It can be frustrating when you buy a slick pair of new shoes only to find that they don’t go with any of the outfits in your wardrobe. And with so many styles of shoes, sneakers, and boots out there to choose from, putting together a good clothing combination can sometimes get tricky. That’s especially true if you’re trying to nail a smart casual get-up for a special occasion or elevate your day-to-day streetwear game.
In this article, you’ll find a comprehensive guide on how to pair men’s shoes, sneakers, and boots with just about every type of outfit on the planet. Gone are the days when you would have to turn up to a wedding in a drab outfit to match your brogues or attend the office party in a pair of loafers because it seems like a safe choice. With the tips found here, you’ll soon be rocking up to every occasion as the best-dressed man in the room and looking great in your downtime too. The key to all of this, of course, is to start with your shoes!
DRESS SHOES
What outfits to pair with
Ah, the trusty dress shoe. A lifelong companion to every well-dressed man since they were created a good five centuries ago. From Oxfords and brogues to Derbys and Monks, dress shoes pair well with just about every kind of formal outfit out there. Whether it’s a three-piece suit or office attire, the perfect pair of dress shoes can form the pièce de resistance to many a smart outfit.
Not only this, but dress shoes also function brilliantly as part of a smart-casual outfit. Throw a pair of sleek leather or suede dress shoes on with a blazer and colour-matched chinos, and you can look right at home at your after-work occasion or informal business meeting. For summer, combine a linen shirt and cotton trousers with a pair of loafers for a relaxed beachside effect. Meanwhile, in the autumn, you can pair a long coat and a woollen scarf with fitted jeans and leather brogues for a cozy, city-roamer style.
What outfits NOT to pair with
There are certain limits to what the humble dress shoe can achieve. While some experimental streetwear getups do include them, you’re probably best off leaving this look to the pros and trendsetters, lest you end up looking like a waiter on his way home from a long shift. The same goes for casual outfits. Smart casual is one thing, but if you’re dressing down on the whole, then a pair of dress shoes can really mess with your overall style and leave you stuck somewhere in no man’s land between formal and casual.
Socks or no socks?
As a general rule, you should always wear socks with dress shoes. And if you are going to do so, then they should absolutely be dress socks and not sports socks or other thick socks that might overwhelm the cuff of your shoe. If your socks are on show under ankle-cut trousers, try to go for a similar colour to your shoes but a different shade, e.g. grey socks with black shoes, just for a little bit of added contrast.
Don’t let your socks bunch up, and don’t show skin, with one exception. If you’re going for a breezy summer look, then a pair of no-show ankle socks beneath loafers or boat shoes can make for a really fantastic combination, especially when paired with a linen suit or smart linen trousers.
What colour combinations to use
A rule you’ll see repeated throughout this article, and across many others, is that you should always match your dress shoes with your belt when pairing colours. Your ultimate aim here is to match all of your accents across your outfit, with two accent shades at the most, generally speaking. So, for example, if you’re wearing a navy suit with chestnut buttons, you’ll want to pair it with burgundy brogues and a burgundy belt. For a bit of variation, you might then go for a pale blue shirt to match the navy while acting as an accent in its own right, or a stark white shirt to offset both colours and allow both the brown shades and the blue shades to stand out on their own.
Black shoes are a must-have in this regard, as they go with so many outfits and lots of darker shades of trousers and suits, especially black suits, dark navy suits, and grey suits. For lighter shades, chocolate, burgundy, and tan dress shoes can pair very nicely, and chocolate and burgundy in particular work well with blue outfits too. For a statement shoe, brogues and detailed Derbys add a nice bit of flair, whereas if you’re wearing plaid, dogtooth, or tweed, a plain shoe might be a better choice as not to overwhelm your already busy outfit.
Pair with jeans?
Wearing dress shoes with jeans is always a tricky one. In some cases, it looks fine, say if you’re going for a smart-casual look with a pair of slim or low-cut jeans. On the other hand, if you’re wearing distressed, baggy, or ‘dad’ fit jeans, then it’s often not a good idea to pair these with dress shoes. Jeans with too much slack can look silly with shiny dress shoes poking out from underneath them, and the same goes for super-skinny jeans. Slim jeans or slimline straight-leg jeans act as a good middle ground here, either with their cuffs over your laces or rolled up neatly just above the cut of your shoes for a nice cut-off effect.
SNEAKERS
What outfits to pair with
If you’re wondering how men pair sneakers with outfits, then you’ve come to the right place. Sneakers are generally a little easier to work with than dress shoes because they’re super versatile within all kinds of outfits. For a casual outfit, they’re your bread and butter – an all-white or all-black pair will match with practically anything in your wardrobe. If you’re going for citybound streetwear, sneakers can be a great statement piece to throw in or a nice addition to your overall colour profile, whether they’re a chunky pair adding some depth or something more tapered building on a sleek, slim outfit.
Turn the dial up ever so slightly, and you enter the wonderful world of Normcore. Many attribute this realm of style to the 90s and its once-icons, namely Jerry Seinfeld and his vast collection of sneakers. In actual fact, Normcore describes a great many well-put-together outfits that incorporate sneakers into their look. Whether it’s a button-down cord shirt or a plain white tee and dad jeans, sneakers can help dress down or flair up an otherwise old-school or boring outfit and turn it into something trendy. Sports sneakers are especially great for this, so think Nike, Adidas, Asics, and the like.
Last but not least, there’s the wonderful world of formal outfits with sneakers thrown in as a statement piece. Take a brilliant blue suit with a pair of dazzling white Chuck Taylors or a striking long coat and a broad-brimmed hat with some Nike Air Force down below. Whether you’re looking to bring a casual feel to a family wedding in the summer, or you’re stepping foot-first into the tailored streetwear game, this can be a really fun area to experiment in with sneakers.
What outfits NOT to pair with
While sneakers are some of the most versatile types of shoes on the planet, there is one place they’re a true no-go, and that’s at black-tie or highly formal events. There’s a difference between Daniel Craig wearing white Converse at a movie premiere and James Bond arriving at a funeral in a pair of New Balance, so if in doubt, go without, and find something a little more formal.
Socks or no socks?
Sneakers and ankle socks go together like, well, sneakers and ankle socks! Pretty much every outfit that includes sneakers can be improved by swapping out full-length crew socks for short ankle socks, especially during spring and summer. Meanwhile, in the winter, a nice pair of ribbed sports socks or colour-matching branded socks that Adidas and Nike sell can pair with their respective shoes brilliantly.
For more formal outfits, smart casual slip-on sneakers look great with no-show ankle socks. In general, the only thing you want to avoid is wearing sock colours that overwhelm your treads, especially if you’re wearing multicolour statement sneakers. Otherwise, a contrasting sock can look great with sneakers if worked into your outfit’s overall colour profile.
What colour combinations to use
The key with sneakers is to make up your mind what role they will be playing in the colour profile of your outfit. As noted, colourful statement sneakers are a great addition to an otherwise subtle outfit, as they’ll draw the eye brilliantly beneath a pair of stonewashed jeans or when matched with a simple block-colour sweater and dark chinos.
Your other option is to coordinate your sneakers with matching accents across your outfit. A classic example is the Nike Cortez sneaker in white, with its red swoosh and blue stripe across the sole. To coordinate with this, you might wear blue jeans, a white tee, and a red jacket, bringing together all of the colours of your sneaker while allowing them to stand out as a statement piece that includes a little everything from your outfit. This works with all sneaker colorways; take one or two colours from the sneaker, and match it with accents or individual items from your outfit without using too much of any one colour.
Pair with jeans?
Sneakers go very well with all varieties of jeans, from baggy boot-cut classics to straight-leg dad jeans to spray-on super tight skinny jeans. Don’t settle just for jeans, however. A pair of vintage corduroy trousers or classic Normcore slacks can look great when matched with the right sneakers, and you can even dress down a pair of comfortable suit pants with some sports sneakers for a smart casual look that’s more casual than smart.
BOOTS
What outfits to pair with
Boots are another incredibly versatile item of footwear when it comes to outfitting combinations. This is thanks to the sheer array of boot types on offer, and so here, you’ll find some tips that focus on a few key varieties.
The first and foremost thing a good boot lends itself to is a rugged, casual look. Think a layered look with Carhartt workwear or repurposed workmen’s trousers and a pair of sturdy work boots to finish the job. Add softer tones with comfortable cotton sweaters or billowy t-shirts to create a look that’s both strong and gentle.
Meanwhile, if you’re getting dressed up for an occasion, a more formal pair of boots can make for a great smart casual pick. Chukka boots are an excellent choice, especially in suede designs, as they pair nicely with rolled-up jeans or straight-leg trousers for a jaunty look that’s still somewhat subtle. Desert boots are similar and can lean into more formal looks well, while Chelsea boots are a fantastic all-rounder for both ends of the smart-casual spectrum.
Some lace-up boots are smart enough to pass for semi-formal occasions, and they’re a good pick for outdoor weddings or events where some walking between venues is required. For pure streetwear potential, meanwhile, combat boots are a fantastic choice, combining nicely with trench coats or repurposed workwear for a powerful, masculine style. And then there are the classic Doc Martens – a great choice for all of these scenarios and more.
What outfits NOT to pair with
The only thing you need to consider with a boot is that not every pair of boots will fit every occasion. Rugged boots should never be worn to more formal occasions, just as Chelsea boots might look out of place under a laid-back hoody and baggy jeans. Likewise, pairing boots with shorts should generally be avoided unless you’ve got a very specific summertime outfit in mind.
Socks or no socks?
Boots are usually made from hard-wearing materials like leather and rubber, so it can be unwise to go sockless while wearing them. Materials like these, especially when not yet worn-in, can rub against your ankles, heels, and toes, so wearing socks is vital when rocking a pair of boots. Of course, if you’re wearing boots with a low-ankle cut, then you’d be wise to pick out a nice, subtle colour of socks to go with them, like lilac-pink dress socks with chocolate suede desert boots or high-contrast white socks to go with black Doc Martens.
What colour combinations to use
As many boots are made from leather or suede, you can generally follow the same rules in terms of colour combinations as you would with leather dress shoes. This means matching accent colours with your boots or using them as a standalone statement piece. As boots are often larger than dress shoes, they make good standalone picks that can balance an otherwise one-shade colour profile, like combining soft brown chukka boots with blue jeans and a blue blazer.
Pair with jeans?
Boots of all kinds can easily be paired with jeans, but take care around the cuff area and try not to mismatch colours. Brown boots work great with blue jeans, as do many black boots, but certain shades just won’t look right to the eye. If you’re wearing thick boots, it’s best to tuck your jeans in, whereas for slim boots or ankle-cut boots, you can let them sit over the boot itself or roll your hems up a little for a more casual look.
CASUAL SHOES
What outfits to pair with
When it comes to casual shoes like moccasins, boat shoes, city brogues, and tennis shoes, the sky is the limit in terms of outfit combinations. Even when just focusing on casual applications, there’s still a lot that you can do. For example, a pair of moccasins can be a great option for smart casual outfits. As comfortable as a sneaker and as smart as some casual dress shoes, they’re a great pick for all manner of travel and relaxation outfits.
Espadrilles are another type of casual shoe that makes for great beachwear and is perfect for short city strolls and lounging around the house. Casual Derby shoes, meanwhile, are a classy, understated pick for weekend hangouts and shopping trips, and they look just as good with rolled-up trousers in the summer as they do with long coats and bomber jackets in the winter. In terms of streetwear, canvas shoes like Vans and Chuck Taylors are both excellent choices, while tennis shoe staples like Adidas’ Stan Smith’s go with all manner of outfits thanks to their wide range of men’s shoe colour combinations.
What outfits NOT to pair with
When it comes to casual shoes, if you’re going to be formal, be formal, and if you’re going to be casual, be casual. While combining suits with sneakers is occasionally fun, wearing subtle, casual shoes with an otherwise dressed-up or snazzy outfit can turn even the best fit into a bit of a damp squib. Most casual shoes should only be worn in casual settings, as otherwise, the relaxed aura they give off can end up feeling out of place.
Socks or no socks?
When it comes to casual shoes, it really is up to you whether you wear socks or not. Low-cut casual shoes like Vans look great with regular or no-show ankle socks, whereas casual Derbys and brogues are some of the few shoes that pair well with patterned socks, owing to the contrast they provide with their sleek and refined designs. Think about the style of the shoe and pick socks to match; smarter casual shoes like Doc Marten’s Coronados look good with dress socks, whereas sportier tennis shoes match well with ribbed sports socks.
What colour combinations to use
If you’re using casual shoes to curate a laid-back outfit, go for subtle colour combinations like white shoes with lilac socks or brown casual brogues with dark grey socks. Try to avoid pairing light brown with black, as this always creates something of a drab effect, and feel free to experiment a little more than usual with your overall outfit colour profile. Most casual shoes are single-tone or two-tone in their colorways, giving you more freedom to play with the rest of your outfit.
Pair with jeans?
Again, with so much variation going on, many casual shoes pair brilliantly with jeans but do still take some care. If your casual shoes are based on a dress shoe style, then you need to follow the same rules as would normally apply – that means if they’re smart, avoid jeans with too much slack, and try to match your accents up as best you can. When it comes to canvas shoes and tennis shoes, meanwhile, you can wear jeans of pretty much any style and still look great.
