I know that for going out or weekend wear that it’s far easier to throw on your trusty sneakers or flip flops (in the warmer months), than it is to find something new. But, just like you’ve been attempting to convince your girlfriend, it’s good to broaden your horizons.
Drivers are classic shoes that are still very much in style now. The low profile is cool and they’re very comfortable.
Topsiders have become hugely popular within the past 16-18 months, and they only look cooler once they’ve been broken in.
Desert boots have been mentioned several times by PG, and that’s because they’re hugely in style right now. These are the originals.
Cool twist on the above.
Though my favorite pair of boots are from Red Wings, I’m not a fan of everything from JCrew’s recent collaboration with them. But these are rugged, without screaming poser.
Banana’s take on the Chelsea boot that come in both brown & black. The dressiest among the bunch.
JCrew’s take on the leather desert boot.
These mid-rise boots are masculine, yet sleek.
Grey is a color that’s often neglected, but when worn correctly they make a very stylish statement.
These may look old-fogeyish but I think they’ll break in well.
Just a simple sleek oxford.
My favorite pair of oxfords on this list.