Style Guide

Brown and black woven Mary Jane flats on a wooden entry bench beside a folded brown plaid knit cardigan in fall light

What to Wear With Mary Jane Flats in Fall and Winter (6 Outfits)

Mary Jane flats don't have to go away when it gets cold. Here's what to wear with them in fall and winter, with 6 outfits and tips for tights, socks and coats.

Rolled dark denim hem and bare ankles with brown penny loafers on a wooden floor

How to Wear Penny Loafers With Jeans (5 Looks That Work)

Penny loafers with jeans is one of the easiest smart-casual outfits there is, if you get the fit and the hem right. Here's how, with 5 looks.

Black leather sneakers with a worn-in white sole on wet dark concrete with city light reflections

Black Leather Sneakers for Men: What to Wear Them With (5 Outfits)

Black leather sneakers are the low-maintenance alternative to white. Here's what to wear them with, with 5 outfits from all-black to tailored.

Black, camel and silver woven Mary Jane flats laid out with sheer black, cream ribbed and gray ribbed socks on linen

Mary Jane Flats With Socks: How to Pull It Off (5 Looks)

Socks with Mary Jane flats can look polished or playful. Here's how to choose the sock type, color and length, with 5 looks you can copy.

Four pairs of square-toe woven leather Mary Jane mule flats in black, brown, gold and silver laid out on pale stone

Mary Jane Flats: How to Style Them in 2026 (Plus 12 Outfit Ideas)

Mary Jane flats work with almost everything in your closet. Here's how to style them in 2026, with 12 outfit ideas and what to look for in a comfortable pair.

Men's penny loafers in brown, dark brown, tan, black and green suede-look finishes on a walnut floor

Penny Loafers for Men: How to Wear Them in 2026 (10 Outfit Ideas)

Penny loafers are the easiest smart shoe a man can own. Here's what they are, how to wear them with or without socks, and 10 outfits that work in 2026.

Five pairs of men's white leather sneakers with colored star patches and worn-in soles laid out on pale concrete

White Leather Sneakers for Men: How to Wear Them (10 Outfit Ideas)

White leather sneakers go with almost everything a man owns. Here's how to wear them with jeans, chinos, suits, shorts and more, with 10 outfit ideas.