The first job I landed out of college was a concierge in a luxury residence in Boston. We had a uniform of dress pants, dress shirt, tie, and a jacket. We could do a lot with that, there was no official uniform, but I choose to blame that job for the reason I really dislike wearing the whole kit and kaboodle. I rarely need to dress up anymore, but when I do, I do it a little bit rockabilly.

The jacket is from H&M and I love the cut of it — it’s slim without being too tight, due mostly to the very high armholes. It’s hard finding jackets off the rack that are cut like this, so I snapped it up immediately a few years ago. I’m a fan of the single button silhouette, since I’m a slimmer guy and the more simple things are the more flattering they look. Double breasted suits and too many buttons end up making me, and most guys, look boxy and like a needleneck. Ain’t nobody got time for that.

Instead of the dress shirt I went with a tank top. It’s more comfortable for me, and I like the pop of skin under the jacket — just because you’re dressed up doesn’t mean you need to be covered up, it’s just how you do it that’s important. The shirt is actually a dark navy blue, which I thought added a nice subtle contrast with the black/grey in the jacket, and the olive of the trousers.


Further going with the rockabilly idea, I decided to wear a pair of bracelets that I had.  One is a metal ball necklace that I wrapped twice to use it as a bracelet, and the other is a studded leather bracelet from Forever 21 that I picked up for about $5. Something different, and it’s a nice alternative to a watch.


Playing off of the black and grey of the jacket, I went with my trusty penny loafers, though ask me in public what they’re called and I’m going to call them “boat shoes.” I got these for $9 on sale at Urban Outfitters a year ago or so, and they’re super comfortable and take me everywhere. I like how they’re super easy to just slip on, but they still add a bit of polish to a look. When I need to run out of the house these are my go to shoes, but they’re also perfect for something dressier like this.

Photos courtesy Kristin Booker for Giafrese


The Gucci Trousers via @MATCHES_MAN

Part of the reason I like shopping thrift stores is the rush you get when you find that perfect vintage piece. I was both giddy and dumbfounded when I found this pair of pants because they were seemingly tailored for me — literally a perfect fit. With a  slim leg, a dapper crease, a little cuff, and a higher rise than I’m used to, these are the perfect trousers.

Now, I was lucky and paid about $1 for my pants. Hi, thrifty. But for the sake of styling, let’s pretend they’re this pair of flat front trousers from Gucci. Because they’re unbelievably identical in color, cut, and fit.

You can pick yours up at for $524.

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