How to Dress Like You Give a Shit

These past few months have definitely been some of the craziest in any of our lifetimes. But there seems to be a light at the end of the tunnel. Businesses are starting to reopen in many parts of the US, and will be reopening soon in many other parts of the country. This is good news for lots of reasons, many of which are far too heavy and political to discuss on this blog. But there’s at least one reason that should get everyone excited that we can definitely discuss on here: the return of dating.

Whether you’re planning to meet up with your latest match from the dating apps or hit up the bars to meet girls, one relatively quick and easy thing you can do to make yourself more attractive to women is to start dressing like you give a shit.

If you’ve never thought much about how you dress, this can be intimidating. I know it was for me. Halfway through college, I was still wearing the same old clothes from high school, when my fashion sense hadn’t evolved beyond a baggy t-shirt and baggy jeans. Or maybe a baggy polo if I was feeling fancy. So when I finally started caring about how I dressed, I fell into it hard. I went through a regrettable period where I straight up stole my style from an H&M catalog. White skinny jeans? Check. Wingtip shoes with no socks? Check. Skinny trench coats? Check.

Thankfully, I found some balance with my sense of style over time. And in preparation for the return of dating, I want to share some tips for how to start dressing like you give a shit.

The Cardinal Rule: It’s All About Fit

Men’s style bloggers and magazines have been saying it for years. The most important thing when it comes to clothes is how well they fit. From what I’ve seen, the problem of guys wearing baggy clothes isn’t as bad as it was 5-10 years ago, but it hasn’t gone away.

Here’s what I mean. A lot of guys out there are consistently wearing clothes a size or two too big. Next time you’re out, take a look at some of the guys around you. Are their shirts poofing out in the back when tucked in? That means the shirt is too big. Are you unable to see the outline of a leg underneath their pants? That means the pants are too big. Does their blazer or suit jacket make them look like a rectangle instead of making their waist look smaller than their shoulders? That means the jacket is too big.

And here’s the thing. If your clothes fit poorly, it doesn’t matter how expensive they are, they’ll still look bad. You can go out and spend all your money on the most expensive designer clothes, and if they’re too big, a guy with well-fitting clothes from Target will look better-dressed than you.

I’ve been talking only about guys who wear clothes that are too big, but the opposite extreme does exist. If your clothes fit you like Spandex, that’s not a good look either. But this isn’t as common, particularly among straight guys who don’t pay much attention to how they dress, so I won’t spend much time talking about it.

So what should you do? The first thing is to learn your size. For shirts and jackets, measure your chest across the nipples. That’s your size for suit jackets, blazers, and dress shirts. Casual button downs and polo shirts will usually just be sized S, M, L, XL, etc. But you can still translate that to your true size. If you’re buying shirts online, the retailer will almost always have a size chart on their website that connects S, M, L sizing to numerical size. And if you’re a young guy without a beer belly, you should probably be buying slim fit shirts. Regular fit shirts are often made to accomodate guys with bigger stomachs and should be avoided by fit dudes.

For pants, measure your waist around the belly button. In theory, that’s your size for pants. But retailers usually don’t label sizes correctly when it comes to pants. They know that a lot of guys want to be thinner than they actually are, so they’ll call pants a size 34 waist when they’re actually made for a guy with a 36 inch waist. So really the only way to know for sure is to try them on. Most pants have three elements of sizing. Two of them, the waist and length, are pretty obvious (for example, pants with a 32×30 size would be 32″ waist and 30″ length). But there’s a third element you’ll have to consider. The width of the pant leg. If you’re on the skinnier side, you’ll probably want to wear slim fit pants. Anything bigger will swallow up your legs. If you’re more muscular, you’ll probably want a straight fit or an athletic fit. Anything smaller will be too tight. You should generally avoid skinny fit or relaxed fit pants as they’re flattering on pretty much no one.

Also, it will be helpful to find a good tailor. Blazers and suit jackets will often have too much room in the back and stomach, even when they fit perfectly in the chest. So you’ll need a tailor to fix this for you. Dress shirts are the same way. To put it simply, a good tailor can make a $20 shirt look like a $120 shirt.

Wardrobe Basics

Don’t make the same mistakes I did. Don’t go out and waste money on white skinny jeans. If you’re starting to build a wardrobe from scratch, you don’t need a ton of money and you don’t even need that many items of clothing. A few hundred dollars and a trip to Target will be enough to get you started. Here’s what I’d recommend buying to start out:

  • Shirts
    • 2-3 casual long-sleeve button downs
      • Gingham pattern (blues, reds, grays)
      • Solid color (pale blue, white)
    • 1-2 polo shirts
      • Solid color (blue, white, gray, black)
    • 1-2 short sleeve button downs (if you live in a hotter climate)
      • Subtle print patterns
    • 1-2 heavier casual long-sleeve button downs (if you live in a colder climate)
      • Flannel or other heavy material
  • Pants
    • 1-2 dark wash blue jeans
    • 1 mid wash blue jeans
    • 1-2 casual chinos
      • Khaki, gray, blue
    • 1-2 pairs of shorts
      • Gray, blue
    • 1-2 casual linen pants (if you live in a hotter climate)
      • Blue, khaki
    • 1-2 corduroys (if you live in a colder climate)
      • Maroon, brown, blue
  • Sweaters
    • 1-2 casual sweaters (if you live in a hotter climate)
      • Solid blue, maroon, gray
      • Patterned
    • 3-4 casual sweaters (if you live in a colder climate)
      • Solid blue, maroon, gray
      • Patterned
  • Outerwear
    • 1 light jacket
      • Windbreaker or bomber style (navy blue, gray, olive green)
    • 1 medium weight jacket
      • Quilted style (navy blue, gray, olive green)
      • Leather with lining (black, brown)
      • Lighter peacoat (navy blue)
    • 1 heavyweight jacket
      • Peacoat (navy blue)
    • 1 very heavyweight jacket (if you live in a colder climate)
      • Parka (navy blue, black)
  • Shoes
    • Casual leather sneakers
    • Leather or suede desert boots
    • Heavier boots (if you live in a colder climate)

This list is exclusively casual because everyone wears casual clothes some of the time. Some readers might work in environments with more formal dress codes, but this list should at least help you on the weekends.

Pay Attention to Colors

If you read through my list of clothes to buy, you probably noticed something. I suggested almost exclusively neutral colors, with maybe a tiny bit of red or maroon mixed in. There’s a reason for that. Neutral colors are super easy to match. You can look great wearing blue jeans, a blue gingham shirt, and a blue jacket. The same can’t be said for red, green, purple, or pretty much any other color.

Personally, I think navy blue is the most versatile of all colors when it comes to men’s style, and therefore should be the most common color in your wardrobe. The truly neutral colors (black, white, gray) come in second place, but in my opinion those colors are still less versatile than navy blue. For example, gray and brown can look dull together and black and brown can clash. But any of those colors would look great with navy blue.

So navy blue, black, white, and gray should compose the vast majority of your wardrobe, with navy blue being the largest component. Reds and maroons should be the next most common color after that. Other colors like green, purple, yellow, and pink can be worn, but in limited doses. A green, orange, or pink Gingham shirt can look great with dark blue jeans, but don’t go out and buy green or orange pants or a solid pink sweater.

Remember Your Grooming

So let’s say you’ve mastered the basics of dressing like you give a shit. You can’t go screw it up with hair that looks like a bird’s nest on your head.

If you’ve never paid much attention to your hair, now’s the time to start. Don’t just go to any barber shop you find. Do some research to find a quality men’s salon in your area and ask the stylist for some recommendations. Once you’ve found someone you like, try to keep going to them for as long as you can.

If your skincare routine involves washing your face with hand soap, stop right now. Get some specialized face soap at the drugstore and ideally some face lotion too. It’ll help your skin look less oily in the short term and keep it looking younger in the long term.

And if you don’t have enough facial hair to pull off the bearded look, shave every day.

Don’t Obsess

When I first started caring about how I dressed, I went overboard. I would wear blue blazers to college parties and my standard colder weather look consisted of a skinny fit trench coat with bright orange lining. So now I want to save you from having to go through that.

For most guys, how you dress shouldn’t be the most important thing about you. If you fall in love with men’s fashion and want to try out all the crazy trends, more power to you. But if you’re like me, you’re improving how you dress as a means to an end. You want more self-confidence, you want to look more mature, and you want to do better with women. None of that requires you to obsess about your fashion choices.

Wear clothes that fit, buy a few versatile pieces, pay attention to your grooming, and go out and have fun.

2 Thoughts

  1. This is a great article man. I’m pretty excited to start saving up and build up a new wardrobe after putting on some muscle.

    Take care.

    1. Thanks for commenting man! Be sure to check out my post on building muscle for tips on that. And don’t hesitate to reach out with any questions. We love to hear from our readers and are here to help.

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