pants
medium-dark blue jeans – the wardrobe basic, imo. they dress up better than light jeans, but can also easily be worn with a casual button-down or a t-shirt.
flat-front khakis – light or dark khaki, whichever you prefer, but please no pleats. (pleated pants look like the ones on the left in this picture, and flat-front pants like the ones on the right.) khakis are a slight step up from jeans in terms of dressiness, with the advantage of still matching an astonishingly high number of shirt colors.
shorts – casual, comfortable summerwear. I’d start with a pair in black and a pair in khaki. avoid jean shorts. what style of shorts you get depends on personal preference and just how casual you’d like to go. cargo shorts are utilitarian and slightly more suitable for younger butches, I think – in my mind I associate them with high school and college. non-cargo shorts, while still casual by virtue of being shorts, are a little dressier and can be worn with a wider range of shirts. (cargo shorts primarily work with tee shirts.)
shirts
graphic tees – graphic tees are lots of fun, widely available, come in a huge range of sizes, and allow you to express a sense of your own personal style in a way a lot of men’s fashion traditionally hasn’t.
v-neck tees – a little dressier than crew-neck graphic tees, v-neck tees in solid colors are pretty classic and can be worn “up” (with your dark jeans and a blazer) or “down” (with shorts and sandals) with ease. black and grey are good starting colors, and adding in a few jewel or pastel shirts as well gives a lot of versatility.
a white cotton button-down – in my opinion, the white cotton button down is a must-have. for the most versatility, I recommend either a broadcloth or oxford shirt, with a slight personal preference for oxford.
flannel – however you may feel about stereotypes, flannel itself is awesome. it makes great casual wear for fall and winter, comes in a huge range of colors and patterns, and is unbelievably comfortable.
outerwear
navy blazer – worn with your khakis and white button-down, this completes the most formal look available in the basic wardrobe. with your dark jeans and a graphic tee, it makes a more casual outfit look much more intentional and put-together. my preferred blazer-vendor is Uniqlo – they’re much more inexpensive than most, and their men’s sizes run down to an XS, which is something of a rarity.
shoes
brown oxfords/bucks – I’ve had the most luck finding oxfords that look nice, are double-digit rather than triple-digit pricing, and fit well when I’ve shopped at GH Bass in the women’s department. their selection rotates, but there’s a wider range of products at cheaper prices if you look on ebay or other non-direct sources. eastland is a little pricier, but also makes excellent-quality no-frills dress shoes for women.
hi-top converse in a neutral color – my preference is dark grey, but I could imagine owning navy or black converse as well. this is probably my priciest recommendation after the oxfords, but they can last for ages and be worn with almost anything. also, because they’re unisex, it’s much easier to find them in a wide range of sizes than is typical of men’s shoes.
sandals – for wearing with your shorts and tee shirts in the summer! I like the wide straps on men’s rainbows, but havaianas are also an inexpensive, durable option available in a wide range of colors.
accessories
reversible belt – black/brown reversible is the way to go. it saves time, money, and space, and as long as it’s sized right, you can’t tell that it’s reversible. if you’re of smaller height/build, I recommend getting a belt that’s 1″ wide instead of the (admittedly more common) 1.25″ width. you’re the best judge of what works with your body, however, so if the 1″ just looks too thin, size up! (I strongly recommend not going wider than 1.25″, in any event)
a pack of white v-neck undershirts – these are inexpensive and wonderful. wear them as pajamas, or under the button-down and flannel shirts. they keep you from sweating through your shirt as quickly, and in the summer, despite what instinct might suggest, they keep you much cooler. I wish I’d started wearing them years ago.
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what would be in your basic wardrobe? anything you would add? subtract? disagree with? let me know!
if you have questions about what I mean by certain words or phrases, please send me an ask and I’ll be happy to define terms!