5 Shopping Mistakes and Lessons Learned

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.

jcrew flannel shopping mistakes

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.

jcream slim pants shopping mistakes menswearOff 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.

shopping mistakes menswear brooks brother tweed jacket

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.

shopping mistakes menswear peal co 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.

shopping mistakes menswear eidos grey brown coat

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!

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  1. Reply

    Don C

    January 3, 2018

    Great article. I am learning the ropes and have been all over the place, much to the bemusement of some SF’ers.

    Thankfully, some members are willing to help and once I know my fit, I can have fun on the forums again.

    – DC

  2. Reply

    Gus Walbolt

    January 3, 2018

    Good examples. I would add, that from time-to-time, no matter how much research you do on fit, style and color, there will be some things that just don’t work for you. That will be due to a variety of reasons – your build (some brands will never ever fit me), your complexion (what looks good on the model may not flatter me), mixing with the rest of your wardrobe (Esoteric Japanese with tailored Italian? Hmmm?), etc. If you seek an evolving personal style and wardrobe, you’ll make a few mistakes along the way. There will be a few missed shots so just accept it and move on.

  3. Reply


    January 3, 2018

    what are we comparing “mistakes” to here? Depending on your life or life you need a variety of clothes. I know I do. I cannot wear nice clothes to work, as they might suffer in the environment in which I work. Also “overdressing” is somewhat frowned upon. One simply cannot obsess too much about J Crew purchases from normal lines. I would note Crew has been selling some high end products of late, which must be OK. Shoes that do not fit well, we’ve all got those! No sweat.

  4. Reply

    Fok-Yan Leung

    January 3, 2018

    I like that two of five mistakes were made at J. Crew!

    • Reply

      Charles L.

      January 7, 2018

      Amen to that.

  5. Reply


    January 4, 2018

    I think the Eidos coat was more awesome in brown than grey, alas I wasn’t the one who ordered it 🙂

    • Reply


      January 5, 2018

      LOL it was great. Loved it. But, to quote an old Styfo Luminary, “brown is for farmer.”

  6. Reply


    January 7, 2018

    Interesting article though it raises more questions then answers. For example, most of the stores above will take back merchandise no questions asked. There’s no reason these days to be stuck with something you don’t like. Check the company’s return policy before buying and proceed accordingly.

    Never alter anything unless you’re positive it’s a keeper!

    Also, most of the stores above, especially JCrew, have sales almost every week so buying anything at full price these days is really unnecessary.

    Looking forward to your next article.

  7. Reply


    January 7, 2018

    I think you are bonkers for selling the brown Eidos coat. There is a reason brown is a halcyon throwback and regaining traction – it’s actually classic, looks expensive and warms the skin. As you age, the skin can look dull and while I love grey, it tends to hurry that process. Brown has the benefit of having some red undertones without being red – it can really make you look alive.

    The brown is for country farmers way of thinking is both musty and moot at this point.

    • Reply

      Charles L.

      January 7, 2018

      I agree. What’s wrong with brown? It is less formal than black or grey but manages to keep a bit more character as well, in my opinion. There’s a reason most leather is some sort of brown.

  8. Reply


    January 7, 2018

    I bought a Canali proposta black herringbone Merino sport coat. It was one size too large and a long, when I normally wear a regular. But it was such a beautiful fabric and I have a love of herringbone that I thought it could be tailored to fit. I wore it a couple of times before I realized that it was just too long and trying to have it tailored would just ruin the jacket. Luckily I purchased it at a fraction of its retail price at Filene’s basement so the loss wasn’t too bad. I really love that jacket.

  9. Reply


    January 7, 2018

    It is certainly not for me to tell you how to feel about your clothing, but that tweed looks great on you. The tailor did wonderful work. Thanks for sharing this, it is all very helpful information. I have left the Americana workwear movement behind myself and discover the grace and simplicity of English menswear, less is more.

  10. Reply


    January 7, 2018

    My biggest lesson learned was a bespoke tweed sport coat that I had made a few years back. It came out fine (I realize now) but at the time I was convinced it was too long and had the tailor shorten it by an inch. Now it’s too short. This was a $1000+ mistake but what I took away was that I now know my ideal coat length.

  11. Reply

    John E.

    January 7, 2018

    Only regrets. Some purchases in the 70’s (the nadir of men’s wear) all now long gone. The error was departing from the classic highway. Otherwise my closet is full of suits, shoes, jackets, ties (neither too wide or too skinny), shirts etc. purchased over 40 years. I hate to tell my younger friends but those ultra short jackets and pants are not going to stand the test of time.

    • Reply


      January 7, 2018

      Ultra short jacket and pants? What are you referring to?

    • Reply


      January 13, 2018

      Amen. I see people in those short suits and they look like children that have out grown their clothes. What are they thinking?

  12. Reply

    Charles L.

    January 7, 2018

    This should be a list of 4 items, the first mistake being: ‘Buying anything on J. Crew at all (other than Alden shoes).’ I mean, not that I like online shopping, but eBay has made buying necessities such a cinch. I agree the color mistake is an easy one to miss until you get burnt the first time, and then you won’t ever make the mistake a second time. Perhaps an added item drawn from the last one might be: ‘Wearing anything for any amount of time if you’re not happy with it, and therefore are unable to return it.’

  13. Reply

    Peter F.

    January 7, 2018

    About your BB sport coat: Let me get this straight. If I understood you correctly, you have a regular tailor whose work you like. But you tried a new tailor, who did a lousy job on the coat. So you brought it to your regular tailor, who fixed it beyond anything you thought possible–and he didn’t charge you, doing the work, as you said, “on principle” (whatever that’s supposed to mean). Sounds to me as if this regular tailor of yours should be put up for sainthood. I certainly hope you wound up compensating him for his work, regardless of whether he charged you! You had the cojones to bring him someone else’s mistakes, admitting in the process that you ignored the long-standing relationship you have with him to try someone new, and then asked him to fix the mess. Not to pay him for his work would be to add insult to injury.

  14. Reply


    January 7, 2018

    Tweed, herringbone, Donegal plaid etc. are such great classic sport coats it just seems so not right to go the short, tight, slim/modern fit type tailoring. Leave it to your Royal Blue suit.

  15. Reply


    January 8, 2018

    I had long admired a particular tailor from Rome and had made this known to several friends. One day, one of them told me the tailor would be in our city for a fitting for a friend of his and he could arrange a fitting for me, too. How could I turn it down? I made the mistake of being so overly excited and so also too embarrassed to ask the price at the fitting (if you have to ask, you can’t afford… right?); the tailor never mentioned cost. Sticker shock followed when the invoice was sent some weeks later — it was double what I had guesstimated in my head. Whoops. It still remains one of my favorite garments, but there was definitely a lesson learned.

  16. Reply


    January 8, 2018

    I was just on my way to a cold New Years party and stopped by an outlet mall to get some dress gloves. Ended up looking at scarves at Brooks Brothers instead. I bought a Lambswool one for $80 or so because the nicer cashmere ones were $200. Then I go next door to Saks Off 5th and find cashmere scarves for $89 🙁 Well I had already taken the tag off the BB one and didn’t feel like swallowing my pride and going back to return it. (And also I liked the light color and pattern anyway) Is there a difference in quality in cashmere scarves to justify the difference in price?