Five Ways To Improve Your Style

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Ratty t-shirt. Sweatpants. White socks. Baseball cap. Another ratty t-shirt. Does this sound familiar? I pray to the Lord that it doesn’t… but if it does, I am here to help. I’m not asking you to make a radical switch, but I present five simple ways to improve your style. After all, I’ve never heard a woman tell me, “Wow Jayson, I wish you’d wear more Ed Hardy.” Boom.

[Your girlfriend/fiance/future-wife/woman-of-your-dreams will thank you. Trust me.]

1. Throw out every white undershirt you own.

Trust me here.

Ever heard of bacon neck? Hanes has… and they even produced a commercial about the former-quality of their useless undershirts. This is the least of your worries.

The white undershirt is unnecessary. It has no place. It’s the male version of seeing a woman’s bra through her blouse… except they don’t think it’s sexy. It screams, “I am 11 and my mother has dressed me on this day!”

Drop them. They can’t be worn under any type of men’s shirting, and they’re too ratty to be worn alone. Do you remember how, if used long enough, the underarm area gets all wrinkly and yellow? People see that.

There’s no easier way to get written off as someone who doesn’t know what they’re doing, than to wear a white undershirt. Pick a graphic tee or wear a men’s shirt. Not both.

2. Buy a watch.

Before you throw up your arms… I’m not asking you to procure a $25,000 Breitling. This is attainable.

Let me clarify too:

This is not “a watch.” In fact, maybe it’s a watch in some circles, but really you’re looking for a timepiece. A good place to start is a Timex, like this Military Watch from J.Crew. It has a black face, with changeable straps, and is extremely durable. The reason I love this watch is because of its’ versatility, though. I own seven different watchbands, in varying colors that are suited for most every occasion: black, black/silver, tan, navy, and so on.

You can find vintage Timex pieces on eBay or you can even go the cheaper route and shop Target for some easily customizable Timex-brand watches. These watches also use the same watchbands from J.Crew.

A canvas watchband with a buckle closure is very easy to clean and maintain. It is an excellent transition into the timepiece arena, and will set you up nicely for something more expensive, like this Citizen Eco Drive.

3. Purchase a pair of boat shoes.

This is your intermediary step to men’s shoes. The classic boat shoe is, well, classic. It can be worn sockless. With pants. Without pants.

The Sebago Spinnaker boat shoe.

The boat shoe is great because it doesn’t require the investment of a small village to purchase some loafers from Ralph Lauren or Del Toro. My Sperry Topsiders have lasted longer than any shoe I’ve ever had, so it’s a testament to the durability of an all-leather shoe. Furthermore, you can escape the stage of wearing just sneakers and flip flops.

4. Understand what a button-down is, and then buy a few.

It’s time to set the record straight: a button-down is not any men’s shirt. A button down is a type of collar.

One time, many years ago, I was publicly reproved by an older man inside Nordstrom’s. I said I was looking for a few “button downs.” He took me to the button down collars, and when I said I wanted something different, he told me, “This is what you said you wanted!”

I learned something that day. There is a difference.

Call it a shirt. A t-shirt can be a ‘tee’ or a t-shirt.

On that note, pick up a few button downs. They are less dressy than a straight collar and more durable (because the collar is essentially pinned to the neck, it can’t lose its’ shape). Here are two great choices from J.Crew: The mini-ginghamThe sun-faded solid oxford.

5. Commit to buy a new belt every year.

Speaking collectively for men as a whole: we need more belts. As I grew up, I probably had two belts (black and brown). I’ve spent the past five years trying to compensate, and even so, I might have ten belts total (and of those ten, I might wear three). Belts aren’t a huge monetary investment, but a good belt will last forever.

The reasoning for buying a new belt once a year is two-fold. First, it’s a great barometer for your overall level of fitness. If you need to wear a 34 instead of a 32, you might have incentive to avoid jumping up a size. Also, it let’s you experiment. When you’re buying a belt once in forever, you’re likely replacing that standard-issue black or brown belt.

Having the ability to branch out into other colors or patterns gives you the opportunity to be different. Different is good.

Also of note: Needlepoint belts. They’re expensive, but awesome. There’s no better way to say I love the Charles River, Kiawah Island golfingor lacrosse, than these belts:

The Iroquois Lacrosse Needlepoint Belt from Tucker Blair - $65

More from Tucker Blair here. And also Smathers & Branson.


[Photo: Aditya Rakhman (cover)]

I am the founder of the Quarterlife movement, curating content by day and running a digital agency by night. I am on this planet to call out vision in others. I love Detroit sports and CrossFit. Connect below via social media or by email: jayson (at)