CM regular and well-dressed dude @Chocsosa is 6’8, which you may remember from his member focus. We asked him to share some of his tips for dressing well when you’re tall, and he obliged with both personal insights and some good rules to follow.

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Starting out trying to build a functioning wardrobe of your dreams is not for the faint of heart. That is one of the first things I came to realize when I started this journey 15 years ago. Of course, things were very different for me then. Information was not as free flowing as it is now in relation to the nexus of style and quality.

I made a lot of mistakes early on trying to figure out what worked for me. To be honest, I’m glad I made those mistakes, because it was a journey I needed to take to figure out who I wanted to be. I know that it sounds very cliché but it’s interesting right now that I look and certain looks and think to myself: “You know, that looks good, but that’s not for me. It’s not something I would want to wear for myself.”

It takes time to get there. However, when you do get there, to me it’s sartorial nirvana. You are comfortable in whatever you are in because it works for who you are – and in the process, you save yourself money. For me, it was a relief to figure out what worked for me and dress down my height as much as possible. I know, tall people problems. However, this is something I struggled with for a very long time.

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Measurements

it’s hard for tall people. I would trade my height in right now for something shorter if I could, because it’s more of a deterrent than a help. Cars are never big enough, long flights are always a pain, stares can be annoying, and clothing can be a lesson in futility if you don’t know what you are doing.

First thing I suggest is really know your body in terms of measurements. My brother in law will run purchases by me from time to time. He does not know the intricacies of online shopping, so he will see a blazer in his supposed ‘size’ and he will purchase it. The said blazer arrives and it is either too tight or too big all over. He is learning that every label has their interpretation of varied sizes and the only way to navigate that craziness is to really know your measurements and check the listed measurements being sold online (whether on Ebay or an online site for a label). If a seller does not put measurements then I ain’t buying. That mantra has saved me money the last couple of years.

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The Financial Investment 

Saving money is a wonderful thing, but understand that with height come certain financial realities. I love a deal when I get my hands on one, but I also understand that most of those deals are not for people of my size. It kills me to scour Ebay to see something in my size and then look at the measurements and see that the inseam is nowhere near what I need it to be to work.

Never compromise on this. I promise you that you will regret it. With that out of the way, you must understand (if you are really tall, like over 6’3), a lot of the time you are going to have to pay the price on a NWT item. I have a 38-inch inseam and I love me some cuffs on my pants. This means I must find a pair of pants with an inseam of 44 inches. Do you know how hard that is? I will rarely get that with a pre-owned item. That’s why I thank my lucky stars for Ebay. I may not buy a lot of pre-owned items, but I am able to get a high end RTW item at a huge discount versus going into a store and trying to purchase them. When I do find a pre-owned item that’s within the parameters of an acceptable fit, then I have my tailor work on it to make it work for me.

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Tailors and Tailoring

Knowing what you want out of tailoring and having an awesome tailor is key. My size presents a whole host of issues when it comes to tailoring and tailors in general. I’m 6’8. I have broad shoulders and a somewhat barrel chest. I have a 9 inch drop and long limbs.

When I was searching for potential tailors it was tough, because I had tailors trying to force their view on how something should fit on me which would go against what I saw for myself. You have to stand your ground and tell them that they can either help you achieve what you are looking for (as long as it’s do-able and in somewhat good taste) or that you’ll keep looking. However, you also have to understand the boundaries of tailoring for your height. My tailor always says it’s better to take in than to let out. What this means is I have been able to re-cut a suit from a size or two up down to my size, but it’s virtually impossible to take a suit from a smaller size to make it a size bigger.

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Silhouette

Silhouette has also played a huge role in what I look for in clothing. The silhouette that I go for differs between what kind of clothing I am looking at, but each article of clothing I pick has to look the way I want it to look for myself. Suits/sports coats are usually a mixture for me. For the most part I am partial to a structured look (strong shoulders, built up chest and nipped waist) but, when it comes to sports coats, that can differ. Soft or structured does not matter as long as it works for my body.

When I am looking at outerwear pieces, then that’s pretty simple. I like a higher armhole and a slim profile. The main problem I run into is sleeve length, and that’s where patience becomes a virtue in the search for something that fits. A short jacket does no favors for a tall guy, but a long jacket can make a fit look a little less contemporary. So I always try to find the middle ground when it comes to jacket length. I also favor a slightly lower button stance. I think with a somewhat longer jacket it can do wonders for a tall frame.

It really comes down to how you want to build your wardrobe. Your mental image of the tall person you’re trying to bring to life should encompass your personality, your emotions, and how you see yourself. You have to keep in mind, however, that it’s a journey, and you are going to make some costly mistakes along the way. If you are committed you will eventually get where you want to be with your wardrobe. That’s been true for me, and I am still learning something new all the time.