How to Pick the Right Shoes for Every Outfit

The RIght Shoes 2.16.16

There’s a place and time for everything. This saying couldn’t be more true when it comes to the way you dress. We can talk about this from your head to toes, but for right now let’s start off with shoes.

I had someone ask me the other day, “What shoes should I wear with this outfit?”. We can go on for hours talking about what shoes to wear with a specific outfit. But I thought a better way to answer my friend’s question would be to explain which style of shoes are best to wear for different occasions.

You don’t need a collection of shoes for every occasion. There isn’t a rule against wearing sandals in the rain but I would definitely recommend to wear some killer rain boots to keep your feet dry and in style.

Here are my top shoes you can wear with several outfits for any occasion. I don’t like to think of these as ‘rules’, but more of a guide. Keep in mind that what you wear is an expression of yourself, so if you like it, wear it.

Work Shoe

Cap Toe Shoe: If you work in a corporate setting, your go-to shoe should be a pair of black cap toe shoes. It’s a standard, classic shoe that every corporate man should own and it is extremely versatile. It can be worn with a grey, black and even blue suit (for the more experienced dresser) or with just slacks and a button-up shirt. It’s also a good formal shoe to wear to a wedding or for suiting up for a night out on the town. This shoe is meant for a dressier look.

Hugo Boss Oxford with Cap Toe

Hugo Boss Metost Oxford

Casual Work Shoe

Wingtip Oxford Shoe: For those of you with a more relaxed dress code at the office, this shoe is for you. Nowadays, more office jobs have a laid back dress code but that doesn’t excuse you from looking your best. Wingtip oxford shoes go great with a nice pair of dark jeans or chinos. Make sure the shoes are made of a softer leather, it’s meant for a casual look. You’ll notice some wingtip shoes are made of a stiffer leather. Those are meant for dressier attire.

Cole Haan Williams Wingtip II Oxford

Cole Haan Williams Wingtip II Oxford

Date Night

Double Monk Strap Shoe: This is your time to shine! Some guys find dressing up for work a chore (which it shouldn’t be!), but whether you enjoy dressing up or not, everyone wants to look good when they go out. A double monk strap shoe is THE SHOE to help you make an impression! How often do you see a guy wearing these shoes? Not often. Which is why these are the perfect shoe for a special night out. Wear this shoe with the sharpest suit or the best pair of jeans you own and pair with a blazer and a tucked in buttoned-up shirt.

Magnanni ‘Miro’ Double Monk Strap Shoe

Magnanni Miro' Double Monk Strap

Casual Date Night

Loafers: It’s a casual night out but you’re still ‘going out’, so leave the sneakers at home. You can still wear something comfortable and have a stylish effortless look in loafers. Throw on some jeans with your loafers and a nice, plain v-neck t-shirt or sweater and out you go!

 Style Tip: Go with a sockless look by wearing no-show socks.

Cole Haan Ascot II Bit Loafer

Cole Haan Ascot II Bit Loafer

Utility Boot: Another good option for a casual night out is a solid pair of combat boots. These boots will give you a rugged look. Cuff those jeans when you wear combat boots.

Kenneth Cole Reaction Steer the Wheel Boots

Kenneth COle Boot

Weekend Casual Shoe

Desert Boot: Whether you’re heading out for brunch on Sunday morning or meeting with friends for coffee, you want to look and feel casual. Desert boots are the most comfortable pair of shoes that I own. Not only are they comfortable but the older and more worn that these shoes get, the better they look. Wear these shoes with whatever outfit you would wear if you were wearing sneakers, such as khakis or jeans. Except, you’ll look way more stylish.

Clark’s Original Desert Boot

Clark’s Original Desert Boot

Lounging Around

Jack Purcell Converse: This is the ultimate casual shoe. This is an iconic shoe that has been around since the 1930s. And there’s a reason for that. These sneakers are perfect to wear for a day at the park or hanging out at home with buddies watching the game. Wear your most comfortable t-shirt, show some ankle by cuffing your khaki pants and turn on the chill mode. Don’t forget those no-show socks again!

Jack Purcell Converse

Jack Purcell Converese

I hope you found these tips helpful! I’d love to hear from you guys. For more tips, topics or questions, shoot me an email or connect with me on social media!

 Until Next Time, Gents!

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