A Beginner's Guide to Menswear

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I’m still a t-shirt, hoodie, and jeans type of guy, but regardless of the event, I feel most confident in my best suit. A good tailored suit can make a difference of night and day. However, this wasn’t always the case for me.

When I started working in men’s clothing, it was obvious that I hadn’t updated for a while. My “suit” was an old tuxedo jacket and pair of khakis that were frayed at the break. My shirts were too small and I only had two ties that I knew how to tie, but didn’t bother to. I just loosened them and threw them aside; they always looked sloppy. My shoes and belt didn’t match, my polos were either fading or had holes in them, and with my jeans, the overall shade was too light on one pair and the other was very baggy. I was not a pretty sight. I only got hired because a friend worked at the store, the manager needed people, and I’d recently graduated college and needed a job.



I still don’t consider myself a subject matter expert, but I have learned a lot working in menswear. I’ve had customers in their forties and fifties who have never had any tailored clothing before. And earlier on, someone asked Are sweatpants OK to wear on a first date? As my dad would say, if you want to be single for the rest of your life, the answer is “no”.

Your transition should be gradual and this YouTube Video - "The Big Bang Theory - Sheldon Goes Suit Shopping" - can be a guide. Let’s get started..

1. Slacks

If you’ve never owned tailored clothes before, this is a good starting point. Start with one black pair and a navy pair with pinstripes. There are pleated and plain-fronted pants. I prefer pleated.

Cuffs are the recommended hem on pleated pants. Note that dress slacks are worn higher up than jeans, so the waist is usually about two to three inches larger. My jeans are a 32-inch waist, but my slacks are 35s.

2. Suits

The recommendation is to have at least two suits; one black and one navy. If you feel particularly confident about your choices, try a pinstripe or basket-weave pattern. I recommend suits from specialty stores that require tailoring because you have more flexibility with the final look and feel. Most specialty stores charge for alterations and usually have a two-week turn-around.

Suits are measured by chest size and will carry generic pant sizes. I wear 41 long suits which come with 35-sized waists. 42s come with 36 waists, 40s with 34s, and so on.

3. Dress Shirts

Start with a solid white shirt, a solid blue (French blue is my favorite) and one other color of your choice (never be afraid of pink!). I recommend spread or pointed collars, so buy extra collar stays. If you don’t know what those are, there are little slots on the shirt’s collar where plastic tabs are placed to keep the shirt looking crisp. Spread collars square off better with jackets.
"Wrinkle-free shirts cost more, but will save you money in the long run on dry cleaning!"
Wrinkle-free shirts cost more, but will save you money in the long run on dry cleaning. Every half inch in the neck adds inches around the waist, so make sure you get measured correctly and select the right cut for your body type. I wear a tailored-fit 16 ½ x 35; the shirt is a little more tapered, my neck is 16 ½ inches around, and my sleeves are 35 inches long.

4. Ties

Your tie should blend with your shirt and jacket (if you’re wearing one). I think this is much easier to do with a solid shirt. When in doubt, wear a white shirt with a solid-colored tie. My favorite designs are slanted stripes and paisley. Buy a tie clip to keep it in place. The tip of the tie should sit either just above your belt line or over the belt buckle.

5. Jeans and Khakis

Have three pairs of jeans: one regular shade, one dark, and one faded. Wear the blue and faded for everyday use, blue for business casual, and the darker pair for a night out. Faded jeans can also be good for the evening, but this depends on the overall shade. For khakis, I recommend having at least one tan pair. They are worn the same as dress slacks.

6. Casual Shirts

Button-down collars look better here, but are not mandatory; spread or point collars look good as well. Pick lighter colors for an out-and-about look during the day and darker colors for the evening. Wear a crew-neck undershirt during the day and a tank top for evenings.

7. Sportcoats and Blazers

I prefer sportcoats over blazers because, in my opinion, they are more versatile. Depending on colors and patterns, they can match a shirt and tie, business casual, or casual look. Spoartcoats have different textures and patterns. Blazers are suit jackets with different buttons and work better just for business casual.

8. Socks, Shoes, and Belts

Your shoes and belt must match. Your socks should match your shoes with jeans and khakis. With suits, they should match your slacks. I prefer loafers or other slip-ons.

Polish them regularly. Your belt should be one to two inches larger than your waist, but this applies to both jeans and slacks. My jeans and slacks are 32 and 35 respectively, so I wear 34 and 36 belts.

9. Touching Up

If you remove the tie and undo the top one or two buttons on the shirt, a necklace of some sort is a good complement to a suit. Wear a lapel pin and your high school or college class ring for identity, but also for networking. For final touch-ups, I use Axe hair cream, Axe deodorant, and my selected cologne is Bleu De Chanel. Lastly, wear a watch.
"When you wear a good set of tailored clothing, you see a whole new side of yourself."

KNOW THE BUSINESS!

Menswear is expensive and if you add alterations, we’re talking about a fairly large investment. Depending on where you go, plan on spending no less than $500 or $600. However, consider the value you want and where the better sales are. Jos. A. Bank’s signature sale is Buy One, Get Two; buy one suit at regular price and get two more of equal or lesser value free. Sometimes, it’s the entire stock.

You can do a mix-and-match, so if you have friends who need suits, pool your money and get the deal together. K&G has picked up the Buy One, Get Two and Men’s Wearhouse runs a Buy One, Get One sale.

When you wear a good set of tailored clothing, you see a whole new side of yourself. If you feel strange trying out your new look, play Bad To The Bone in your mind. You’ve probably heard that what’s inside is what counts. This is true, but how you present yourself draws even more of it out. I can tell you from personal experience that this confidence will stay with you even after you change. Though it may take some time to absorb, it will become apparent. And the most important note of all: you’ll look awesome!
A Beginner's Guide to Menswear
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