Categories: Shoes

Steve Madden Casual Shoes

S. Madden Juneau Boot – $80 | Draykee Brown Boot – $78 | Wyndham Brown Oxford – $60

Steve Madden’s ability to make a stylish, affordable, and yes, sometimes weird pair of shoes isn’t just limited to the dress oxford realm.  The company also cranks out affordable casual shoes with regularity.  Here’s three of their least expensive and perhaps most desirable pairs up for grabs right now.
.

Juneau Boot – $81.19 for Black | $78.38 for Brown

Don't fear it. Embrace that retro stripe.

That stripe detail is going to scare off a lot of people.  Which is too bad because if you keep the rest of your outfit on the more minimalist side, that could be the one, perfect, stand-out detail that makes your casual look.  Not for anything other than laid back situations, they could become your favorite pair of bang-around-town boots.
.

Draykee Boot – $99.95 for Black | $78.71 for Brown

No one is going to see that stitching anyway..

Is the stitching on the ankle a little goofy?  Undoubtedly.  Are you going to be wearing these boots with shorts?  (Please say no).  If not, who’s going to see it?  Your jeans should cover that part leaving you with a great pair of well shaped casual boots.  They’re thin enough in the toe that you’ll most likely be able to pull off a casual blazer with them.
.

Suede Wyndham Oxford – $71.96 for Black | $59.99 for Brown

As casual (and affordable) as oxfords get.

Men Everywhere are embracing the idea of looking more polished while still dressing down.  Upgrading your casual style doesn’t take much when it comes to shoes.  Oxfords can be comfortable and beat up.  And they look a hell of a lot better on your feet than running shoes when driving around town or working around the house.  These suede oxfords come with an unfortunate pre-wear on the heel and toe (it’s more noticeable on the black pair) but you really can’t beat the price.

Joe

Recent Posts

1 Sale 4 Outfits – Brooks Brothers 25% off + addit. 10% off for members

Stacks on clearance too. 4 style scenarios mined from the BB F&F Sale.

3 hours ago

Style News: Orient is discontinuing the Bambino Automatic OG

A tip of the cap to a real home run of a watch.

4 hours ago

Allen Edmonds Rediscover America Sale 2026 – Top 10 Picks

New releases + timeless icons which rarely go on significant sale. One of their biggest…

2 days ago

Win it: The VAER R1 Oceanracer II Chronograph

USA Assembled. "Speedy" good looks. Sold out, but yours to (possibly) win.

4 days ago

Most Wanted Affordable Style – September 2026

New diver color combos, waxed & quilted jackets, and another alternative to wearing a hoodie.

5 days ago