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My Jeans, Your Life: 7 Lessons Learned from Buying Pants

I bought new pants last week.

And the award for the most exciting opening line to a blog post is…

Jeans are a big deal to me. I’ve never associated jeans with comfort. When I was younger, I was a sweatpants kid (and I looked as awesome as I felt). Being fidgety on a near-constant basis to this day, tight jeans scared the crap out of me.

I want room to breathe and sit comfortably. So I’ve always erred on the side of baggy jeans. This isn’t for styles’ sake – it’s for comfort.

But an experience changed my mind and finally brought me into the era of well-fitting jeans. As I thought about it, there were a lot of parallels between going through the jeans-buying experience and life.

Yup, I’m going for it…

1. Notice the warning signs.

I bought jeans last year, and after one trip to Europe that included a crap-ton of walking, the bottoms of all three pairs of jeans were shredded and full of holes. Because they were longer, and I was wearing low shoes, the bottoms would slip over my heel and I would walk on them.

So not only did this damage and completely ruin the pants, but it also made walking incredibly uncomfortable. I spent most of the trip tugging at my pant legs to pull the jeans off my heels, which I’m sure made me look like a normal American tourist.

Hey, that’s a warning sign, isn’t it? Pants aren’t supposed to fit like that. So I already knew that something was wrong.

Is there something going on in your life that has more warning signs than you care to admit? Maybe it’s a relationship, or your job, or something you’re working on. Whatever it is, pay attention. These aren’t just random things that are happening – they’re the direct result of something. So whether you need to listen to your significant other a little more, or you just need to listen to your body, open your ears.

2. Stop settling for the garbage quick-fix.

Prior to last week, my jeans-buying experience would go like this: I’m getting things at Target. I need jeans. I buy jeans at Target based on the price tag and whether or not they feel comfortable. Two trips to the dressing room – max. I have places to be.

It was no coincidence that my jeans fit improperly. I was buying them based on convenience. My problem was having pants that weren’t lasting or fitting right. My solution was to find the quickest, cheapest route out of there.

A lot of times, when we have problems, we settle for a crappy solution just because it’s there. But that’s not the way to do it, at all. You’re going to leave yourself less-than-happy, and you will most likely spend more money in the process. Hey, if I had bought good jeans, they could last me a couple years at least. Instead, I was buying cheap jeans every year at $18.99 a pair, which was much more expensive.

3. Sometimes, it takes a fresh perspective.

I was never really all that oblivious to my jeans problem, but I didn’t spend too much time thinking about it. I just figured it was something I just had to deal with.

Then, there was the photo shoot.

Our good friend Andy (who was our wedding photographer and has done nearly every photo shoot I’ve been in because he’s awesome) gave my wife and I a very fun photo shoot before we left for Europe. We went to a park on a blustery fall day in October. We ran around, played tag, looked lovingly in each others’ eyes, and had a great time.

When we got the photos, one stood out in particular. It was a full-body shot of the two of us standing at the top of a hill, with the wind blowing us around. My jeans were flapping in the wind like the American flag atop a flagpole. You can literally see the outlines of my legs on one side and the wrinkled flaps of the pants on the other side.

I was embarrassed, and I’m not really a vain guy. I knew my jeans didn’t fit right, but I had no idea just how bad they were!

Even if you don’t think you have a problem, it would do you well to find a different perspective. Look at it through someone else’s eyes, and you might be surprised at the severity of your problem, even if you don’t think you have one.

4. Don’t be afraid to ask for help.

Finding new jeans was going to be a challenge for me, so I reached out to the Art of Manliness community for guidance – where they bought their jeans, etc. I got some great feedback on the Levi 501 brand, which I had heard were a solid pair of jeans.

There are people around you who can help you, if you let them. Whether it’s family, friends, or even an online community, there’s nothing wrong with asking for a little guidance. It can save you a lot of time.

5. Prioritize your time to find new solutions.

One problem in my jeans-buying process was my approach – the “I’m at Target, so I should buy jeans while I’m here” thinking process. Instead, I needed to go to different stores, try on different jeans, and make the trip about that singular goal.

After searching around, I found that Kohl’s was carrying the Levi 501 jeans. So, when I finished work a little early one day, I took about half an hour or so to go up to Kohl’s and try on jeans. I tried on 6-8 different pairs until I found the right fit and look.

I made finding the right solution a priority. It took a little bit of a time investment, but by making 3 trips to the dressing room, I knew that me just guessing was going to turn out poorly.

How often do we fly blind when working on our problems? We just assume we know what the answer is, and we do ourselves a disservice in the process. Devote a little time to trying out different solutions. Don’t give up until you find one that works. And when you do…

6. Evaluate your options.

So that’s it, right? I found jeans at Kohl’s that I like, and the end?


I looked at the price tag: $58.99. Now, I understand I have to pay for quality, but I was really shooting for the $40ish range. Sixty bucks for jeans was a little richer than I was comfortable with.

But wouldn’t you know it, Amazon has Levi 501 jeans, and they’re Prime eligible. That means I could order them online (in almost any color I want), in my size, and have them at my doorstep in two days! And the price on Amazon? $42.99. Now that’s a little more like it! Just by looking around at my options, I saved $16. And, now when I want more jeans, I can just buy them at my desk.

Once you’ve found a solution that works, make sure that it’s the most efficient way of doing it. You never know when you can find a better way to get the same result.

7. Spend a few bucks already.

At the core of my problem with jeans was money. As a broke guy, I was always looking for the cheap or free solutions. A few years ago, I’d never spend $40 on a pair of jeans. But now, I don’t think I’ll ever spend less, unless this brand goes on sale.

Buy the app. Get a copy of that book. Grab the gadget that will help. Whatever your goal is, don’t be afraid to invest a little into it. The added bonus is that investing in something strengthens your commitment to it. You’ll prioritize a quality solution when you have put a few dollars into it.

goals, lists, money, shopping, solutions