men's basics

Men’s Style: 11 Badass Basics Every Man Should Own in 2019

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StyleOtter | Men's Style

Let’s get real about men’s style. 

Have you ever spent money on sneakers that look stellar, only to realize that they don’t really go with the rest of your style? 

Maybe you’re over defaulting to wearing the same shirts from high school (we’re raising our paws) and you know that it’s time for a wardrobe do-over. 

Unless, maybe, you have your wardrobe built – even though you may also have about 50% of clothes in there that you wear, and 50% that you don’t. Ouch.

OK, well, don’t get intimidated.

What about the go-to items that you could toss on and look great? The items that should be getting repeated wear in your closet, because they just look so damn good? 

StyleOtter wants to equip you with the top timeless essentials that we believe every man should own. We’re talking basics. We’re talking quick. We’re talking easy.  

Trust us, we’ve been there. And we’ve got your back.  Let’s get started.

a great pair of denim

blue denim

You know the pair.

The kind that makes you look and feel so good that you can’t fathom owning another pair of jeans that would be this heaven-sent. 

Oh, wait.

Maybe you don’t know the feeling. Well, let us enlighten you.  

Quality denim is supposed to be comfy, slightly stretchy, and breathable.

The fit can be across the board, but what we love about a great pair of denim is that it’s dependable.  

We think investing in a great pair of denim jeans is one of the best ways to kick start your wardrobe and your personal style.  

Here are a few different pairs of denim we love:

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When looking for denim, a few things to keep in mind: 

  • Always wash your jeans after you buy them. You don’t know who’s tried them on before you, and if they’re dyed, the dye might rub off on clothes
  • Invest in jeans that will last longer, and learn how to take care of them better (see our post: How to Make Jeans Last)
  • Since we’re suggesting timeless basics, consider investing more money into items that aren’t as trendy, such as ripped jeans. We believe you’ll end up getting more mileage

a killer grab-and-go bag

men's bag

We dream of the bag that is truly multi-faceted, long-lasting, yet looks pristine under most weather conditions.  

But that bag could end up taking a long time to find.

And as you know, sometimes it takes weeks and months of back and forth before pulling the trigger. 

Luckily, we’ve found a few different options that could cover off on your different needs – daytime errands, going to the office/traveling, or grabbing the kids from daycare. 

Here are a few different grab-and-go bags we love:

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A few things to keep in mind as you consider investing in a new bag:

  • Know where you go, and the type of climate you live in. While we’d like to think the options we selected are up to snuff, you never know how the weather might have an impact on the wear of your bag
  • Keep in mind this bag might be going everywhere with you – therefore it’s best to know which colors you have in your wardrobe and how this bag might complement them. For example, if you’re always wearing black, consider investing in a different color to help your clothes pop

a versatile pair of shoes

men's shoes

Shoes are one of those wardrobe items that can instantly take your outfit to the next level.  

However, styling shoes with the right outfit require a good eye.  

We’re partial to sneakers and dressier shoes that are easy to toss on with jeans, a sweater, and a backpack.

They’re also great for transitioning from day to night, and even date night.  

We’ve found a few different options that fit the shoe bill:

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And a few things to keep in mind as you’re browsing your shoe selection:

  • Walk a mile in those shoes – it sounds like we’re kidding, but we’re not. Especially if you’re investing in a more expensive pair, make sure that you give the shoes a good test run. This is why we love a retailer like Nordstrom, since their customer service and return policy is top notch!
  • Keep material in mind. If you’re going to be outside at all, it’s best to buy a protectant for materials like suede or leather, or a sneaker cleaner for sneakers
  • Know your style and your wardrobe – can you picture shoes that are more an investment looking complementary to the rest of your wardrobe? Can you think of at least three different outfits where these shoes might work? Be honest…

comfy underwear

We’re entering a new realm, readers.

We never thought we would say this before, but… Are we about to recommend comfy underwear for men on Amazon? Yep. This is happening. 

There have been so many different kinds of men’s underwear companies that have come out recently, and quite frankly, who has the time to explore them all?  

See, in our minds, underwear is like a wallet. You need them to hold what you have. But at their core, they’re function over fashion.  

That doesn’t mean you should cheap out on your selection, but it does mean that “fashion underwear” may not be the best investment.  

Anyway, let’s dive into a few of our recommendations for comfy underwear:

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A few things to keep in mind when you’re browsing underwear options:

  • Stick to your style preferences – especially when buying new items, don’t decide to re-do your wardrobe down to your underwear. Keep it simple and stick to what you like
  • Don’t skimp on price – investing in quality underwear will make a difference. There are exceptions to the rule, but why cut corners on the most frequently worn garment you’ll have in your closet?
  • Keep climate in mind – should you be buying a more breathable fabric, or is that not as important given your daily whereabouts and activities? Ask yourself a few questions before buying to ensure you’re making the right choice 

an easy tee


Who doesn’t love a good tee?

The most effortless part of your wardrobe. With a soft tee, comfy jeans, good looking shoes, and cozy underwear, you can conquer the world.  

Classic t-shirts will never go out of style, so having them as part of your wardrobe is a sound investment. And by the way, we’re talking about sound, affordable investments. 

We should clarify that for the sake of this post, when we talk about tees, we are talking about t-shirts – not undershirts.

Undershirts serve as a functional addition, and aren’t a necessary component of your everyday wear (in most instances.) 

So, let’s take a look at some solid classic tee options:

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A few things to keep in mind when you’re buying t-shirts:

  • Try to stay away from workout shirts over regular cotton t-shirts. Usually, they’re made with different materials, and may appear a little too casual for office or drinks
  • Read the care directions – especially with t-shirts, you want to make sure that you’re not blindly popping them into the dryer. Depending on what the care instructions say, they may shrink. It’s just not worth it…
  • T-shirts are actually a fun way to diversify your wardrobe. If you’re having a casual jeans and sneakers day, different colors and patterns can help spice up an otherwise neutral outfit

a laid-back hoodie

men's hoodie

In our defense, we’re not entirely sure how else a hoodie is NOT laid back. Maybe if it’s cropped? Do they even sell those…?  

Anyway, hoodies are going to give you more of a casual look than, let’s say, a dress shirt.

But hoodies are such an awesome go-to comfortable addition to your wardrobe that we would be stupid to not include them in this list. 

Furthermore, when it comes to transitional seasons like fall and spring, hoodies serve as the perfect in-between.  

A few hoodie options we’re digging:

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Here’s what you should keep in mind when you’re thinking about buying a hoodie: 

  • Hoodies should be part of your go-to casual look. They’re not really meant for dressing up, but they can be used any other time
  • Try hunting down some fleece-lined hoodies if you live in colder climate to bundle up
  • We love hoodies in neutral colors – grey and black are the colors that you can recycle over and over again in your wardrobe 

a handsome jacket

men's leather jacket

Oh, YES. A gorgeous jacket is the icing on the wardrobe cake.  

Here’s why – when you have all of the elements pulled together, let’s say jeans, shoes, and a t-shirt, the one piece that pulls together your outfit is a cool ass jacket.  

And there’s so many different styles and directions you can head with a jacket.

You can go for a bomber on the weekends, a leather jacket for date night, and a trench for the office or offsite meetings. 

A jacket marries all of the cool items you’re wearing into one handsome look. We’re big jacket supporters. 

And here are a few jackets we’d recommend taking a look at:

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Keep these in mind when you’re considering purchasing a jacket:

  • If you’re looking to invest in one jacket vs. different jackets for different occasions, we’d recommend sticking with a leather (or nice pleather) jacket. Why? A leather jacket is grey area between casual and dressy. If you have a casual outfit on, a leather jacket will dress it up. Going dressy? A leather jacket can help make your look a little more edgy
  • As always, make sure to keep an eye on care instructions. Most of these jackets will require you to head to the dry cleaners
  • Keep sizing and length in mind – a bomber jacket on someone who is 5’7 is going to look a lot bigger than on a 6’3 frame – oh, did you say you were going for the cropped look?

a well-fitted dress shirt

men's dress shirt

Ah, yes. The dress shirt. The all important dress shirt. When perfectly fitted, some might even call it the transformative dress shirt. Men’s style can’t go without it.
When a dress shirt doesn’t fit, you know it. And unfortunately, so do the others around you (sorry, but it’s true.) However, when a dress shirt fits juuuuuust right, and works with the rest of your outfit, people tend to notice how slick you look. 
And let’s face it, you notice it too, because your shoulders are probably standing a little taller.
We think dress shirts are uber important to your wardrobe, which is why we wrote about them in our post on Classic Dress Shirts and Styling Tips. It’s worth a read if you want to get into the nitty gritty of dress shirts, how to measure for one, how to wear them, etc. 
But in the meantime, let’s take a look at a few different dress shirt favorites:

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Here are some things to keep in mind with dress shirts:

  • Fit is everything. Don’t guess what your size is. Do the extra homework to get measured for one, it’ll help you more in the long run!
  • If you’re building your wardrobe and buy your first dress shirts, start by investing in classic colors first like white, black, and navy
  • If you want to wear your dress shirts with jeans instead of slacks, go for it! We love this look paired with a belt and a leather jacket, too

Pssst – want more dress shirt inspo? Don’t miss our dress shirt 101 for more.

a sturdy leather belt

men's belt

Speaking of leather belts…! 

We are big on accessories, and one accessory we just couldn’t live without is a leather belt. Because a leather belt brings it all together. 

For some reason, if you’re ever seen someone with just khakis and a dress shirt, or a dress shirt and jeans, something always feels and looks like it’s missing.

Now you know why.

A beltless look can be a sad, empty look. Even if you don’t consider yourself to be a “belt person” (whatever that means) you should still have a belt in your wardrobe, given it’s a wardrobe staple and you never know when you just might need one. 

Here are a few of our belt picks:

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A couple of things to keep in mind when you’re browsing for men’s style belts:

  • A good leather belt will last awhile. Instead of pressuring yourself to buy multiple, start with one at a reasonable price point (~$50) and go from there
  • If your belt does start to fade, it doesn’t hurt to use some leather conditioner to keep it in tip top shape

a relaxed hat

man's hat

A good hat seals the deal.

Not as much as a jacket, if we’re being honest, but it’s a warmly regarded accessory that definitely deserves a top spot in your wardrobe.  

Let’s chat briefly about different types of hats for men, and why they’re a men’s style staple.

There’s the beanie, the fedora, the driving hat, the baseball cap…! 

Our favorite hat wearer in the media right now is Karamo Brown, who pulls off a bomber and baseball cap SO well. Talk about a man who knows his style to a tee. 

Alright, so let’s get to the good stuff. A few fun hat options for your viewing pleasure:

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And a couple of things to keep in mind when purchasing a hat:

  • Know your audience-ish – a fedora is great for vacation, but might be a little awkward at work. A baseball cap might be too casual for work. Whether or not we agree with current business dress norms, it’s worth noting that some hats just may not be meant for the workplace
  • Hats are a cheaper investment compared to other items on this list. It’s a great opportunity to accessorize with hats as an east way to change up your look

breathable shorts

man wearing shorts

Drumroll please…our 11th and final item to this men’s style list might come as a surprise! 

Breathable shorts can make all the difference in a warmer climate or a day out in sunny weather. And they’re always great to have on hand for last-minute vacations.  

What exactly do we mean, then, by breathable shorts? We’re talking about shorts that have moisture-wicking fabric or are made of linen fabric, which also helps keep the skin cool.  

Here are a few options we love:

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And some things to keep in mind when buying men’s style shorts:

  • Unlike other items on this list, shorts are truly seasonal. Which works out well heading into the winter season right now because everything is on sale, so it’s a good time to build up your wardrobe
  • Keep in mind short length – if you like your shorts shorter, more power to you. But not all shorts are created equal (in length) and before you order, you’ll want to check out the inseam
  • White shorts might be harder to keep clean, so if you’re considering investing in shorts, try a black, navy, or even khaki first

Final Takeaway: 11 Timeless Basics Every Man Should Own

If we had created this post 5 years ago, or 10 years ago, we don’t believe the items listed here would’ve changed.

We truly believe that each piece mentioned here is truly timeless, and they’re the items we’ve found ourselves revisiting in our closets over and over again. 
If your focus is on having timeless items in your closet, then let this post guide you toward starting to build your ultimate timeless wardrobe. And with that said, we’re always open to suggestions.

Let us know what your timeless items are in the comments section below.

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