Hey lonely guy reader!

I got this question at least a few months ago, but I’m just getting around to answering it now. I hope you’re still reading.

It’s awesome that you want to make an effort. I really believe that wearing something you like and feel attractive in can change your mood and consequently your whole day. Here’s what I’d suggest.

Invest in the following:

- a couple of crisp white button downs (like these)

- 5 or 6 patterned shirts (like this, this, and this)

- a couple of semi-skinny black ties (like this)

- a few plain black, white, or colorful tees with the tiniest scoop or v-neck (like this)

- a pair of slim cut suit pants (like this)

- 2 pairs of dark washed jeans that are slim throughout, but not super skinny or tight (like this) or if you must have something a bit looser choose a vintage cut (like this). You don’t have to roll them, but they damn well better fit.

- a zip front hoodie in a color that goes with everything (like this)

- a few cardigan sweaters in navy or black (like this)

- a cotton v neck sweater (like this)

- some suede boots (like these) or cordovan boots (like these) or wing tips (like these). Really almost anything that’s not sneakers. They might not seem super comfortable at first, but try to choose something you can wear every day. Shoes are hard, I know. Think Hemingway. Think old-timey mountain man. Whatever gets you away from the Nikes. 

- a pair of Sperry’s for spring (like these)

If you feel like I’m being too basic here, feel free to step it up with a hooded henley, some grey twill, or a cashmere blazer. 

I stuck with J. Crew because J. Crew does the classics, and does them well. In my opinion, guys get overwhelmed by clothes and fashion and dudes on TV. The role models are few and far between. Obviously, Don Draper is the icon of our time, but you can’t dress like Draper every day. (If you can, call me!)

The biggest mistake guys make in choosing their clothing is buying everything too big. Pro tip: chicks dig your body. We want to see it. We want to see more of it. We want to be able to imagine what you’ll look like when we’re tearing off your shirt. But we don’t need to know the magnitude of your chest hair or the exact measurements of your dick.

So wear the patterned button downs, t-shirts, hoodies, and jeans to class, and save the cardigans, suit pants, and ties for your dates or nights out. Seriously, if you show up to a bar in a shirt and tie (skip the jacket), well fitting pants or jeans, and a nice pair of shoes, you have just exponentially increased the odds that I will be going home with you.

I hope that helped! A well-dressed man is a rare and wonderful thing. You don’t even have to go in the store. Buy it all online. Buy a couple of sizes. Have a female friend handy when you try things on (sizing can be tricky! you need an outsider’s perspective). Choose soft, natural materials. You are so hot right now.

And for the love of god, don’t forget to match your sock color to your shoes.