When I was young, I used to conscientiously try to live by the motto “Live with no regrets.” At that time in my life, this generally meant working up the courage to ask a girl out on a date or trying something I had never done before. Of course, the longer I’ve lived, the more complicated life has become and I have–inevitably–made poor choices that I regret. Over the roughly ten years during which I’ve been interested in menswear, I’ve had much the same goal as in my personal life: Try to make intentional choices in purchasing clothing so as to avoid buying items I come to regret.

I’m here to tell you that, sadly, as in normal life, my best intentions haven’t stopped me from making some mistakes. Here are five bad menswear mistakes I’ve made over the years, and the lessons I had to learn the hard (and sometimes pricey) way.

1. Full-price J.Crew flannel plaid shirt.

This was an impulse buy I made one day when my wife and I were shopping for her back in 2010. She had picked out a cute women’s flannel shirt and with the Americana workwear movement in full swing, I was enamored by the idea of getting one, too. I bought one. I wore it to work one day, which at the time I worked part-time in a small print shop as a salesman. My boss asked why I was so dressed down, and told me I wasn’t dressed well enough to see clients that day; instead I’d work in the back of the shop. That confused me—didn’t they know about the heritage movement and Americana and all that? How was this less dressy than a Walmart polo shirt, which would’ve been perfectly acceptable?

Lessons: Never buy anything full-retail at J.Crew. Also, have a pulse on what normal people actually think about clothing.

2. Ultra-slim low-rise J.Crew wool trousers.

Off the rack trousers almost never flatter or fit me well. In my quest for affordable wool trousers that were decent, I went slimmer and slimmer. After all, slim jeans and chinos fit me okay so maybe slim wool trousers would fix my normal fit problems. This pair of trousers was so slim that when I stood up from being seated, I had to pull the hems down off my calves, where they’d be stuck because they were so tight.

Lessons: Good wool trousers need some room to drape. Unlike slim denim or even chinos, they can never look right in a skinny fit. And if your body type allows a high rise without going bespoke, it looks more elegant worn with a jacket, covering up more of your waist below the jacket’s buttoning point.

3. Too-small vintage tweed Brooks Brothers sport coat.

This thing never fit and never had any chance of fitting. But I bought it because the tweed was fantastic. Around this time, I was also itching to try a different tailor in town, and I used this garment as a test for them. It was a disaster. They did awful, amateur work. My normal tailor, bless his heart, didn’t just fix it for me, but made some highly technical adjustments I didn’t think possible that actually made it fit halfway decently. And he didn’t charge me a dime for the work, which he did out of principle. Nonetheless, the cut and style of the jacket just weren’t my taste, and the fit was still not quite right. I sold it off several months later.

Lessons: Don’t try to take an ill-fitting garment and force it to work. If a jacket is tight in the shoulders or chest, let it go. Also, if you’re going to try a new tailor, do it on something with low stakes rather than something requiring a major sartorial surgical intervention.

4. Beautiful Peal & Co. wingtip boots.

I got an absolute killer deal on these at Brooks Brothers a few years ago. They fit fine in the store, so I immediately began wearing them. But within a day I noticed they were tight on my right foot. I tried every trick on YouTube to stretch them out, while still wearing them regularly for a few months. But of course, nothing worked and I reluctantly sold them off because they simply hurt my feet to wear.

Lesson: With shoes and boots, do your due diligence by trying them on at different times of day indoors on carpet for a week or so to assess whether they truly fit.

5. Brown Eidos topcoat that I thought was gray.

I was communicating with one sales guy who sent me pics of the coat, then switched to another guy at the store to complete the purchase. Due to bad photo quality and bad communication, I got a brown coat instead of a gray one. I found out it was brown while I was on the phone about to complete the purchase. I bought it anyway, and wore it for a while. I loved everything about it except the color—I had had my heart set on the gray, and the brown version just didn’t fit my aesthetic. So I reluctantly sold it off. I found out later they did have the gray one after all. And it was actually even still available in my size, but at that point I wasn’t in a position to afford it. It sold out later that season. I am still on the lookout for one in my size, so if you have one, please let me know (see my Styleforum signature for details).

Lessons: Be communicative and ask questions to an irritating and meticulous fault. Also, stick with one sales person through the entire process as much as is within your control to prevent easily avoidable miscommunication.

What about you? What are some of the worst mistakes you’ve made in building your wardrobe and discovering your style? Leave a comment in the Menswear N00b Mistakes and Pitfalls thread!