Getting dressed for your job in the summer
Charisma-maxxing casual outfits at the office, wardrobe versatility, juggling outfits for the hot day and the air conditioned office, and outfit ideas that you can recreate yourself.
It’s been exactly a year since we last spoke about summer outfits at the office — highly recommend you read this last edition I wrote because there’s still a lot of great knowledge that’s relevant a year later — but I figured we’re due for a wardrobe refresh.
We all have different jobs that allow us to push the boundaries of what we can and can’t wear to the office. For some, there’s no escaping the suit in the summer, maybe you have casual fridays where you can get a fit off, but that’s the extent of it.
Before going full-time with this blog, I used to have office jobs that had me wearing suits daily and jobs that let me dress casually. If I had to pick, the casual dress code is obviously better, but in a way, it does become slightly harder to navigate what to actually wear to work — if you’re stuck in a uniform or a suit then your answer is pretty clear.
In today’s letter we’re going to focus on getting dressed for your low-key office job that doesn’t have a strict dress code, we’ll explore how to charisma-maxx by dressing less formally but still having that presentation factor, maximizing wardrobe versatility, juggling fits that work in the heat and an ice cold office, and outfit ideas that you can recreate yourself.
Whether you’re a seasoned office veteran or starting your first job that offers free matcha on Friday’s, you have to come correct with your fits, because a good fit = good productivity. On top of that, a fit that you enjoy wearing will at least help you temporarily forget about the fact that you’re probably at a job you don’t really want to be at right now.
When I was in my casual 9-5 era I was maximizing versatility within my wardrobe. I was buying clothes that were acceptable at the office while still remaining casual enough to wear outside of work without coming off like I was trying too hard. I wasn’t making crazy money, so having stuff that I could wear in all aspects of life was really helpful on the wallet.

The name of the game is Versatility — above are 6 quick outfits I made using the same 9 items. Wear these to your creative director ahh job or casually to dinner or on the weekend. Point is, don’t group your clothes into specific life categories. Clothes are clothes and should just be that. Shop smart and buy stuff that you like so much you naturally want to wear them outside of work.
Now, you might be thinking this is too casual, or jeans to the office? I can’t do that. But I’m here to tell you that you can, you just need to do it at a high enough level mixed with a little bit of charisma that lets you get away with what you wearing because you look good and presentable. It’s that bit of confidence that’s rooted in “I’m doing this because I can” that will get you to places you’ve never been before.
Also, we have to break down the walls of the office dress code because I think that concept is stupid in general — my past suit and tie job wasn’t fun to dress for but we did have casual Fridays where I slowly started pushing the needle on what was acceptable or not. My charisma helped my coworkers accept my wild fashion choices with time, which subconsciously had an effect on the entire office because I noticed my coworkers started getting slightly more casual with their outfits themselves.

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If you’re new to the whole office job thing, maybe you have your first internship coming up in the fall, then there are some tips you can follow to make getting dressed for work a little bit easier:
Button-ups are king: Feel like this one is pretty self explanatory. This classic garment is perfect for any office situation that you can make instantly casual with a simple unbuttoning. One tip that I will suggest is to look for smaller sized collars on shirts in general. These tend to be more casual leaning while still being perfect for the office.
Create a good foundation: Once you start getting comfortable at work then you’ll realize you can take off your button up or sweater and just rock a tee by the end of the afternoon. If that’s the case, then make sure you have crisp t-shirts that still keep a well balanced presentation throughout your outfit. Nothing sloppy, make sure you steam your stuff. I wrote a guide on how to buy good basics here to get yourself started.
Get yourself some pants that fit: it doesn’t matter what the dress code is, you are allowed to wear pants that supposed to fit you right. None of that ending at the ankle or skinny pants bullsh*t. I worked in finance for a few years and never once felt like I needed to wear pants like this:




