Casual Mens Clothes Shopping Adventure

I recently went clothes shopping with a male friend who has little (read: almost no) interest in fashion. Sure, he cares about how he looks -- something he lacked when we met as teens, though has happily grown into in his 20s -- but he was clueless about where to get clothing or what to try on.

Thankfully, he was an eager and willing participant when it came to trying on plenty of clothes during our shopping adventure.

Over the course of two days, we went to several affordably-priced retailers with heaps of men's clothes. We saw it all -- from shirts labeled "medium" that looked more like XXL at the regional department store Bon Ton, to turquoise, acid-washed men's skinny jeans at Pac Sun.

Despite its poor size selection, Bon Ton was still the first place he made a purchase: a pair of Calvin Klein jeans with a low-rise waist, straight leg, medium wash. The pants have a grayish/rusted wash which is stylish but subtle. And they are cut much less baggy around the hip area than most of his other jeans, making them significantly more flattering to his physique.


The next day he got a black button down shirt and a plaid short sleeved button down at Sears. Pretty standard fair, but keep in mind we were looking for additions to a wardrobe largely comprised of polo shirts purchased by his mom and screen print tees that went out of style after high school.

The patterns on these shirts look more subtle in person, I took the photos in a dark room so the colors are skewed.

(This would look great with a suit jacket and jeans.)

(Dark jean friendly -- didn't look as good with the new CK jeans, since it was too gray all over.)

Finally, we hit the jackpot when it came to our main quest for the trip -- t-shirts. My friend wanted casual t-shirts he can throw on to go to school instead of wearing one of the aforementioned polos every day. (He says his screen print tees are relegated to in-house wear and don't see the light of day. Probably a wise move.)

And we found them at (drum roll please)...Old Navy. Five dollar tees that look awesome and feel awesome.

For $25 he left with five well-fitting, attractive, versatile shirts. In black and light gray he got this classic tee with a round neck, though it's also available with a v neck.

My favorite shirt though was this ringer tee with contrast trim that he got in greenish turquoise, charcoal gray and navy blue. It feels soft and really makes the shoulders look broad. I think it's one of the most flattering, effortlessly cool things I've ever seen my friend wear.


And to think he was relucatant to go into Old Navy! It typically isn't the first store I hit either, but from what I recently saw, I think their quality has significantly improved in the past few years.