I love men’s clothes. I have since I was a little girl. I don’t think it has anything to do with being queer, but it might. However, I doubt it. Women’s designers just don’t appeal to me as much. As a general rule, and there are exceptions, I do not like women’s clothes because they’re not designed to be inclusive. There’s a certain palate and a certain look, and if you dress outside that image, you’re on your own.
To me, that image is “I’m for sale! Come talk to me!” I find it easier to move in the world if I dress to accentuate my mind instead of my boobs. But don’t get me wrong. I have a great rack. The girls just aren’t the point. I dress so that the world allows me to be married, if that makes any sense. I want to look nice, but I want to look like your friend instead of someone you hit on. However, I was such a shy single person that I dressed like I was married then, too. I kind of was. Having Dana be my best friend and then transition to my wife is unsurprisingly NOT. THAT. DIFFERENT… at least 70% of the time (wink, wink nudge, nudge “know what I mean?”). In short, I don’t dress to impress others, mostly because I don’t have the funds. If I did, though, I think I would look like some version of Dickie Greenleaf from The Talented Mr. Ripley. His style is just formal enough to show up anywhere, with just enough whimsy to make conversation.
Men’s fashion is my favorite way to make conversation with strangers. I see colors and patterns that I love all over the place, and guys aren’t as catty when talking about their clothes as in many of the conversations I’ve had with women. Here’s something you don’t know about your boyfriend, ladies. He really does care how he looks in front of you, but you often steamroll him before he has a chance to explain why he likes the shirt he picked instead of the one you did. Ladies, you know you do it. You pussy whip your boyfriends into being your clothes horses and you don’t even ask if you’re leading him where he wants to go.
Guys don’t see as well in color as women do- I think it has something to do with cones or rods or something (ask a doctor). All men are color blind to the degree that they don’t see as many shades as women. That’s why you can pinpoint espresso, mauve, and cornflower while he just says “brown, pink, and blue.” Men and women don’t dress differently, they have different frames of reference when picking out clothes.
The next time you’re shopping with your boyfriend, stay out of the way and just watch. No matter which shirt he picks, ask him why he likes it. You are free to berate him for his fashion sense in your head, but so help me God, listen to him until your lip is bleeding in anticipation of telling him what’s wrong with his choice.
It’s in those moments that men reveal themselves, and you’ll miss it if you take your eye off the ball.
You’ll stand there while he’s holding a shirt, and sometimes, it’ll just be a shirt. He just likes it, that’s all. But wait for the surprises, like “my grandmother used to have flowers on her window sill, and this shirt reminds me of them.” Men don’t connect to clothes with their eyes, because they don’t see the hues as clearly. They connect to clothes with emotions.
Think of how much it would mean to your boyfriend if you found a way to memorialize his favorite college t-shirt. He remembers that shirt. It carried him through frat parties, video game and Mountain Dew benders, and practicing until his fingers bled for his audition at Juliard. That shirt isn’t just a shirt. It’s a memory.
Every time he puts on that shirt, he stands in the hard-won victory of finishing school.
If you’re really into fashion, you probably think it’s a way to make you look good. Some men, and they are called metrosexuals, agree with you. But for most men, they don’t care as much about advancing forward with their clothes, but remembering the good times they’ve already had.
I feel the same way about my clothes, which is why I’m so happy with Banana Republic, Gap, Old Navy, Express Men, Target, Ross, TJ MAXX, etc. These are the stores that sell classic clothes that never go out of style, so that you can wear them long enough to attach memories to them.
There are only three things which you should absolutely spare no expense:
- Watch
- A man’s watch is his word. As my sister told me, “you should never trust a man that doesn’t wear a nice watch, because it means he doesn’t value time.”
- Shoes
- Shoes are not a one-time purchase. They are a lifetime investment. Spend as much as you can possibly afford on two pairs of leather shoes, one brown and one black. If you can afford shoes in the one to two thousand dollar range, you will never have to buy shoes again in your entire life. Since you’re a man, I know I’ve just said the magic words. Expensive leather shoes gain character over time, and they look better as they wear. Polish them at least once a week to keep the leather pliable and watch the patina develop. On my own leather boots, I alternate between waxing them with brown, black, and cordovan. As the colors have mixed, I’ve just loved my boots even more.
- Bag
- I’m going to stand up for your girlfriend and say that everyone needs a purse. Everyone. You know why? Because if you carry bags of your own, when we pull up to the bar, you won’t ask us to put all your shit in ours. We know you want to be smooth with just an ID and a credit card so that your pockets don’t grow tumors, but we’re not the fucking crap wagons, you know? When you go to buy your bag, spend as much as you can and get leather. Again, you will only have to buy one bag for the entire run of your existence, because if you polish it once a week, a patina will develop on your bag in the same way it does on your shoes. The way my own bag wears, I polish it with cordovan and pink stars are starting to develop in the creases.
If there is a fourth thing, it’s a belt, but it is not in the same league as the other three, because you can get by with a cheap leather belt as long as you change them often enough that they always look new. However, the same thing with shoes and bags also rings true here. If you can afford two leather belts (because polishing them is easier when they’re not reversible- trust me on this one), you’ll also be able to care for it like a child and let it grow with you. I never forget that leather was once alive, and that it needs to be nurtured in its old age.
That makes me think. My bag is named Cassandra now (you’re welcome, Doctor Who nerds).
To go with your classic shoes, belt, and bag, you need a series of button downs ranging from casual to quite formal. If you’re more fashion adventurous, go for it. But very few men escape the natural uniform of shirt, pants, and jacket. My favorite place to get a classic wardrobe is Goodwill. They have plenty of gently used shirts (and some that have never even been worn) for about $7.00 apiece. In my closet right now, I have Eddie Bauer, Van Heusen, Doc Marten, John Fluevog, Tommy Hilfiger, Isaac Mizrahi for Target, Brooks Brothers, London Fog, Armani, Abercrombie & Fitch and the Gap.
It’s all there, but it’s not in plain sight. Guys, you are going to hate this, and I’m pretty sure about it because I do. Think of it as the spoils of war, because it takes intestinal fortitude to stay at Goodwill long enough to find a $700 trench for $24.
If it’s good enough to sell on e-bay, it’s probably good enough to wear on a date.
Words for the ages.
Good luck, guys!


Just a couple of things. A man will also purchase things for reasons of fraternity (a club t-shirt is an example.) A man will also purchase items that link him to his social network and peers (hockey for example). I purchase items that link me to socially minded things like my sling/ messenger bag that I purchased from a woman’s co-operative in Bangladesh. My purchases are meaningful to me and my shoes last a long time. I have many t-shirts that are over 5 years old and I will use them as rags before throwing them away.
So, the article is good and you have many points I like. The girlfriend perspective is interesting. I think it’s in many women’s nature to dress their partners and children. I have had many moments when looking at a baby and thinking “I can only hope no one EVER takes a photo of you looking like this.” Pink and lacey headbands on bald baby girls is just wrong! I then look at the partner and see the same outfit…. reminds me of uptight middle class Desperate Housewives.
If you want to dress men I think you should start and see what happens. You might end up as a couples counselor.
LikeLike
I completely agree with all of your advice, but I would offer a cautionary note on the belts. In my experience, a man’s belt stays the same size over time, but his waistline does not. It can be worthwhile to simply buy a new belt every year or two rather than overinvest in a belt that won’t fit a few years down the road.
LikeLike
Excellent point, Bob. The only thing I would add is that if you buy a middle of the road leather belt and keep it supple, you’ll be able to sell it on E-bay/take it to Buffalo Exchange/etc. and get more money to put toward a new belt. But if the belt has not been well loved, it won’t be worth *anything.* People will buy distressed clothes, but they don’t buy ugly.
LikeLike
One thing I forgot to mention in the article that I should’ve is that Goodwill has an incredible section of leather shoes if you don’t mind cleaning them. I got a pair of $200 Doc Marten sandals there, and a $250 pair of John Fluevog Angels. Angels repel dirt, water, oil and Satan. Indispensable. I know it’s freaky wearing someone else’s shoes, but if you want to look nice, it’s a worthy cause. Shop cheap. Wear expensive.
LikeLike