A guy walks into a restaurant wearing a midnight blue suit. While at a distance he looks pretty good, you begin to notice slight flaws in his outfit the closer he gets to you. His jacket sleeves are a little longer than his wrist. His pants go slightly past his ankles. There appears to be a little extra room in the chest area which makes the jacket appear a bit baggy. It is apparent that his suit does not fit him well. What do you think?
If you would think nothing, I think that wouldn't be an uncommon response. You probably wouldn't spend more than a moment or so thinking about him, and here's why:
Wearing nice clothes that don't properly fit is akin to wearing casual, i.e. average, clothes.
So just like you might briefly notice the person on the subway wearing bright neon pink running shoes, you most likely will only spend a brief moment thinking about the person wearing a suit that doesn't fit. You actually might assume that they're new to fashion or that they don't dress-up often; either way, the guy wearing the ill-fitted midnight blue suit won't attract much attention.
Now picture this: another guy walks into the restaurant. This guy is wearing a pristine charcoal three-piece suit. The fit is immaculate. The jacket sleeves rest slightly above the wrists showing the cuffs of his bright white Oxford shirt. His pants rest a bit above the ankles showing just a bit of his dark black socks. There is no extra room in the chest area of the jacket. This guy is the sharp as a tack. What do you think?
I would guess that you would think a little more highly of this guy. You might even admire his style and take a couple more glances at him after he's seated. No, you won't gawk at him, but the fit of this guy's outfit will make him stand-out and cause you to think about him a bit more than the first guy. You might assume this guy has a powerful job or that he's someone respectable. Whereas you thought the first guy was a fashion amateur you might think the second guy is a professional. He knows what's up. He knows how to get attention and demands respect with his confidence.
You see, in my opinion, proper fit is the most important part of dressing-up; if something doesn't fit properly, you might as well not wear it because it's not going to convey the message you want. Now, I'm not saying you need to have every article of clothing you own fit you perfectly, but you should make a serious effort to get clothes that fit you very well.
When I first started dressing-up, I didn't know much about proper fit, and honestly, I didn't try on different sizes. Rather, I found a jacket that sort-of fit me, and just decided to go with it. The fit of my first suit was essentially that of the fictitious guy in the first paragraph, only it was black instead of midnight blue. It was a size 40R which was a bit too long. I also bought a pair of pants that were 32x32 which were a bit too long as well. I didn't look great and more importantly, I didn't feel it because I was aware that the fit wasn't perfect. However, despite knowing this, I thought that a 40S would be too short, so I stuck with the 40R for my next couple sports jackets.
It wasn't until I found a tailor that I discovered that my size was indeed 40S. So I had my few jackets and suit altered, and from that moment on, I bought suits that were 40S and pants that were 32x30. Let me tell you, after getting my clothes altered, I felt a whole lot more confident.
I highly recommend finding a great tailor. Having a good relationship with someone who specializes in things like proper fit and fabric can be quite beneficial when you're just starting out. While it's not compulsory, knowing a great tailor can help you bypass a lot of the issues I experienced early on. It's analogous to working with a fragrance specialist at a department store to find your signature scent.
A huge part of having a tailor is knowing your proper measurements. Understanding your measurements can be incredibly helpful when shopping for suits or dress shirts. Consider that many luxury dress shirts are sized by your neck size and waist size. For example, my favorite white Ralph Lauren Oxford shirt is size 15" 32-33. It's strange at first, but keep in mind, that traditional sizes-- i.e. small, medium, and large-- are for more casual/cheaper pieces of clothing.
But what if there isn't a tailor near you? No problem. These days you can get your measurements from many different department stores including Mens Warehouse and Nordstrom. Simply ask an associate if you could get your measurements. A lot of these places offer in-store tailoring as well, which makes knowing a specific tailor not necessary.
So whether you have a go-to tailor or not, knowing your proper size ensures that you can get the best fit possible. As I said, you don't always need to find the perfect fit, but it should be as near perfect as possible. That's what is going to get you the positive attention you want. Be the guy in the charcoal three-piece, not the guy in the midnight blue.
-Ryan S.
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