‘Tis the season. The going-out season, that is. With the number of holiday parties, work events, and weekend hangs with friends and family on the horizon there is a chance you will have a multitude of events to attend, each with a different dress code. When it comes to shoes, the options are plentiful. Maybe a little too plentiful?
So to make sure you’re sporting the right men’s shoes to the right events, here is some inspiration to help choose your footwear that bit easier.
1. Ankle Boots
Ankle boots can be casual or dressy, depending on the material and design. A two-toned ankle boot can be the perfect finishing accessory to black jeans and a casual sweater, giving you the appearance of being a smart casual dresser, ready to go from work straight to drinks with friends without having to change first.
Feeling a little fancier? Try a pair of black Italian leather ankle boots with cuffed black tailored pants and a collared shirt. If you have a sweater vest to add, that is up to you. However, if the event has a Christmas vibe, choosing a sweater with embroidered reindeer and Santa is always a win-win situation for everyone involved.
2. Boat Shoes
Boat shoes are definitely a more casual vibe, so do not wear these with a three-piece suit or to an event labeled as “formal,” but you can definitely throw on your darkest indigo jeans, a white button-up, and a blazer for your holiday work lunch or on a Saturday for hanging out with your lady friend. If shorts are more your thing, boat shoes are a great way to spruce up your salmon shorts and light sweater.
3. Brogue
When the occasion calls for a more formal look or you just want to make everyone else look bad, you can’t go wrong with a classic brogue shoe. Pull out all the stops with an Italian bespoke pair and wear them with your best suit.
If you want to tone down your look a bit, don’t wear a full suit but rather the pants and vest, sans sportcoat. Try a pair of brogue shoes in oxblood or walnut and a pair of socks with a festive pattern, just for fun. Even if you’re not easy-going, your socks will trick people into thinking that you are.
4. Chukka
Chukka boots can be as versatile as a standard ankle boot. For a higher-end fashion version, try a pair that is light-burnished and hand-welted worn with your best tailored pants. A suede chocolate brown pair looks nice with jeans and a button up or a sweater. Throw on a navy or camel wool coat to pull the look together as you navigate the streets to your next event.
5. Converse
Nothing says you know how to do smart casual like suiting worn with sneakers. Tailored pants and sneakers are one of my personal favorite wardrobe options for literally any occasion, whether it’s a casual Tuesday at the office or Christmas dinner with friends.
Trying to keep your whole look casual? Easy peasy. If you’re sticking with the current trends then oversized pleated khaki trousers and a polo shirt from 1996 worn with your favorite Chuck Taylor All-Stars is the way to go. And if it’s on the chilly side, a Champion sweatshirt should do the trick while keeping your style consistent.
6. Derby
Derbys, brogues, and Oxfords oh my! Although similar in style, each shoe has its subtle differences. That being said, dressing the rest of your body can be similar as well. A tailored pant, button up, tucked-in sweater, and a tie are never wrong. Add a hat for extra hipster appeal and hit the streets with confidence.
7. High Top
Not all going-out outfits need to be dressy. Skinny black jeans, a sweatshirt, and a pair of Nike Blazer Mid 77’s will have you dressed right for a night out with your friends from high school during that fateful week in between Christmas and New Year when no one knows what day it is, what time it is, or where they are. Best. Week. Ever!
8. Leather Boot
If you’re looking to up your style game, leather boots always do the trick. Ease in with a pair of leather chukkas or ankle boots worn with your favorite denim, a t-shirt, and plaid flannel. Are your leather boots black? They can still be worn with denim, obviously, but black can dress up those tailored dark gray ankle pants and have you stepping out with confidence.
9. Leather Sneakers
Sure, they can come in the usual suspects of leather colors – brown, black, and oxblood – but I bet you already own a pair of leather sneakers in white; Nike Air Force 1’s, Adidas Gazelles, any style of Veja… However, if leather is not necessarily your thing, whether you’re vegan or for other reasons, you still have so many options for leather-like kicks. adidas has an entire vegan line of their most popular styles.
10. Loafers
Loafers. The shoe that feels casual in nature but actually looks quite dapper. Especially when made in velvet or leather. Loafers with denim is not a favorite look amongst the fashion-minded, but pairing them with dark or patterned tailored pants and a sportcoat minus the tie can still give your outfit a comfy, casual feel while simultaneously appearing lavish and elegant.
11. Low Top
Whether you choose to rock a solid white low top sneaker, because frankly, they look good with virtually everything, or the latest collab from Off-White x Nike with joggers or jeans, every male on the planet needs several pairs of low top sneakers for multiple occasions. If you are more of a sock guy, a pair of clean, white low top sneakers with cuffed ankle pants is the perfect way to show them off.
12. Monk Strap Shoes
Nothing says “finely dressed gentleman” like monk strap shoes. These are not recommended to be worn with jeans. No, no. Instead, these go best with your more formal and semi-formal occasions and looks. If you really want to step your game up, having a bespoke pair made from patina leather will have people giving you double takes.
Personally, if I see someone in a pair of monk strap shoes, they get an automatic Chef’s Kiss from me as I pass them by on the street. I’m sure they have no idea why I respond in this way or to what I’m referring to, but now they do.
13. Oxford
Oxfords, like their similar derby and brogue cousins, come in a multitude of leathers, fabrics, tones, and colorways. They are versatile and can take an every day, drab look and kick it up a few notches.
14. White Shoes
High tops, low tops, boots, chukkas, suede, leather, vegan leather, canvas… you cannot go wrong with a white shoe. Unless you’re going out to a backyard after a hard rain or snowfall. Then I would reconsider. Wearing plaid fitted trousers and a tucked-in t-shirt? White low-tops are the perfect compliment.
Decided on khakis and a navy v-neck sweater? Roll up your pants and throw on some white high-tops. White matches with just about everything, so when in doubt, you now know what to do. You’re welcome.
Conclusion
Wearing the right pair of shoes can really take a look from “so-so” to “oh, yes he did!” Sometimes, a certain look calls for a specific style, but usually, you can mix and match and be casual one day and fancy af the next day. As long as you have options, you are good to go. Go forth and enjoy your holiday season without worrying about what is on your feet. You made the correct decision, so trust your instinct.
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