Shoes paired with different sock styles

Discovery Quiz: What Shoes Should You Wear? For any outfit. Cover your footwear bases from dive bars to interviews

[Feature image by Michelle Tirronen, Studio]

We’ve always found that punchline in Legally Blonde–the supposed statute that only gay guys know shoe brands–a little unjust. In reality, all men can appreciate good footwear.

Shoes have a huge impact on your presentation, in how tied together your look is. And you can bet that if you wear the wrong shoes, a.k.a. combat boots or slippers with a three-piece suit, more than one person is going serve some side eye.

But that’s obvious. How about the less glaring options on an everyday basis?

Tired of wearing the same sneakers day in and out? Unsure of how to dress for a Black Tie event?

Take our expert quiz on what shoes to wear, on any given day:

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See all results for what shoes to wear:


A standard classic when it comes to dress shoes. Oxfords have closed lacing and can be worn with anything from jeans to dress pants.

This sophisticated but laidback footwear provides a slim silhouette that hugs the foot’s contour. Oxfords can be leather or suede and adorned with ornate stitching (or not).

Read more about the Oxford shoe


Similar to Oxfords, Derbys are great smart casual shoes. They have open lacing, making them a bit less formal than other dress shoes.

Derbys were originally intended as sporting and hunting footwear in the 1850s, but now, they pair well with rolled jeans or chinos.

Read more about the Derby shoe


These moccasin-inspired shoes are embraced for their slip-on style. Though casual and comfortable, they still signal an element of style consciousness.

Loafers originated as royal house slippers for England’s King George VI, but by the 1960s, American lawyers and businessmen were wearing them with suits. You can wear loafers with anything from shorts to a casual suit.

Read more about Loafers

Chelsea Boots:

These non-lace ankle boots popularized by the Beatles are a savvy classic.

Fashionable and minimalistic, if you own just one pair of men’s boots, they should probably be Chelseas. Wear them with chinos or dark jeans and a blazer for a night out.

Read more about the Chelsea boot

Desert Boots:

These ankle-length casual boots are made of leather or suede and have fewer eyelets than dress boots.

Desert boots are perfect with rolled pants, relaxed button-downs, and smart casual jackets. They have a slight combat edge to them, but they’re far less heavy-duty than workwear boots.

Read more about the Desert boot

Opera Pumps:

These shoes from the Victorian era are the most formal of all dress shoes. Opera pumps were traditionally worn in the evening for dances, operas, and other social soirees.

If you’re dressing to impress–like, really impress–then go for Opera pumps. This footwear is only suited white or black tie events.

Read more about Opera Pumps

Dress Boots:

Opt for dress boots if you’re wearing a winter suit, or if you just want to demonstrate first-rate style.

The beautiful thing about dress boots is how versatile they are. From cap toes to wingtips to various other stitchings and perforations, you can go smart casual or formal.

Read more about Dress Boots 

Boat Shoes:

Commonly worn by boaters and non-boaters alike for both form and function, boat shoes have become a classic in men’s footwear.

They’re refined and sporty, all in one. Wear boat shoes with anything from shorts to chinos, but make sure you’ve got on no-shoe socks.

Read more about Boat Shoes

Monk Strap Shoes:

These dress shoes are classified as unique, definitely dapper, and a little old-timey.

The Monk strap shoe sits between Oxfords and Derbys in terms of formality. They’re practical and dressy, and a little rarer.

Read more about the Monk Strap Shoe

Converse High Tops:

The original cool, edgy, on-the-go sneaker, Chuck Taylors will never go out of style.

Through wear and tear, through skateparks and trendy lunch meetings, and everything in between, you can incorporate a beloved pair of converse into almost any outfit.

Read more about Converse High Tops

Athletic Sneakers:

Athleisure and luxury sportswear are hot.

Whether you’re wearing chinos, tapered sweats, or even a suit, top off your outfit with an edgy pair of athletic shoes. Look coincidingly streetwise, and business savvy, and like the life of a party.

Read more about Sneaker styles 

Workwear Boots:

Workwear is very much late 2010s. Inspired by streetwear, boots like Timberlands and Doc Martens exude that edgy, modern, semi-grunge style.

Workwear boots are typically heavy-duty, with laces and thick rubber soles. Wear them with distressed denim and long overcoats.

Read more about Workwear Boots


So, what shoes will you go with? Feel free to post photos of your complete look in the comments below

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