Thanks, I’m glad you’re liking the blog.
In regards to having an T-shirt under your dress shirt, I think the mistake a lot of people make is going with a crewneck instead of a v-neck. A v-neck will manage to hide better when you’ve undone the top button of your dress shirt. That’s what I wear and I usually buy something cheap from J.C.Penney on sale (if you sign up for their email list you’ll get tons of free shipping or sale notices and then you can just buy a bunch in bulk). Some people prefer to go with some more expensive undershirts that wick sweat away, but I’d say unless you live in a really humid climate (or are rich) then just stick with T-shirts that you can get cheap. I use the Stafford Essentials line because they offer their shirts in a “tall” sizing, so that means it’ll stay tucked in, as these shirts tend to shrink with multiple washings (plus, I’m kinda tall).
Still, the reason why I say that people should wear a tie and jacket is that it’ll really help improve your appearance. If you wear a jacket, it’ll slim your figure (provided it fits properly). If you wear a tie, it’ll keep your collar upright under a jacket. I find that unless I’m wearing a really stiff collared shirt or one with a button-down collar, then it risks “slouching” under the jacket when I wear it.
I get that some people have apprehensions about wearing a jacket and being “too dressed up” at their job. But I’d say you don’t have to wear a worsted wool blazer or something as “sharp” looking. An easy solution would be to turn toward cotton chino jackets with some distressing or washed fabric. This is inherently more casual and layers nicely across the seasons. Lands’ End, J.Crew, Rugby, L.L.Bean Signature and even Brooks Brothers offer such coats (and obviously, you can buy more expensive options). A linen jacket in the summer can look appropriately casual and rumpled — get a jacket with functioning buttons and roll the sleeves up. And in the winter you can go with a thornproof tweed jacket, just add some leather patches on the elbows for a more casual look.
If people ask why you’re wearing a jacket, just use an excuse. Tell them your wife/girlfriend really likes how you look in it and that you do as well. Or say that you like having all the pockets to carry your phone, wallet, pen, knife, chapstick, moleskine notebook and handgun (j/k). Do this for a week or two and people never bring it up again.
If you’re still not sure about the jacket, then consider sweater vests, cardigans or waistcoats. All of these will hide blousing on our shirts and suppress your midsection a bit while adding a layered look. Just get a handful of ones in different weights for each season and you’re set.
If you’re budget’s thin, hit up thrift stores, eBay, Etsy and sign up for email lists so you can get discounts at places like Lands’ End (and L.E. Canvas), which has a ton of discounts on the basics. Keep your eyes peeled at Styleforum Buy & Sell’s classifieds for steals on otherwise expensive stuff. Never pay full price and wait for after season sales to pick up stuff at a discount (usually at around 50-70% off retail).
I will note that at my office, I’m the only one who consistently wears a tie and jacket everyday. I don’t have to do it and I didn’t always do it. I got some crap for it and still get teased about dressing like I’m “Mr. GQ”, but I don’t mind, because I’m dressing for myself. I want to carry myself, purposefully, in this way. It’s something that I enjoy and it gives me a sense of pride everyday knowing I’m carrying myself the best I can.
At the end of the day, my attitude is best summed up by Kanye West: “Can’t tell me nothing”.