10 Wardrobe Items I Regret Buying (Menswear Fails)

Style is a journey and, sometimes, even the best of journeys have a few wrong turns. Stick around to find out what I’ve bought throughout the years that maybe what I shouldn’t have. One of the biggest parts of being a gentleman is owning your mistakes. We’re all human, and no human is perfect and today, I’ll walk you through some of my biggest style purchase mistakes. 

If you’ve seen what other members of the Gentleman’s Gazette team have regretted buying in the past, you’ll have a pretty good idea of how this list is going to go.

1. Too Many Double-Breasted Jackets and Suits

Let’s get started with my first item. I got these when I first started getting into a custom suit shop. I was working there part-time. These cost me about 300 bucks a pop, depending on if I was buying a suit or just a jacket.

What I really like about them at first is that I really admire double-breasted jackets. I admired double-breasted jackets so much because they were so unique and they weren’t easy to find off-the-rack, so I went really deep.

I started realizing that this was a little regrettable when the versatility of a double-breasted jacket just wasn’t there. I love to mix-and-match my formalities, but sometimes, these double breasted jackets just look off when I am wearing them with jeans.

So, I really had to steer the other direction when it came to the closure of my jackets, so I went to single-breasted jackets and these were much better when I wanted to wear them with jeans, and I wanted to really mix-and-match my formalities.

My advice to you would be to start with single-breasted jackets first or suits when commencing your sartorial journey, especially when you’re buying an investment piece.

2. Bold-Patterned Items

So, right around 2014, this was a huge hit. These probably cost me a total of maybe 100 plus. I like that they made a statement and gave a pop of color or fun to my outfits. I started realizing that this was a regrettable purchase when these items were not very versatile, and the trend started dying out.

I have not replaced these items. I just simply got rid of them. Steering more towards classic solid colors and, if I want something with a pop, I look at getting something with more texture than pattern.

As much as we like having bold-patterned pieces, sometimes it’s better to just sprinkle in something bold here and there.

3. Wacky Socks

These were also a big hit around 2014-2015, and they were very inexpensive. So, I bought a few of them. As you can tell, I really like to express myself through my clothing. But, wacky socks are really “in,” and I wanted to give my look something different. Again, to my dismay, this trend didn’t stick around too long.

It seems like they’re only used for company Christmas parties. Again, I went the complete opposite way and bought solid-colored socks.

I recommend sticking with basic, solid colors. If I want a pattern, I try to keep the design minimal.

4. Camouflage Field Jacket

I bought this just recently, maybe about two years ago; cost me about $40. I kept seeing others on Instagram putting field jackets over their suits, and I thought, “Hey, it was an awesome and creative way to incorporate my military background into a look.”

My advice is you have to try it in order to know that it’s not for you.

5. Hats

I’ve tried to buy hats throughout the years, and I spent quite a bit of money on them. I like the way the hats look on others, so I thought, why not give it a try?

I was really inspired by the pork pie hat from the movie Takers, where Hayden Christensen’s character, AJ, wears one and looks so cool. I went out and bought one and tried it on. It didn’t look good on me. I also tried wearing a few fedoras; those also did not work out. So, since then, I have decided to just stick to ball caps.

There are a ton of different hat styles. Don’t be discouraged if it takes you a while to find the right one for you. Plus, we’ve got a guide on how to wear hats confidently.

6. Baggy Clothes

This was the thing back in 2006. I was in middle school, high school, and “Lean Wit It, Rock Wit It” was a huge thing. Again, I fell into the trend. I was in high school and everyone and their mom literally were into this style. I started realizing that this style was not for me because it just made me look shorter than ever.

Since high school, as you can tell, my style has changed to more tailored, timeless pieces. You live and you learn. It is beneficial to see what works for you and you only. Not what others are into. It’ll save you hundreds, if not,n thousands.

7. Buckle Graphic Tees

This was a trend back in 2010. These T-shirts were about $50, and I really liked them just because they were in trend. They had the whole Tapout logo or maybe they had some bejeweled parts to the T-shirt. So, I was very intrigued.

This trend died out faster than Vanilla Ice’s rap career. Since then, I’ve decided to move to more classic tees. Just plain whites, grays; things that are very versatile that I’m able to wear with just about anything. These tees are somewhat loud and, sometimes, you don’t want to have that kind of attention. Sometimes, less is more. So, I would stick to the basics.

8. Big Fashion Watches

A few years ago, brands like MVMT, Daniel Wellington, and other watch brands were becoming very popular. Although the watches were affordable, they were very badly made, and their batteries didn’t last very long. The watch faces were so big that they looked abnormally off on my small wrists.

I’ve learned to save up and buy watches that are of higher quality and stand the test of time; they also look better on my small wrists. A timeless watch will definitely cost you more, but it’s worth it. 

9. Creative Tie Clips

This was a popular item in 2017. They were very inexpensive, they were about $40-$50, and what I liked about them was that they gave me a creative outlet in my style, and they came in so many different designs.

Again, this was just a fad. Not too many times could you show up to a meeting with the whale tie clip on. Tie bars are a great accessory, but it’s better to keep them on the classic end.

10. My Green Linen Suit

I bought this back in 2021, and it cost me about $700, and I absolutely love the color. I envisioned the suit, and I thought it would look spectacular. It’s not the color of the suit that was a problem; it was how I designed it.

I wanted to incorporate a pleated shoulder on this jacket because it’s a little bit more casual; however, with this style of jacket, which was unconstructed, it just did not look good, and I felt that the way that the suit draped also didn’t flatter anything. The fit of the jacket was also off, which made it even worse. I tried to salvage the pants, but I did a drawstring waistband that wasn’t in the style that I wanted, so I couldn’t save those either.

Needless to say, this design blew up in my face. I do plan on remaking this suit and doing it the right way, so stay tuned.

My advice to you: In the world of custom, where the possibilities are endless, sometimes less is more.

What do you think about my list? What regrettable items are in your wardrobe? Share with us in the comments below.

Outfit Rundown

Today’s outfit is regret-free, comprising a burgundy suit in the fabric of Stylbiella, and I really like the color of it. I designed it with a ticket pocket, and I have peak lapels. I also have a pocket square from Fort Belvedere. I have a white shirt on from my brand, and I have a pair of burgundy penny loafers from Beckett Simonon. My fragrance today is the Marzocco from the Roberto Ugolini Collection. You can find this collection, as well as other classic menswear accessories, in the Ford Belvedere Shop.