10 Wardrobe Items I Regret Buying: Poor Menswear Choices (and Their Stories)

All of us have had our fair share of buyer’s remorse! With that in mind, we thought it would be helpful to share my personal experience, by laying out ten things in my wardrobe that were regrettable purchases, why I bought them, and what I’ve learned since then.

If you haven’t seen Raphael’s video on 20 things he regrets buying, I’d recommend taking a look. You’ll probably learn some things not only about men’s style but about money management, as well. Today, we’ll cover a similar ground for items I’ve purchased (whether that be individual garments or collections of things), with one key difference from Raphael’s video: I don’t actually regret buying all of them. You’ll understand what I mean by this later, so let’s get the ball rolling.
Things I Truly Regret Buying 1. Antiperspirant
The first thing item on my list is clinical strength antiperspirant (and antiperspirant in general). As I’ve mentioned elsewhere on our Youtube channel, I have a condition called Hyperhidrosis, which is marked by excessive perspiration. Sparing all of the details, what’s important here is that over the years, I’ve tried numerous products to try to minimize perspiration across my body. When it comes to my underarms, I used a clinical-strength antiperspirant for many years, but because my perspiration was so persistent, all I would end up with was an unpleasant sludge under my arms after usually just a few hours.

Antiperspirants

Also because aluminum is a key ingredient in many antiperspirants (serving to block the pores), it can corrode over time–and this, more than bacteria or the sweat itself, is the thing that chiefly causes underarm stains on shirts. With all the aluminum that was in that antiperspirant, there was even a time or two that I set off an airport metal detector–I’m not kidding! About two years ago, I decided that if these antiperspirants weren’t doing a good job of stopping my sweating, and if they were causing these inconveniences besides, I might as well stop fighting the root cause.

Clinical Antiperspirant

Since then I’ve switched to non-antiperspirant deodorant, and while I do still sweat quite a bit (and may seek other medical solutions in the future for it), I have found that not using an antiperspirant to fight my underarm sweating has left me feeling better overall.
2. Two-in-One Shampoo & Conditioner
As we’ve previously mentioned in our video on 15 healthy hair tips, there are a number of reasons not to buy combination shampoo-conditioners. First off, shampoo is something that can actually do more harm than good to your hair if used improperly. Cheap shampoo, though it is economical, is often full of ingredients that are collectively known as sulfates. While these detergents can help to make the product sudsy, they also deprive your hair of its natural oils, leaving it looking dry and brittle. To avoid these effects, you can look for a low-sulfate or sulfate-free shampoo, which cleans without removing the oil completely.

2-in-1 Shampoo and Conditioner

Second, and perhaps more importantly, you actually don’t need to use shampoo every time you shower. Constant shampooing, even with sulfate-free products, can strip your scalp of natural oils and will definitely dry out your hair, even if it’s already somewhat dry, to begin with. Therefore, most barbers and stylists will recommend that while you should rinse your hair every time you shower, you should only use shampoo one to two times per week. What you should use more often–and even daily–is conditioner, which helps to protect and moisturize your hair.

Sulfate-free shampoo

All that to say: these combinations or two-in-one products are essentially making each of their components less effective on both fronts. Also, it should go without saying, but for any of those three-in-one combination products which also include body wash: stay away. I used a two-in-one product for years, but since switching to separate shampoo and conditioner about a year ago, I’ve noticed that my hair feels noticeably healthier. I only shampoo about once or twice a week, usually following whenever I’ve used a hair product. I haven’t written off liquid products entirely and switched to bar soap as Raphael has, but it may be something to consider in the future.
3. Medium Gray Suit
I purchased the gray suit pictured below seven years ago at the age of 18, and it was my first true suit. The trousers came unfinished, so having to go to an alterations tailor to get them hemmed made me feel like I was getting the suit to fit just right. Little did I know at the time, though, that there are actually many more facets to getting a suit to fit you well. The construction and materials of this suit are also quite cheap, which made for a low price point that was attractive to a cash-strapped student like me. But as we’ve said many times before, cheap materials are secondary to a proper fit. Of course, I readily admit that this suit is far from properly fitting on me!

Preston’s first suit: definitely not a proper fit!

The jacket is much too big in the torso for one thing, so it looks like I’m practically swimming in fabric. The trouser legs are also too wide for my build, but because the fabric is light, there isn’t any attractive drape to them, just ugly wrinkling. I could go on, but suffice to say that this suit definitely doesn’t meet our fit criteria. I could probably try to have it tailored further to get it to fit better, but I think a better choice would be just to find a suit that fits better from the outset and is of a higher quality. Where did I get this suit, you ask? The answer is the now ever-present force in so many of our lives: Amazon.com–and that leads to my next pick…
5. Most Garments from Amazon
Several of the other garments I’ve bought or tried to buy from Amazon haven’t turned out well for me, either. From a sport coat that was too boxy on me and of low quality, to trousers that were far too baggy (sensing a pattern here?), to cheap ties, I’ve realized especially since joining the Gentleman’s Gazette that buying clothing sight unseen from a cheap, mass-market retailer instead of a dedicated menswear outlet means that you do get what you pay for, which is usually disappointing results.

Ties from Amazon; most are cheap and made from low-quality materials
5. My Shiny Synthetic Ties
The next items on my list of regrettable purchases are the overly shiny, satin-silk or synthetic ties in my wardrobe. Some of these were purchased from Amazon, and others were purchased in-person from stores, but the common denominator here is that their blindingly shiny finish and often bright, loud colors make them look like cheap, low-quality ties almost immediately.

An example of a synthetic tie

They were at least tolerable for a young man just getting into menswear, but since learning about the hallmarks of a quality tie, especially like those from Fort Belvedere, these shiny ties don’t see much use for me anymore; outside perhaps of a Halloween costume.

A selection of high-quality madder silk bow ties from Fort Belvedere
6. Low-Quality Dress Shoes
Similarly, cheap and low-quality dress shoes are my next item here. Before joining the Gentleman’s Gazette, I viewed dress shoes in a way that’s similar to many men out there–which is to say that in today’s fast-fashion society, shoes should be purchased for a reasonable price of around $100 or so, worn until the materials wear out, and then thrown away and replaced. Some examples would include a cheap pair of loafers and the derby shoes pictured below.

Low-Quality Derby Shoes

The truth about men’s dress shoes, though, is that if you’re willing to spend a bit more at the outset, say something in the $200-$400 range, you’re going to be able to find shoes that are made of higher quality materials and with better construction. Take, for example, the Park Avenue from Allen Edmonds. For a sticker price of $395 (but often on sale for less), you’ll be getting a shoe made from quality leather in both the upper and the sole, rather than a cheap shoe with a cheap leather upper and a sole made from rubber, plastic, or particleboard.

The all-leather sole of an Allen Edmonds Park Avenue dress shoe

Also, we’ll note here that shoes with a Goodyear welt or a Blake stitch can be re-soled by a cobbler. So, if you maintain the upper properly, they can be worn for years, if not decades. Meanwhile, these cheap shoes had their heel blocks worn down in around a year’s time, and because the soles are just glued on rather than stitched, they can’t reasonably be repaired. In addition, the cheap leather uppers are showing discoloration in an unattractive way, and because the shoes are slightly too big on me to begin with, they’re also wrinkling unattractively. 
Things I Could Regret But Don’t
The next four picks that round out my list today are things that could be considered regrettable, but for one reason or another, I’m still glad that I bought them.
1. Charles Tyrwhitt Shirt Collection
First up is my fairly extensive collection of Charles Tyrwhitt shirts. Why would these be considered regrettable? Well, in one word, the answer is fit. All of these shirts are much too big on me in both the torso and the arms. Because they were my first foray into online made-to-measure, I selected “slim fit”–not knowing that for someone as light and thin as I am, this would still be much too big on my frame. Also, I started collecting these shirts before joining the Gentleman’s Gazette, so I didn’t have a complete picture of how a dress shirt should actually fit.

A Charles Tyrwhitt shirt in pink, paired with a tie, collar clip, boutonniere, and pocket square from Fort Belvedere

Why don’t I regret buying them? As I said, they were my first experience with made-to-measure, and I appreciated going through the process and having something that was made for me, even if they aren’t truly bespoke. Furthermore, I now most often wear them underneath jackets or sweaters, so their too-large fit is somewhat obscured, and they still work for me for the time being, as I look toward the future to upgrade my shirt wardrobe. And as I’ve mentioned before, I still get plenty of compliments on them, as well!

Oversized dress shirt

Finally, learning that something doesn’t fit well on you is still learning. Style should be an ever-evolving journey, and these shirts have played an important part in mine. Also, the difference between these and something like my gray suit is that while I can find ways to still make the shirts look reasonably good, the fit of this suit is immediately apparent, so it’s really a no-go for me at this point in time.
2. My Black “Suit”
I mentioned in the first half of my list that my gray suit was the first true suit that I owned. This is because the first “suit” that I had wasn’t really a suit at all! Back in high school, I participated in forensics, which is to say, speech and debate teams. At least at that time, the standard uniform for men was a black suit. Being young, inexperienced in the ways of menswear, and on a budget, I simply picked up a black jacket from a department store and paired it with a pair of black trousers that I’d already had for years.

Fortunately, the dyes and weaves of the two garments were similar enough that to the casual observer, they actually did appear to match. But as we’ve discussed numerous other times, a suit is made from a jacket and trousers (as well as an optional waistcoat) that are all cut from the same fabric. As with the gray suit, the black jacket was much too baggy on me.

Preston Wearing His Black “Suit” (Photo: Sydney Gerten Photography)

Why don’t I regret my black “suit” ensemble, then? The answer is because it made me feel confident and in control, as a suit ideally should. It wasn’t strictly correct by the guidelines of menswear, but it was for me a “suit of armor” that helped me feel more comfortable giving speeches in front of people (something with which I had struggled earlier in childhood). In fact, if I hadn’t joined these speech and debate teams in high school, I probably wouldn’t have been confident enough to eventually find my way to on-camera speaking, or joining the Gentleman’s Gazette. I’m not saying that this black “suit” was directly responsible for this, but it did probably play a small part.
3. Black Wool-Felt Fedora
Around the same time as the purchase of my black “suit,” I was a teenager just getting into the world of menswear. I really didn’t know much about fit yet, but I knew that I wanted a hat to go with my suit. As such, I found a black wool-felt fedora online. It wasn’t a cheap trilby bought from Target (which were quite popular around 2011 or so), but in fact, a genuine fedora purchased from a hatter. While it was pretty soft in construction, black wasn’t a flattering or versatile color for me, and the brim was too wide for my face, this hat did still give me confidence. I wore it often with that black “suit” in high school and even with non-matching outerwear for my first few years of college.

Preston’s Old Fedora Hat

Once I started looking around for vintage fedoras on eBay and in secondhand stores, however, I began building up my current collection, and this hat stayed on the rack. I still haven’t gotten rid of the old hat yet, because it holds a special place in my wardrobe. And who knows–maybe for ultra-casual outfits or doing things outdoors where I’d still like to be wearing a traditional hat, and black works in my wardrobe, it could still have a place.
4. Pre-Tied Bow Tie
As regular readers are no doubt aware, we here at the Gentleman’s Gazette recommend that a man learn to tie his own bow tie whenever possible. A pre-tied bow tie is cold and sterile in its perfection, and it immediately gives off a juvenile, unprofessional look. But in fairness, I first purchased a pre-tied bow tie at the age of 15, when I was still a juvenile and a non-professional! I needed it for a makeshift tuxedo of sorts, so I wore it along with a borrowed black jacket and those trusty black trousers, to serve as master of ceremonies for a school concert in the spring of 2009.

Pre-tied bowties are so symmetrical as to look sterile

My lack of regret for purchasing this bow tie comes from the fact that it did make me feel confident in front of a crowd, honing my skills as a presenter for really the first time, even before later joining the speech team.
Conclusion – What Lessons Have I Learned?
The ten things on my list today are six that I truly regret buying, and four that could be regrettable, but have played an important part in my own style journey.

Preston in his black “suit” and an inexpensive bow tie (Photo: Sydney Gerten Photography)

So, while abiding by the traditional guidelines of classic menswear is a surefire way to get yourself to a stylish wardrobe, don’t be afraid of experimenting when you’re first starting out in that world, no matter how old you may be. We can all learn through trial and error, with the ultimate goal of becoming more stylish.
Do you have any regrettable items in your wardrobe, and if so, have they taught you any style lessons? Share with us in the comments! #Ties #Wardrobe #SyntheticTies #ShirtCollection #FedoraHat