Stylish Corporate Outfits – Work Trip

I did not realize how difficult it is to get stylish corporate outfits inspiration up until it happened to me. Last month, I was in Boston for a week for a work conference and I wanted to have some fun corporate outfits. Just because you work in finance doesn’t mean that you shouldn’t be stylish. After spending time on Pinterest, TikTok, and even Google, I felt less than inspired. I decided to let the creative juices flow and come up with my own stylish corporate outfits to share with you!

Boston, Massachusetts

Things To Know (before the fun corporate outfits portion)

First off, please keep in mind that in my job, I meet with chief executives, this means that while I can have fun and stylish corporate outfits, I need to maintain a certain level of ‘traditional professionalism’ at work events and conferences. I am also a heavily tattooed woman and I will never not wear a blazer/long sleeves. At the office, I don’t have this rule. However at major conferences, you know it! This is a personal choice – my company does not force me.

This event was also in Boston and it was my first time attending with bank leaders from all four corners of the world. I did my best to make sure my corporate outfits would be respectful to anyone I would meet.

Also, the weather! While I missed the heatwave, Boston summers are no joke and quite humid. I aimed for lots of cotton and/or linen options and tanks under my blazers in order to stay cool. The AC was on full blast at the conference, but still, I did get hot at times and was glad I opted for lightweight options.

I wore my trusty YSL Collège purse for every outfit as well as it does day to night the best and is quite practical. I reviewed this purse a while back if you are interested here.

Finally, it is worth noting that compliments were given over my outfits. While they may have been a bit more conservative than I would have liked, your girl did good! 😉

Arriving Over The Weekend

I arrived in Boston a day early, so I was able to snap a little ‘site seeing’ fit for you.

I had the opening ceremony the following day. First impressions are key and hard to erase. Some of you OG Allure By Tess readers will recognize this phrase as part of my motto from my styling days. This holds true, especially with corporate outfits in business settings.

I opted for a classic Calvin Klein dress (I wanted to wear my blue one, but I don’t own white close-toed heels yet), a cropped white linen blazer, and some classic red bottoms. The key point here is the cropped blazer. I saw a lot of women wearing long blazers with midi dresses and it just made them look boxy, especially if the dress is not fitted. A cropped blazer not only looks stylish, but more importantly, it gives you a waist and the illusion of it being higher than it naturally is. This not only helps gives you an hourglass figure, but also lengthens your silhouette and legs.

Heels wise, I went for a sensable 85mm height. These Louboutins are so comfortable, however I did have an issue with them that I will mention later on.

Day One – Today’s Corporate Outfit Is…

Look, I didn’t come to Boston to play! Day one is always the most important, with most of the conference attendees being present. Naturally, I whipped out my highest quality fit. This was clearly a McQueen peplum blazer kind of day. I save this blazer for special occasions and avoid wearing it at the office unless I have an important client meeting. I paired it with my trusty Twinset cropped trousers (these are comfier than sweats). I love these because they show a bit of ankle which is quite feminine and they have subtle crystal details on the hardware. I finished off this fit with a simple red tank from Zara and the red bottoms.

Sadly, I forgot to take a full-length photo for this fit. It was a busy work day!

The red bottoms were not feeling great that day and the heel cap gave in. This is partially my fault as I made the mistake of walking from the hotel to the conference in them…. Twice… Needless to say, I started switching from flats to heels at the event after that… I don’t fault Louboutin, it is quite common with skinny heels. They are not made for walking 10mns on the concrete. However, feel free to check out my brutally honest review on Louboutin shoes here.

louboutin heels
I’ve had this happen with many heels. Nature of the heel beast!

Corporate Outfits – Day Two

Okay, this may be my favorite fit of the week! I bought this baby blue costume set earlier this year and my only regret is not purchasing it in baby pink as well. This one got a ton of compliments because this shade of blue is not common in the corporate outfits world. While highly professional (I mean, it is a pant suit), the color keeps it fun and stylish.

Nothing like a bathroom selfie!

I paired this fit with a simple white tank and some creme colored block heels. I did end up changing to flats towards the end of the day, but this was due to wearing heels every day for hours on end in the hot Boston heat.

Final Day

I have two outfits for you for the final day.

For the last day of the conference, I went for the navy version of the previous day’s outfit, along with a simple polka dot tank, and the Louboutins. I avoided walking on any hard floors and stuck to carpet. I wanted to wear a pair of 95mm Jimmy Choo pumps, however my feet were not having it at this point so I had to flip back to the Loubs and be very careful of where I stepped and how I walked.

See how snatched my waist looks with the cropped blazer?

For the closing ceremony, I opted for a fitted dress with a cropped blazer and some flat Jimmy Choo Sandals. This was a more casual event, however I like to always stay professional.

Final Thoughts

Overall, I recommend having fun with colors, cuts, and shoes when it comes to stylish corporate outfits. Most of the women at this event that weren’t wearing traditional garments from their home countries opted for very classic fits. Simple black dresses, black pant suits, and little to no pops of color. Shoes were often simple block heels in a neutral color with no hardware. While there is nothing wrong with that, I like to have spicier fits and I am happy with how my outfits ended up!

For the next conference, I believe I will invest in a pair of white heels (probably Loubs again as I never learn my lesson) at a smaller heel height and look out for more colorful pant suits. If that baby pink does not come back in stock, I plan to invest in a beige version.

Outfit Details:

A lot of my pieces are years old and no longer available, while others were just past seasons. I did my best with the links!

Day and Opening Ceremony:

Day One and Two:

Day Three and Closing Ceremony:

Airport Fits (not pictured):

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XO, Tess

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