When it comes to clothing, guys are pickier than you would think. But what we're looking for is not so much color and style per se, but more about comfort. Now that is a loaded term, so let me name three characteristics of comfortable clothing:
Everyone - meet Ben. He's a 20-something software engineer whose uniform generally consists of a punny humor tee and the same trusty pair of jeans that he's been buying from the same store for the last 15 years.A few months ago, Ben's girlfriend asked me to go clothes shopping with him. I didn't think much of it at first, but when she brought it up again I knew that she was serious. I'd never gone shopping solely to help someone else clothe themselves, so I wasn't sure exactly what I'd be doing. But I thought, what the heck, it sounded like fun! We hit up Nordstrom Rack on Saturday afternoon. Ben told me he wanted to upgrade his look, and on his list were shirts (casual, going out and formal/dressy), plus a good pair of jeans. Yup. This was definitely going to be fun.
We took over a dressing room while I kept pulling things off the racks and made him try them on. The jeans were surprisingly easy to find - Rock and Republic had a great pair of straight jeans that fit Ben like a glove. The shirts took more time, but we eventually found a sweet spot. Ben likes interesting patterns, and having an assortment of t-shirts has made him open to colors. The key with the shirts: not giving up after the initial fit didn't work. We made friends with the in-house tailor and had him pin the shirts a bit. We looked at shirts with darts and shirts that took the seam in altogether and...voila! Shirts that fit color, pattern, and cut criteria, all in one!
I ran into my friend Brian at a party and had to snap a picture of his T-shirt because it was so cool. He got it in Japan. Figures - get another example of their indisputable design prowess. Yes, it says "T-shirt."
In general - I like patterned dress shirts more than solid colors. Mostly because they're more visually interesting - especially since the dress shirt generally plays a supporting role in any given ensemble (under a suit, sweater, etc.)
Not to take away from a clean, crisp white shirt but sometimes you want something more fun - like this light blue checkered shirt a la Paul Smith. I wasn't the biggest fan of this pattern at first because it reminded me of a picnic blanket - but it's grown on me with more stores taking hold of this trend and playing with the size and color of the checks.
Paired with a light grey suit it would be dressy enough to wear to work (if you need to wear suits to work). One note of warning - I've seen guys try a bowtie with this pattern and unless you are incredibly British (think Prince Charles) it's really hard to pull off. Stick with a fairly muted (meaning not large print or crazy paisley pattern) or no tie at all.
My favorite look with this shirt - pair it with a darker pair of jeans and a dark chocolate brown tie. Many options if you need to layer for warmth - my personal choice would be a more casual black blazer (but you can go with a grey cardigan or a golf jacket of any color that is gaining in popularity these days).