When You’re New To Menswear… Where Do You Start?

“Where do I start?”

This is one of the first questions guys ask when they first get into menswear.

Unfortunately, it’s an incredibly difficult question to answer because the answer is different for everyone.

There are three things to keep in mind at the beginning of your menswear journey.

One is that in order to start, you’ll need to answer a handful of questions about yourself. These questions are hard to answer because they can’t be Googled like most other clothing-related questions.

Why am I doing this? More specifically, why do I feel the need to alter my current wardrobe?

What makes me feel good? And what does “good” mean to me?

What do I think looks cool?

What kind of man do I aspire to be and be seen as?

What kind of style speaks to me already? Is there any particular niche or genre that I already like? Why is that?

None of the answers to these questions can be found on StyleForum or AskAndyAboutClothes or Instagram or ChatGPT.

You’ll need to be comfortable with the fact that your reasons for beginning your menswear journey are yours and valid and cannot be validated by anyone else. That can feel a little scary.

For me, the reason I got into menswear was because I wanted to be seen as mature and capable. I wanted to be taken seriously. On some level I knew that life consisted of a ton of chaos and I wanted to exert control where I could. For me, “feeling good” meant looking like Cary Grant or Gregory Peck. All of these answers led me down a path that allowed me to discover things like tuxedos, tweed sport coats, and Aran sweaters.

Your answers might lead you down a somewhat different path. That’s ok.

Two is that knowing a good place for you, personally, to start, doesn’t mean the road won’t be long and winding. There’s no cheat code to make it so you’re starting on 3^rd base. Everyone’s starting place is different and the journey is roundabout. It’s not a straight line for anyone.

Think of starting out less like beginning at the startling line of a race track and more like being dropped into the middle of a pool. You’re treading water and doggie-paddling like many other people in the pool. Some other people are working on their backstroke. Others, their crawl. Some weirdos are even doing that flip-floppy, butterfly thing. Everyone’s just working on their own stroke. Sometimes they stick with the one stroke they like and get really good at that one thing. Other times, they’ll see what someone else is doing and start working on that, too. Eventually, you’ll get good at treading water and doggie-paddling and feel comfortable enough to take on a new stroke you saw someone else doing. Everyone is at different levels but everyone who is there just enjoys being in the pool. They’re not looking to race you or show off. They just like swimming.

That’s how all this works. Everyone is at different levels but they all just enjoy being in the pool.

Three is that there is no real “end”. You keep evolving and continuing to love things and find meaning and enjoyment in your clothes. So, enjoy the ride. If you’re focused on “finishing” or getting to the “end” then you’re going to get caught in this perpetual desire to get new stuff. You’re always going to be searching for the “missing link”, or the one piece that will finally complete your wardrobe.

But that “thing” doesn’t exist. Because the “end” doesn’t exist. Recently, I’ve realized that I am more or less “settled” in my style, meaning I no longer actively look for new stuff. I’ve come to the point where I find pleasure in the stuff I already have and don’t feel the need to continually add to my wardrobe. You might think that that’s the “end” for me, but it’s really not, it’s just a new phase of my own journey.

All of this can seem a bit confusing and bit overwhelming. But luckily, for men, there aren’t too many universally agreed-upon concepts for “well-dressed”. That means that what works for most men (and what has worked for most men for the past 100 or so years) will also work for you.

Most of the time, when men are getting into menswear, they are starting from a “jeans-and-t-shirt” place. While that might seem a long way away from “well-dressed”, it’s actually a really easy place to start because there are a few simple tweaks you can make to that combination which won’t feel like you’re putting on a pair of spats to run errands.

If you’re a jeans-and-t-shirt guy and are looking to up your style game a bit, just start slow. Instead of a t-shirt, wear a polo shirt or a collared, linen shirt with the sleeves rolled up. If it’s cold out, do an oxford shirt under a v-neck sweater. There’s no need to get rid of your jeans just yet. You can still wear your jeans with these outfits and look perfectly presentable (unless they’re soiled or ripped of course, but you already knew that).

Once you’ve got a couple nicer casual shirts to wear instead of your t-shirts, start to think about your footwear. I’m from the northeast so I always advocate for boat shoes in the summer but I realize that that preference might be a regional thing. If that’s the case then a pair of minimalistic sneakers in the summer is totally fine (although not my personal cup of tea). Just don’t wear sandals, as you really don’t want to be showing the world your toenails. For any other season, a brown, leather boot is your best bet. Chukkas, desert boots, Chelseas, and brogues are all fine choices for everyday boots. What you’ll find you like about a basic, brown boot is that you can wear it all the time with pretty much anything that isn’t a suit. And you won’t get the dreaded “Woah, why are you dressed up?” reactions you might get if you’re wearing something like a loafer.

Ok, at this point you’re wearing your sturdy boots and a nice, collared shirt. You’re going to have to have a pair of pants that’s not jeans. And that’s ok because there is a type of pant that is just as comfortable and just as hard-wearing!

Khakis! Or, to be more specific… chinos!

Chinos are an excellent replacement for jeans because you can wear them in all the same circumstances and you’ll look more put-together. They also come in pretty much any color you want so you don’t have to get the classic khaki color if you don’t want to. I find olive green to be a great choice.

There is no need to fret about wearing khakis and being seen as being “too dressed up” because khakis ARE casual pants! They were military uniforms for goodness’ sake and while I know that those connections are often lost on our modern minds, khakis are still pretty universally viewed as fairly casual, especially if you’re also wearing a polo shirt and boots.

Your next step is tucking in your shirt! Ok, that might sound like a bridge too far, but once you have a couple nice shirts, it’s the logical next step. Sure, a polo shirt can be left untucked, as can an oxford shirt in some situations, but most of the time you’re going to need to tuck those long shirt hems into your pants. This move will be a very clear indication that you are “getting dressed up” so be prepared for that.

But to me, that’s how a mature man dresses. Think about your grandfather. I bet he tucked in his shirt.

Once you have the “decent shirt, pants, shoes” thing down, your next step after that is to think about something like a sport coat.

But when you get to this point… pause! Take a breath. Get comfortable with your new look. The pieces you’ve been experimenting with so far are relatively cheap and easy to get in a variety of sizes. When you start getting into actual tailoring (sport coats, blazers, suits), you’re going to need to have a certain baseline of knowledge of how things are “supposed” to fit so that you can make informed purchases.

This is where some research will do you good. You should have a basic understanding of how a tailored jacket should fit before you walk into a shop prepared to drop a few hundred dollars. If you still think a sport coat is going to feel like your favorite hoodie from college, you’re not quite ready to make the move into tailoring quite yet.

For me, I gained that knowledge from Peter Marshall’s “Black Tie Guide”. As I explained in my own guide to black tie, reading Marshall’s work provided me with a strong base for understanding not only formal and semi-formal etiquette, but the tenets of menswear on the whole.

Personally, my “menswear starting point” was obsessively reading about tuxedos in preparation for my wedding. That’s what I mean about how everyone’s starting point is different.

One of the most important things to keep in mind, though, is that the clothes don’t matter in the grand scheme of things. The clothes are not the point. The clothes are not the endgame. The clothes merely accompany us on the adventures of life.

A jacket is just a jacket until you wear it out to dinner with your wife. A hat is just a hat until you wear it on that rainy vacation. A watch is just a watch until you wear it on that high-stakes interview.

No matter where you’re starting from, remember that they stuff you do is more important than the stuff you wear. Living a life full of adventure and putting your clothes through their paces will make you much more stylish than the guy who spends all his time scouring the internet and fastidiously trying to put together the perfect outfit. Paradoxically, the less you focus on the actual clothes the more enjoyment you’ll get from them.

The fact that you’re trying to improve your style is a wonderful thing. It shows that you’re dedicated to personal growth. And you WILL get to where you want to be with your style. It could happen quickly, or it could take many years. Honestly, it probably will take many years.

But remember to enjoy the ride. If you’re not enjoying it, you’re doing it wrong.