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After years of school surviving on Vans, shorts, and t shirts, how does a guy entering the so-called real world dress well? It’s an interesting question, and unfortunately it’s not a class offered at most colleges. The art of dressing well is an important issue, because unless you are Mark Zuckerberg, you probably will need to upgrade your wardrobe.

Clearly, I needed some help

I know that this was, and continues to be, a learning experience. Growing up, I was not making any best dressed lists. In elementary school, no matter how cold it was, I insisted on wearing t shirts (granted, I’m from southern California, but still). Until my junior year in high school, I refused to wear jeans unless my parents forced me to for Christmas pictures. During high school I got caught up in a love of rap and hip hop and decided to wear clothes more aptly suited to a full grown mountain gorilla (combine this with puberty and a growth spurt I hadn’t adjusted to, it’s no wonder I struggled in courting any of the fairer sex).

Even during college, when I started to wear clothes more suited to my body, no one would put me anywhere near a GQ cover. Many an 8am class you could find me rolling in 5 minutes late dressed in sweats, a t shirt, and a backwards hat. I could clean up a little bit if my friends and I were going out or if I had a job interview, but otherwise I was completely clueless. It makes sense though–I’m from Orange County, where the accepted dress code is shorts and tank tops, or if we feel like classing it up, jeans and a t shirt.

But then I got a job with Citibank, where if I showed up in a t shirt, they would spin me around 180 degrees, hold the door open for me, and tell me to find a new job. Clearly, it was time to spruce up my wardrobe, but I still knew nothing. I had to learn, and learn fast.

I knew I wanted to dress well, but as a recent college graduate, I wouldn’t be buying the latest Armani suit anytime soon. So, the issue was how to dress well on a limited budget.

Thankfully, it’s possible. If you can’t afford top of the line Brioni or Tom Ford, you can still look like you belong in the boardroom.

First, you need to know where to shop. I have a few favorites, although certainly more exist. One of my go to’s is Nordstrom’s. Now, if you are familiar with Nordstrom’s you are probably yelling that it’s definitely out of your price range. Not so, young padawan. There is a beautiful little event called the Men’s Half Yearly Sale. It occurs twice a year, in June and right after Christmas. This means that you can get top of the line items on the cheap, and often for half off.

My first experience with this glorious event was a little over a year ago. My first in person interview with Citibank was coming up, and I didn’t have a true suit at that point. My dad took me to the sale, and we got a Nordstrom’s brand suit that normally ran at over $700 for about $350. It was an absolute steal.

The reason I love Nordstrom’s is two-fold. On the one hand, they have quality items. A suit or coat from Nordstrom’s will look good and will last (yes, it can be expensive at full price, but that’s why you wait until the sale). On the other hand, they have phenomenal customer service. Shopping there is so easy. The staff is helpful and knowledgeable. They will steer you in the right direction and make sure you get what you need. The return policy is painless. If you need a little more hands on assistance, you can sign up for a free appointment with a personal stylist. And possibly the greatest thing is that many of your tailoring needs are free (we will get to this in a little).

My other favorite place to shop is Suitsupply. Suitsupply is a clothing company that I first learned about this summer while in New York. I was reading GQ and ran across their name and found out they were located about 30 minutes away from my hotel. I looked them up online and, while researching, found a Wall Street Journal article that stated Suitsupply suits were nearly identical in quality to Armani suits. The only difference? An Armani suit costs about $3000 more. Right then I was sold. I went and visited the store in Soho and picked out a navy blue suit that cost me $469. Yes, it’s a little pricier than many young men may want to spend, but for the quality it’s worth it (I am looking forward to getting another one soon).

Suitsupply Store

While Nordstrom’s and Suitsupply are my primary shopping destinations, other options exist. If you are fond of online discount/deal shopping, check out Gilt/Park and Bond. They offer discounts on many name-brand items. I also know that many of my friends shop at Jos. A. Bank and Charles Tyrwhitt. While I don’t personally go there, I know many people who speak highly of them. They usually have deals going on such as 4 shirts for $199.

A quick note. These locations apply to casual clothing, not just business clothes. I routinely shop at Nordstrom’s for jeans, jackets, t shirts, etc., and I know that the other places have casual clothes as well.

So now you know where to shop, but you aren’t exactly sure what to get or what looks good. That’s not as easily answered, because much depends on where you work, your body type, and personal preference. For instance, I am tall, lean, and in banking, so what I wear is going to be different than that of someone who is short, thick, and in advertising. It depends.

That being said, do your research. I love reading magazines like GQ and Esquire. While I can’t usually afford the pieces they are showcasing, the magazines help me develop my sense of style, what I like and what I don’t, and what to look for. I also read online blogs and magazines like Primer and Art of Manliness. Here are some of my favorite places to learn:

Whatever you decide to go with, I have one piece of advice. Get it tailored. I can’t stress this enough. A $100 tailored suit looks better than a $3,000 baggy suit that doesn’t fit. Spend a little extra and make sure you look good.

No matter where you go, dressing well matters. This gives you a good place to start. Dressing well is an art, not a science. It also takes time. It also feels good when you stroll into the office and colleagues comment on how well you look, or even better yet, beautiful girls on the street. I have a couple of tailored suits, and nearly every time I wear them someone compliments me. It’s a great feeling.

I am living proof that anyone can go from the worst dressed in high school to dapper gentlemen. I went from wearing glorified tents to best dressed in the office. Truly, if I can do it, so can you.


Do you have a friend who needs to dress better but doesn’t know where to start? Then share this post with them.

Images courtesy of me, Joe M photoRogier Noort, and Primer Magazine.