THE MONK-STRAP DRESS SHOE

Say that 10 times fast (actually, don’t). A monk-strap dress shoe is for special occasions only. Or, if you’re working in a more formal environment, do wear them daily.

Wear it with:

• Your 9-5 standard suit in charcoal grey or navy—make sure your belt matches your shoes
• Dark wash jeans & a checkered button down 
• Get your geek on. Show them off in cuffed chinos, colorful socks a shawl collar sweater

THE BROGUE

Go brogue. A nod to our friends across the pond, these classic shoes are easily recognizable by their cap toe and decorative perforations. They tend to have a dressier feel, so wear them accordingly.

Wear it with:

• Channel the ‘30s and ‘40s and pair with a double-breasted grey suit
• Cuff your jeans, roll up your white T-shirt sleeves and wear with an open flannel shirt
• Wear with chinos and a polo to work

THE CHUKKA BOOT

Also knows as the desert boot, this summer to fall staple is our Editor’s standout shoe of the moment. Why? Chukkas are a great staple and they’re versatile enough to wear with jeans or chinos. Enough said.

Wear it with:

• Your casual Friday jeans & a polo
• A sweatshirt & chinos
• Selvedge denim, a casual henley & a rain jacket

The Sneaker

Allow us to reintroduce the sneaker. It’s not for the gym—it’s for everyday living and they pretty much sell themselves. Buy a pair in black, one in white and one in tan. Then, wear them all year long.

Wear it with:

• Shorts &  a short-sleeve Hawaiian shirt—then, book yourself a tropical vacation
• Jeans & a jersey (for Saturdays only!)
• Jeans & a tee