The Incredible Benefits Of “Boring” Style

What’s wrong with having boring style?

I am often accused of having “boring style.” Granted, this brand of criticism occurs most frequently by way of very thoughtful and considered one or two word comments when a video of mine has caught the wave on YouTube Shorts or TikTok, but I think it’s a topic worth investigating.

I think what people actually mean when the tell me I have “boring style” is that, basically, my style is simple. And you know what? If that’s the translation, they’re right! My style is very simple. Suit and tie. Sport coat and trousers. Loafers or lace ups. A simple pocket square. That’s me. And if that’s “boring,” well, I’m totally fine with that because there are some incredible benefits to dressing that way.

I’ll identify each of those advantages below and provide a “boring style” starter wardrobe, but first I’d like to talk about the journey I took to find my current style and how I became comfortable and confident in that.

My Journey To “Boring” Style

When I was a kid . . . just kidding, it’s not going to be that in-depth. We’ll fast forward to the time period when I finally decided to get serious about cultivating my personal style and building a proper wardrobe — about 13 years ago.

When I finally made the commitment to “get into style” some interesting things started to happen. When I got my very first taste of what dressing well can do for you, I officially reached the point of no return. Suddenly people seemed to take me more seriously, I got better service, and most importantly, I was imbued with a newfound confidence in myself. Now, I also got my fair share teasing and ridicule from some of my work colleagues, but that honestly said more about them and their insecurities than it did about me.

Then, I became guilty of making the worst men’s style mistake.

Trying too hard and being possessed by the desire to show people you are “into style” is an obligatory misstep for those of us who love classic menswear. I’ve not met one person who hasn’t shared a similar story of regret detailing their cringe-worthy sartorial experiments.

Interestingly, although my gateway to and earliest icons of men’s style were pretty standard fare — James Bond (Connery vintage), Cary Grant, and later Don Draper — I was searching for something different than you’d see those guys wearing. It wasn’t that I thought they were boring, but I wanted to distinguish myself in some way.

Shop This Look

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Classic Navy Blue Blazer

$495

Baby Blue Poplin Dress Shirt

$175

Silk Rep Sidewheeler Striped Tie

Brooks Brothers

Medium Grey Wool Pants

$245

Full Strap Loafer in Color 8 Shell

Alden

White Poplin Pocket Square

$39

This was at the height of #menswear and I, like many others at the time, “discovered” and became mildly obsessed with classic Italian style and all of its trappings. Bold! Colorful! Bracelets! Double monks! Oh, my! Imagine all the possibilities. Unfortunately, I did. The funny thing is that even when I was experimenting with all of this stuff, as confident as I may have looked, something inside never felt quite right.

In addition to my Italian obsession, I also became pretty fascinated by Thom Browne. His now-defunct Black Fleece line for Brooks Brothers was (and still is) pretty amazing. I owned a few pieces and loved wearing them. Yet unlike my Italian style experiments, I did feel very comfortable wearing those pieces. They were bold and, honestly, wild but since they were rooted in classic menswear they felt more like “me.” Eventually, though, I outgrew those pieces — literally and figuratively, a retired bicycle-racer’s metabolism doesn’t keep cranking forever . . . — and I began to enter a new chapter in my quest.

My style journey is inextricably linked to the rise of menswear influencers and the development of an entirely new paradigm. Myself, along with a handful of others, were at the tip of the spear, defining whatever this new thing was. It was fun, but also difficult and exhausting mentally.

The constant need for more content and to “feed the beast” coupled with competition in an ever-evolving landscape was not healthy. There was an expectation that you had to keep posting something new and different. Let me tell you, it felt like being trapped in a maze running around with a bunch of rats. You’re performing and you create this imaginary sense of obligation. I see people going through it now and I feel sorry for them. It’s unsustainable and bad for your mental health. It’s also not reality and I came to hate representing the idea to people that you constantly had to have something new, like every single day.

That’s when I started to long for something simpler. I guess that arrival came from a place of “been there, done that,” but I was no longer turned on by the things that once got me going. Going through all of that got me to the point where I knew what I liked and what I was most comfortable wearing.

That was, of course, classic menswear with a modern sensibility. I feel good wearing simple outfits that are not over-engineered. I’m confident in them. I think I look good in them too, if I can say that. Unlike my Italian era, dressing this way just feels “right.” And I’m totally down for that being my thing. I will throw a curveball every now and then, but for the most part, I’m keeping it classic. Haters gonna hate.

Now that I’ve taken you through a short tour of how I got from Point A to Point B, let’s take a look at three amazing advantages of having “boring” style.

Advantages Of “Boring” Style

• Always in style. The first is that you will always look good. A “boring style” wardrobe consists of classics — those timeless menswear pieces that always have been and always will be in style.
• Less thought involved. Second, a simple and classic wardrobe makes it really easy to get dressed. Like, really easy. Everything is versatile, it can pretty much all be paired together, which means it doesn’t require much thought. Think about what you could do with all that extra brain space.
• Set and forget. And third, when you curate a classic menswear wardrobe, it’s pretty much definitive. So if you buy once and buy well, you’re set for a long time, which makes a lot of financial sense.

10 “Boring” Style Wardrobe Essentials

What do you need to build a “boring” style wardrobe? Turns out not much. And here are 10 pieces to get you on your way!

Navy Blue Hopsack Suit

Navy Blue Hopsack Suit

$695

A true workhorse suit, as exemplified by its best-seller status in the HSS Shop, and one that I always like to recommend as a first suit or only suit for two reasons. First, it’s incredibly versatile. Simple to style with a wide range of colors and very easy to dress up or down. Second, with a hopsack suit, you don’t just have a suit. Because of the fabric, you’ve also got an incredibly versatile sport coat and pair of trousers as well.

Patterned Sport Coat

Gray and Brown Houndstooth Sport Coat

$995

The easiest way to exponentially expand your options is to supplement your wardrobe with a patterned sport coat. A classic houndstooth pattern in gray and brown is super versatile, perfect for business casual dress codes, can be worn with jeans, and even smartened up with a tie.

White Dress Shirt

White Poplin Dress Shirt

$175

I mean, what is there to say about a white poplin dress shirt? You’ve got to have one — but, to be honest, owning two or three is probably a really good move. Always looks good with a tie and can be worn without for a more casual look.

Blue Dress Shirt

Baby Blue Poplin Dress Shirt

$175

Just like your white poplin dress shirt, but perhaps a touch less formal. Wear it dressed up with a suit and tie or more casually with a pair of khaki cotton trousers (see below).

Gray Trousers

Medium Grey Wool Pants

$245

If you’ve taken my advice and gone with a navy blue hopsack suit, adding a pair of gray wool odd trousers is a logical addition. They’re never a bad choice and are a must-have if you’re a fan of the classic “menswear uniform.”

Khaki Cotton Trousers

Khaki Cotton Pants

$195

A staple of business casual, smart casual, casual, and preppy styles, you will get a ton of mileage out of a pair of khaki cotton trousers. Take them as styled here with a cuff and a crease — Dr. Dre approves — or go with a plain bottom and no crease for a more casual feel.

Lace-Ups

Dean Oxford Dress Shoes in Dark Brown

Beckett Simonon

For dressier looks in this “Boring Style” capsule wardrobe, a good pair of leather lace-ups are a must. While you may be inclined to choose a black pair, you’ll get a lot more mileage out of a dark brown pair with the pieces featured here.

Loafers

Cohen Loafers in Bordeaux

Beckett Simonon

I love how easily it is to knock down the formality of a look with a pair of loafers. Although they can certainly look “dressy,” they affect an air of stylish, casual nonchalance. In a deep burgundy, oxblood, or Alden’s famous Color 8, they’ll add an incredible amount of depth to your wardrobe.

Classic Necktie

Navy Blue Pin Dot Silk Necktie

$165

Because we’ve got so many solids in this capsule wardrobe, I’ve decided to pick a necktie with a classic and not overbearing pattern. A simple pin dot will provide just the right amount of visual interest and always looks good.

White Pocket Square

White Poplin Pocket Square

$39

You could spend a lot of time, energy, brainpower, and money searching for the perfect “cool” pocket square to complete your outfits. Believe me. Been there, done that. You know what always looks good though? That’s right, a simple white pocket square. It’s the one I reach for nine times out of 10 on a daily basis.

The Bottom Line

More than anything, what I’d like you to take away from this post is that you don’t have to go overboard to look and feel your best. I believe that simplicity in style is a virtue. It’s also a way to ensure you are always in style, a path to making the act of putting an outfit together extremely easy, and a way to curate a wardrobe that will stand the test of time. I do think experimentation is a very good thing — I wouldn’t have arrived at this point without doing it myself — but hopefully this will help inform your decisions wherever you are on your own style journey.

Thanks, as always, for reading.