Business Casual Starter Pack
The weird thing about the military is we kind of pride ourselves on not having to wear fancy clothes or be attuned to meaningless trends.. We are tougher than that. Well guess what, you need to ditch that attitude in the business world. Brand names, trendy clothes and some level of coordinated fashion sense are a necessary evil. Over time, you will start to get into fashion and find that clothes are a way to express yourself and your attitude. Some general guidelines
Start out conservatively, and as you grow into your new style you expand what you are comfortable wearing
Buy nice stuff. It lasts longer, displays class in a quiet manner, and people notice. Dress like you have done this before
Try to not pay full retail for this stuff. Look for sales, outlet malls, holidays etc. TJ Maxx is really great to pick up a lot of this stuff except for the super new brand names and very exclusive brands
Oxford shirts are now appropriate here. In fact, they are one of the primary shirts you will wear. The buttoned down collar lends a quiet confidence and is very versatile
Find some brands you like and identify with. I personally have became very partial to Cole Haan, Barbour, Polo, J-Crew, Bonobos and Lululemon
Dress in a way that makes you feel confident and comfortable.
Bonobos Mens Stretch Washed Chino Pants
Bonobos is one of my favorite brands. My wife introduced to me. Basically they are chinos with some flex in them. Better than regular khakis and more versatile as well. Goes well for business casual or everyday wear. Available in a wide variety of colors. Thick enough to protect you in the cold as well. Can also function as a dual work and play pant. I wear the khaki color.
Lululemon Commission Pant Classic
Hear me out. When most people think of Lululemon they imagine yoga pants, but in recent years they have expanded with a huge selection of offerings for both men and women. My wife recently got me a pair of the commission pants. They are basically dress pants that feel like sweatpants. I got them in blue. LOVE THEM. They are cheaper than regular dress pants and a hell of a lot more comfortable. When I have to go to conferences, travel, work for hours at end at a client site, these bad boys are lifesavers.
Cole Haan Men's Zerogrand Wing Oxford
These dress shoes are hella comfortable. Both light and stylish. They are also super soft out of the box. You could run a marathon in these bad boys. Different colors to suit your preference and style as well. People will notice these when you wear them and be impressed. Hanging out in dress shoes for hours will destroy your feet, so it pays to be as comfortable as possible
ARCTERYX CERIUM LT VEST MEN'S
Super warm and very stylish. It lets people know that you have something that resembles style and taste outside of patagonia. Vest’s in recent years have taken on an almost cult like status in the business world. They have replaced what was sport coats and even suits. The corporate elite love the “midtown” uniform, or basically business slacks/khakis/chinos/jeans with a button down and a vest. So yea, believe it or not you are going to want a vest.
Patagonia Men's Classic Synchilla® Fleece Vest
Collectively referred to as “patagucci” by legions of finance and consulting bros, this vest became so popular with the corporate crowd that patagonia actually prohibited corporate logos from being put on their products. This is the quintessential add on for the true “mid-town” uniform look. It’s honestly a great functional and slim vest. I have my Tepper one that I got when I was at school and throwing it on makes me feel like an evil member of the corporate and social elite. The little red menacing logo on the front looks like you strolled out of an ivy league frat house after railing a huge line of coke and laughing at how rich you are.
ALLBIRDS
Funny story, I went to the park the other days with my kids and wife, and we ran into our neighbors and their friends. All six adults were wearing Allbirds. This fabric makes the shoe strong as leather but breathable. You can wear the shoes without socks if you want, which is perfect for summer. The winter versions are also waterproof and more comfortable than other boots. The shoes are reliably priced $100-$135. I frequently get compliments on my birds at work
Polo Ralph Lauren Classic Fit Mesh Polo Shirt
Can’t go wrong with these bad boys. Available in just about every color you could want, these are classic, understated, and pair well with jeans and chinos. They last a long a time as well. The shirts convey a look of class and privilege and help establish an equal footing when talking to someone. Does that seem insane? That a shirt could convey that? Well trust me it does
Amazon Essentials Men's Regular-Fit Long-Sleeve Gingham Casual Poplin Shirt
Here is a dirty secret about button downs, they are generally over priced. Amazon makes a great line of affordable and easy to wear button downs that get the job done. You could also wear Peter Millar, Jcrew, and Untuck-it. The options for these kinds of shirts have really exploded in the past few years, with startups rapidly disrupting the shirt market. Try to not look a dad. Dress semi cool. Imagine what like a cool late 20’s kid who is sophisticated and knows better than people twice his age.
Men's Casual Belt Super Soft Full Grain Leather Belt - Black, Brown, Tan
For some reason Amazon would not let me display the brown belt of this version. Anyway, for business casual you want to wear a wider belt than what you would wear with a suit. It reflects the more casual nature of the environment. Tighter, more exact clothing generally equals more of a high stakes enivornment. Chill on the belt buckles, just have it be simple. You don’t need to go gucci with these, just get something that looks good and you are comfortable spending.
Apple Watch Series 5 (GPS + Cellular, 40mm) - Space Gray Aluminum Case with Black Sport Band
Apple watches are becoming the go to timepiece for people in both work and business situations. They also convey that you are hip and innovative. I am seeing less and less fancy watches in the overall corporate and mba world. With the work world look becoming more like axe capital in the show billions, it’s becoming increasingly fashionable to tune out old analog technology. It’s amazing that Apple has managed to pull this off. Anyways, yea get an apple watch. It’s ok to have a rubber sport band on these. It shows you work out and people pick up on that. I’m dead serious.
Ray-Ban Wayfarer Sunglasses
Ditch the oakleys and get some ray-bans. You are not a knuckle dragging soldier anymore. The ray ban look implies an attitude of knowing and confidence. Like…JFK. I’ve yet to meet anyone, including drunk idiots, who didn’t manage to have air of respectability applied to them because of this glasses. Also check out Shady Rays. Very cheap but good sunglasses and and two free replacements!
The North Face Men's Apex Canyonwall Vest
An alternative to the patagucci look. Probably more practicable also. Will keep you warm and dry. A big part of living in larger cities is the shitty weather. Having a good vest like this allows you to bear the fall and spring months when there is lots of rain and wind but not a need for a heavy coat. This also doesn’t scream douche, which some of the other vests can. It’s up to you, I’ve accepted who I am.
Shady Rays
My current love. These bad boys are hella awesome. Kinda like the allbirds of sunglasses. They have a super cheap price point at $45 dollars, are polarized, and you get TWO FREE replacements. Available in multiple styles and colors for both men and women.
Barbour Jacket
These jackets are descended from classic jackets waxed hunting jackets in England. Some of them even have a spot to store birds…or ice cold bud lights. If I was going to sneak a beer somewhere, this would be the jacket. The pockets are huge. When we go for walks in Chicago I throw like 4 beers in this bad boy, and I don’t even notice. The jacket is waterproof because its waxed, and also resists the spill of draft bud lights and overpriced ipa’s. While you probably won’t be tromping through the British brush with a 12 gauge and a hunting dog, this will help you survive the perils of everyday in a flat gotham type city. They have a wide variety of jackets, and while expensive, are not as expensive as you think. The jackets are a good departure from boring petticoat styles and generic cold weather jackets.