling ourselves, but I thought I’d give you a bit of an edge by showing you three easy looks that you can take from your desk to after work drinks. Whether it’s with colleagues, friends, or a significant other, I got you!

After work drinks: pantsuit

The classic pantsuit: this was my go-to at my corporate job before I went down the entrepreneur route. During the day, it’s pretty simple. Pick a nice pair of trousers (I went for a paperbag style here) with a matching blazer, add a simple tank with some neutral pumps and you’re golden. The perfect boss babe!

works to drinks outfit

Now, we have a couple different options to jazz this up for after work drinks. The route I decided on was switching out the tank for a basic bra top (which pairs PERFECTLY with a high waisted trouser as it doesn’t show too much skin) and switching to a cooler pair of pumps. To be honest, you could even keep your work pumps depending on the style. A less ‘risky’ look would be changing the blazer for an edgy leather jacket and keeping the tank under it. For extra style points, I recommend draping the leather jacket over your shoulders instead of actually wearing it. πŸ™‚

drinks outfit
Low key OBSESSED with this look!

The Look:

After work drinks: with a dress

Personally, I think a dress is the easiest way to transform a work outfit into a proper after work drinks look. You typically don’t need to bring many accessories to spice it up and you can even get away with a ‘sexier’ dress thanks to a blazer which keeps you covered during your 9:00-5:00!

slip dress outfit
I was going for a power stance like Wonder Woman… I tried…

For this look, I chose a sexy slip dress. We all know that it’s perfect for the evening, but what about during the work day? Simple! Just pop a structured blazer on over top of it (and keep it closed), add either basic pumps or a smart pair of flats, a watch, and you’re ready for that important meeting. Of course, you don’t have to go for a slip dress, but man, those things are SO comfortable and elegant.

slip dress styling

For after work drinks, remove the blazer, change the watch for a cute bracelet or two, add a belt (you can even shorten the slip dress a bit by using my belt trick here), and switch out your day time shoes for a pair of sleek heels. Plexiglass pumps are a great option here as they lengthen your leg and give you a more flattering silhouette.

The Look:

After work drinks: business casual

If your work is more relaxed or has a ‘casual Fridays’ rule like mine did, then here is what you can do. Opt for a pair of black jeans (or white for the summer!), pair it with a higher quality button-down shirt tucked into your pants (full or French tuck), and finish the look off with some white fashion sneakers, flats, or basic pumps depending on your personal preference. Make sure to accessorize with a nice belt, too. This style still makes you look put together and typically, you end up being one of the better dressed employees which is a very nice bonus. Dress for the job you want, not the job you have, you know? However, it’s still very comfortable and SO easy to turn into something more ‘drink appropriate’. To be honest with you, I tend to wear variations of this look out on the town quite often.

business casual outfit

Now for those drinks, we want to unbutton one or two buttons at the top based on your level of comfort and unbutton two at the bottom. With the ends, go ahead and tie it into a neat little knot for a cute, cropped effect. Roll up those sleeves and make sure to have either bracelets and/or rings to accessorize. For the jeans, cuff them up a bit and add some nicer flats or a heeled sandal.

office to drinks

The Look:

Final Thoughts

The key to turning a desk look into an after work drinks outfit is to plan ahead. If you know you’re going to grab drinks with colleagues Friday after work, don’t wear something that you can’t easily convert into a more ‘evening-ish’ style. Ideally, you don’t want to pack a whole outfit with you because changing in the dirty bathroom or your car just isn’t a good time. In a perfect world, a different pair of shoes and perhaps a jacket to change into is excellent! Here are a couple other things you can consider to help change that look quickly.

  • Makeup! I don’t wear a lot of make-up in general, but when I had after work plans, I’d always bring a liquid eyeliner with me and/or a bold lipstick. This can quickly change your outfit’s whole vibe. You can actually keep these items in your purse at all times in case a surprise outing happens and you didn’t have time to prep a versatile look.
  • Pay attention to your hair. Typically, having your hair down gives a more relaxed, after work drinks vibe than a tight bun. On the flip side, if your hair is up, undo it and throw it back into that bun/pony and make it a little messier and more relaxed.
  • Accessorize. What’s great about accessories is they don’t take up much space and help transform your look. You can easily toss some jewelry in your bag to put on later. Adding some gold hoops or a drop necklace can help give your look a different vibe.

Which after work drinks outfit was your favorite? Let me know down in the comments below!


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Outfit Details:
Pantsuit Outfit:
Blazer: Express (here)
Pants: Express (here)
Tank: Express (similar here)
Heels: Versace (similar here)
Bra: Calvin Klein (here)
Heels: Mango (here)
Necklace: APM Monaco (here)
Purse: YSL (here)
Dress Outfit:
Dress: Lilysilk (here)
Blazer: Express (here)
Watch: Bulova (similar here)
Flats: Chanel
Belt: Tommy Hilfiger (similar here)
Purse: Jacquemus (here)
Heels: Gianvito Rossi (here)
Bracelet: Valentino (here)
Necklace: Vivienne Westwood (similar here)
Business Casual Outfit:
Top: Lilysilk (here)
Pants: Mango (here)
Belt: Gucci (here)
Heels: Valentino (here)
Heels: Aquazzura (similar here)

XO, Tess

**Some of the above links are affiliate links, which means I get a small commission if you buy something using my link. You don’t have to use them if you’d prefer not to. You do NOT get charged extra for using the above links.


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