Meet People Chicago Blog

Men's Easy Style Guide (How to Dress Sharp): Part 2 - How to Dress to Impress

Welcome to part deaux gents, this is what you really came for.

At this point, you know why you should invest in some nice clothes. You understand that dressing well implies many things about your character, your personal brand and your level of confidence. But what you probably don’t understand yet, is HOW to dress with some style. And so here you are.

I understand that it absolutely can suck to learn about fashion and spend hours at the mall guessing what looks good, so I aim to make this as SIMPLE as possible for you. I’m going to give you a quick lesson on style, links to different clothes essential for every man and exact outfits to wear...the whole enchilada with some extra sour cream on the side. Yum.

Style 101

I feel there's a huge misconception between men on what style actually is. It's pretty critical you understand what it means to have style, because if you misunderstand, none of this will work.

Style is something each of us have, something we cultivate through our lives. It’s unique. It changes as we change. It’s the colors we like, the way we walk, the things we say, the ideas we believe. Clothes only amplify this and allow you to express your own unique style more easily. See, I like crisp blazers, a strong tie and a nice watch, but that’s me. Many men have a similar style and many others could care less for any of those and that’s fine. Just go with what you like. Whatever catches your eye. Be you and embrace it. Kinda hippie sounding, I know. But the thing about style is that if you just copy with no passion and don’t have your own little taste added in, then it’s not authentic. And inauthenticity is not only a huge turn off, but it won’t work. The best I can do is give you an idea of what to wear and you take it from there. How? Well, check out one of the examples below and if something catches your eye or you like a certain item of clothing, boom, that’s authenticity. You didn’t just choose the clothes below because it’s what I recommended, or what everyone else is wearing, it’s cause you could see yourself in them, rockin’ it. That’s style.

The Best Places To Shop

All malls have hundreds of different shops. The number of choices we need to sift through can be mentally draining so let me help you out by narrowing it down to the best place to shop for men. We have a wide range of variety here that all deliver some great style. Start filling up your closets with these shops.

Hugo Boss

This is the brand if you’re comfortable throwing around some cash. I understand not everyone wants to spend a huge amount of money, so if that’s you, scroll below. For those of you who have some extra cash, I highly encourage you to look into Hugo Boss. The fit and the quality are worth the money.

IndoChino

If you’re looking for a reasonable place to buy quality blazers and suits, look no further than IndoChino. They have absolutely amazing price points for the quality they offer. First, you’ll have to do the initial work of figuring out your measurements so grab a tape measure and head over to their quick tutorial on how take measurements here. Once done, head over to their blazer and suits sections and scroll through.

Express and H&M

I want you to realize that although Express and H&M may be less pricey, they're not as high quality. A blazer from IndoChino or other outlets with a higher price tag will last you longer. So although you’ll buy a blazer here for less, you may be buying one every year as opposed to buying just one that will last you for a while so you’ll actually be spending MORE. Also, both outlets are more for fit dudes.

Banana Republic

This is the outlet for you if you’re looking for a in-between place. Not super pricey, but not cheap either. BR is great medium because they have very in-style clothing and cover everything you would need. It’s definitely a one-stop shop for classy meets affordable.

A&G

You know, you really can’t tell one denim from another at first, but you sure can feel the quality of denim, and A&G delivers in that regard. Although pricey, these jeans will last you for a loooonng time. They’re known for their jeans, but also deliver on khakis and chinos.

Bonobos

Bonobos is my go-to place for chinos and khakis, it’s a cut above the rest and they deliver a great product. Bonobos know’s how to make quality pants for a decent price. You have to spend a little bit here, but well worth it in my eyes.

Burberry

Imported from London, Burberry is definitely upscale clothing so don’t expect to spend anything less than $100 here for any of their clothing. Crisp clothing, unique style and a brand that makes people look twice. You’re buying more than quality here, you’re buying the brand and on some occasions, it’s worth it.

The Essentials for a Man

Let’s work our way from top to bottom. I’ll list from high quality (Upper Tier) for each item to low quality (Bottom Tier) so you have a broad range of choices. Click on each picture for more details. Without further adue…

Blazers

Ahhh my personal favorite: blazers. Blazers, or sometimes called ‘sport coats’, are an absolute essential for every man so I’ll go into plenty of detail on this one. A nice blazer will do wonders for you, trust me. The biggest thing that will stop you from buying one is the price tag. Yes, they’re a little pricey, but think of this as an investment. Measure its return on how you look and feel wearing it, that’s how the investment pays off. Ideally, you want all sorts of different colors in your closet, but start out with buying the classics: black or blue. Get one of both colors and you can wear it with anything in your closet, then build up from there. You don’t need a ton of blazers, 1 or 2 is perfect to start out.

Upper Tier

                                                                    

Mid Tier

                           

Bottom Tier

      

The Undershirt

This one goes without explaining, so I won’t go into details here, but keep in mind that you want something that you can wear underneath your blazer as well as without one. Many different types of undershirts exist and you can buy them from anywhere but I’ll recommend Burberry for high quality, Banana Republic for in between and H&M for the least expensive.

Accessories: Watches and Pocket Squares

Congratulations, so you’ve picked out a blazer and a nice shirt. You are literally leagues ahead of other men, but take a step further with an accessory or two to add some flare. You can find both of these items at any of the outlets I’ve listed above, but here are some specific picks I have for each.

Watches

There are a TON of different styles of watches, but for our purposes, we’ll concentrate on dress watches. Dress watches come in two common styles: leather strap and metal bands. Ideally you want one of each and to try to match the shape of the watch to what you physically look like. A thin watch will look odd on a bigger person for example. Also, you want to make good matching choices with your shoes and the rest of your outfit---generally, metal bands go great with suits. Leather bands go great with matching shoes and denim. From most to least expensive we have, Movado for the best, Fossil in the mid price range and Timex for least expensive.

 Upper Tier

         

Mid Tier

                 

Bottom Tier

                           

Pocket Squares

Pocket squares are definitely a nice touch to any suit or blazer. If you match it well with your undershirt it’s going to be an absolute hit. There’s a few ways to fold them, but here are the most common three: the puff fold, the straight fold and the one corner fold. It’s really up to you which way you want to fold the square. You can get a pocket square pretty much at any outlet, the quality isn’t a huge deal but check out Men’s Warehouse for a HUGE variety and decent prices. Here’s a pic of each style in order as listed above:

            

Bottoms

We are below the waist now, nearing the end here. Not incredibly much to cover here. There are only two types of pants that concern us: chinos and denim jeans. Get a couple of each type and you’re set for pretty much any occasion. The important part here is that you get pants that fit well on you. Not too tight and definitely not too loose. Like in the above sections, quality and price are related, and by now you know where to shop for whatever you’re going for. High end brands for chinos are Bonobos and A&G for denim. Both these brands are solid choices, but pricey. Otherwise, look at Banana Republic, Express and H&M.

Shoes

A lot of men think that shoes don’t really matter. That’s wrong for a plethora of reasons! First, you walk around a LOT. The wrong type of shoes will cause some major issues for you in the future. Secondly, you know how women have closets full of shoes? Well what do you think they look at on a man when they first meet him? That’s right, his shoes.

We have lots and lots of awesome brands to choose from here men, I had to narrow it down to just a few...which was difficult. Let’s take a look each tiers brands:

Upper Tier - Magnanni, Santoni and Aquatalia

Mid Tier - Cole Haan, Calvin Klein and Andrew Marc

Bottom Tier - Bostonian, Steve Madden, Clarks

When looking at brands, what you want to invest in is comfort and style. There are quite a few different types of shoes that you want to look at and acquire over time but we’ll focus on boots and dress shoes.

Boots

For boots, let’s look at chukka boots and dress boots. Chukka boots are sort of a hybrid between a boot and a shoe. They go up to your ankles and are usually made with leather. Dress boots are go up further than your ankles, have many more lace openings and are also usually made from leather as well. Both boots are great, depends on your choice of what you like better. Let’s take a look at examples of each, chukkas first.

Upper Tier - Chukkas

Mid Tier - Chukkas

Bottom Tier - Chukkas

Upper Tier - Dress Boots

Mid Tier - Dress Boots

Bottom Tier - Dress Boots

Dress Shoes

Dress shoes comprise of many many different types of shoes: oxfords, loafers, derby, etc. Lace-ups and loafers are the most common worn. Lace-ups are something you probably have in your closet right now, just regular ole' dress shoes. Loafers have no laces and are more relaxed. Let’s look at the lace-ups first.

Upper Tier - Lace-Ups

Mid Tier - Lace-Ups

Bottom Tier - Lace-Ups

 

Upper Tier - Loafers

Mid Tier - Loafers

Bottom Tier - Loafers

Stylists

If you’re still a little overwhelmed, there is help if you’re willing to spend a little (by a little, I mean a lot!) on stylists. The good thing is that once you understand how this works, you can do this by yourself if you choose to. Nordstrom has a stylist in house who helps you re-invent yourself. I’ve used their services and it’s pretty damn good. The stylist is very helpful in determining your style and answering any questions you have. They pretty much do this guide in person and help you choose your own style. Check them out here. If you want an even more personal stylist, check out Trunk Club, a company dedicated to matching you with a personal stylist who assists you 24/7, all year round. They even have a blog that is really awesome and keeps you up to date on style. It’s a fantastic service, especially if you’re looking for a unique experience and super personal service.  

Wrapping It All Up

There you have it, top to bottom, I’ve given you reasons on why you should care about your appearance, great brands, popular and stylish choices for each piece of your wardrobe and tips on how to dress sharp and impress. Mix and match all of these pieces and you will get a wardrobe that is sure to turn heads. Don’t be surprised if you start acting differently. Don’t be surprised if you start walking differently. Don’t be surprised who you start talking to --- beautiful women, successful professionals.

I guarantee you’ll notice a change.

Cheers,

Sam Amir | Superhost | Meet People Chicago 
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