Internet Archive Book Images/Flickr (PD) | Remix by Jason Reed

6 ways to give yourself an Internet man makeover

I'd been dressing like a graffiti cartoon from 1993 for years. I know there had to be a better way.

Mar 1, 2020, 1:43 am*



Jason Reed

For most of my life, I’ve never known how how clothes were supposed to fit, or that I could even look good in them. I’ve cloaked myself in hoodies and baggy jeans my entire life—almost all in a blue/grey palette, save for the time I branched out and bought an (gasp!) orange hoodie. So what if I looked like a graffiti cartoon from 1993? It’s what I knew.

But one day, the dryer ate three pairs of jeans in one round, two of them being my last ‘good’ pairs. So I had to drag myself to the sixth-largest shopping center in the country to buy a new pair of overpriced dad jeans.

I’m a proud father two times over, but I don’t want any part of the “suburban-Dad-nearing-retirement” look. You can call it normcore all you want but at the end of the day you’re wearing a pair of white Keds and $60 Lee jeans that make it look like you’re wearing an adult diaper.

I needed help. I knew the Internet had to have a better way.

1) Clothes make the man

I decided to sign up for Trunk Club, a startup that matches you with a stylist who picks out 10 days’ worth of clothes for you. The service allowed me to try on everything at home and return what I didn’t like. It’s a bit like the shopping montage sequence in Pretty Woman, but this time it’s Richard Gere’s turn and he doesn’t have to leave the house to buy clothes. Also, he’s not rich.

Jason Reed

I talked on the phone with Stephanie, my stylist, before she sent the first trunk, so she could get a feel for what would best suit me. You can request specific items, or let your stylist fill your trunk and see for yourself what works and what doesn’t. The first trunk came with an email pairing the clothes, suggesting different outfits to try, but subsequent trunks haven’t. Pricing is slightly lower than you can get from buying these items directly, and even lower if you add in the shipping costs. But be prepared to drop a few dimes: It’s not cheap.

One of the advantages of Trunk Club is that it sends you clothes that you never would have picked out for yourself. For instance, I never would have picked up these yellow shorts in the store but damn, they look good with a bunch of my shirts.

Jason Reed

I would have been hard-pressed to try on skinny jeans, even if it were an option in the stores around here. But I trusted Stephanie’s judgment. I now officially have what I like to call “The First Pair Of Pants That Has Ever Looked Right On Me™.” I guard them with my life. Once we dialed in the right size, it was easy to find some nice dress pants as well, so I’m set for a business meeting (should I ever have one in the flesh, that is–I work remotely).

Jason Reed

Granted, the price is about what I’d pay for three pairs of dad jeans, but I’d rather have one pair that I look forward to wearing than three that just take up drawer space while mocking my very existence. I even picked up these suede sneakers by Clae through Trunk Club. I’ve been wearing the same style of chunky black Reeboks for about a decade and to be honest, they look ridiculous because I have really skinny ankles. Shoes that actually fit make a hell of a difference.

Jason Reed

Having assembled a “casual” wardrobe, I decided to enlist the Internet to start looking for dress shirts. I have yet to find the proper fit for a dress shirt because of my quote-unquote “unique” shape—long arms, thick shoulders, skinny neck. When I wear suits, I usually look like I’m wearing my Dad’s hand-me-downs. That’s why I enlisted the help of Proper Cloth.

Jason Reed

Proper Cloth lets you design your shirt and then makes it to order. Basically, it lets you be your own fashion designer for a day. (Careful, though—I spent way too much time playing with different combinations).

The first shirt includes a free alteration, so you can get the measurements dialed in exactly as you like it. It’s a no-brainer, but a pricey no-brainer. A single shirt is going to run you around $125, but solid-color v-neck tees are five for $25. One or two of these dress shirts will get me through the few fancier engagements of the summer.

2) Find your menswear inspiration.

I found all sorts of great men’s fashion posts on Tumblr, but this one really did it. It’s more than a primer on men’s fashion; it also contains information on what to look for in terms of construction, as well as how to care for your purchases. I learned how to revive an older pair of my nice leather shoes with a few minutes of work. Also, who knew there were so many different types of pockets?


3) Get new skivvies

After hearing on the Joe Rogan podcast what the average length of time that men hold onto underwear is—seven years, according to the Rogan podcast—I decided I was in the market for a new pair of underwear as well. Because the lower elastic on my boxer briefs had given up, which made me look like I was wearing a pair of bloomers, I decided to give MeUndies a try. 

Jason Reed

The MeUndies had a pouch in the front. I no longer felt like a defective Ken doll, what with my lack of frontal smoothness, and I didn’t have to commit to wearing bikini briefs or something equally horrible. I thought I looked like a superhero. Plus, they made my wife laugh.


4) Face forward.

My clothing in order, it was time to address my face. My glasses, specifically. The rest will just have to do as is.

I wore the same crap frames for at least two years. I paid something in the neighborhood of $250 the last time I went to America’s Best for frames that I didn’t like. But they were the best of the three options I had, and I held on to them longer than I should have because of the cost.

This was before a good Internet friend turned me on to Warby Parker. Warby Parker lets you pick out five frames to try out at home, for free. I had a new eye exam for $50 at my local Lenscrafters and turned the information over to WP, who then sent me my new goggles a few days later. I spent $100 less this time around for frames I really like.

Jason Reed

5) Get swole 

In my opinion, the Dadbod craze is associated with normcore apparel, so in an attempt to get in shape when my daughter was born, I bought a single 25-lb. kettlebell. I’m not a gym person, so I figured I would follow the Keith Weber Kettlebell Cardio workout at home with my little starter bell.


I took most of my instruction from Pavel Tsatouline’s YouTube videos with help from Reddit’s r/kettlebell community. Two years later, I now have two 55-lb (24 kg) kettlebells from Onnit, plenty for me to hit every muscle (and some I didn’t know I had). My energy level is higher than it’s ever been and I can throw a small cannonball if the situation ever arises.


If you don’t want to look like a flamingo from the waist down, it’s time for some squats. The Runtastic app gives me a metric to work with, tracking how many squats I do. I don’t know if it’s the ability to show off a new personal best on Facebook, or feeling guilty whenever I see a graph of how many days I’ve slacked off, but I started two months ago and I’m a third of the way through my 10k squat challenge. It has a digital voice coaching you to break a new personal record and a tiered program which slowly ramps you up to Joe Rogan levels of pre-workout body weight squats.


Eventually I found my way to Reddit’s r/gainit, where people go for advice about packing on lean weight. I couldn’t believe what I was reading. Some people were advocating “GOMAD”, or “Gallon of milk a day.” But for the most part, it offered solid, common sense advice.  

After a while, I started to wonder what my caloric intake was. My Fitness Pal is a website and app with a calorie tracker, in whichever direction you want your weight to trend. I’ve put on roughly 15 pounds of muscle over the last 6 months. I’m not the Rock, but we all have to start somewhere.


6) Get your beauty sleep

With all that new exercise and proper diet, you’re going to need some rest.

I started tracking my sleep with my phone a couple months ago, and the data it provides is very helpful. The more you use it, the more it learns to predict your best bedtime, sleep length, and wake time. As you can see in the following image, I’m sleeping quite a bit better than I was. Unfortunately, this isn’t a result of merely using the app, but a testament to my physical therapist, who I started seeing about halfway through the graph.

Jason Reed

Was this an overnight process? No. It took time and effort. Was it cheap? Hell, no. I spread these out over the last six months, because I’m a working-class hero like you. But all in all, I spent less than $1000 on everything, and it feels like it was worth it.

I feel better. I look better. I have more energy for work and play than I had five years ago, before my kids were born. I saw things about myself that I wanted to change, and the Internet connected me to people with the right information, and companies with the stuff to make that happen. If you want to improve parts of your life, there are resources available to you to do so.

It’s a brave new world, and for a few bucks and a little sweat you can look the part, all without leaving the house.

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*First Published: Jun 12, 2015, 11:00 am