Sartorial Picks

Footwear

Shoes tell people more about you than almost any other element of how you dress and we say this not to create anxiety but because it's genuinely useful information that most men either don't know or know and choose to ignore. The shoes you're wearing are the detail that gets noticed when everything else is working and remembered when something is wrong. We've watched guys undermine genuinely solid outfits with footwear that looked like an afterthought and we've watched simple outfits get elevated significantly by someone who clearly thought carefully about what was on their feet. The good news is that getting footwear right doesn't require a huge investment or an encyclopaedic knowledge of shoe construction. It requires paying attention to a few consistent principles about fit condition and appropriateness that make a significant difference to how everything above the ankle reads as well.

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Ankle Boots

Ankle boots are probably the most versatile footwear a man can own and we say this having tried to argue for various other options over the years before eventually conceding that nothing else quite covers the same range of situations. They work with jeans of almost any cut because the shorter shaft doesn't compete with the trouser. They work with chinos and smarter pants in a way that feels more interesting than a standard dress shoe without being obviously casual. They work with more relaxed outfits without looking like you've overdressed your feet. The key variables are the heel height and the toe shape. A slightly chunky sole with a rounded or almond toe is more wearable day to day than a very flat sole or a pointed toe which is more specific in the outfits it works with. Start with something in dark brown or black and build from there.

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Boat Shoes

Boat shoes are one of those things that work brilliantly when the context is right and look quite wrong when it isn't and the context is essentially summer and relatively casual occasions. They're the shoe version of linen pants in that they're completely correct for certain situations and visibly out of place in others. We love them for exactly the situations they're designed for though. Weekend trips somewhere with water involved. Saturday lunches when the weather has finally decided to behave. Casual summer outfits where trainers feel too sporty and actual leather shoes feel like you're trying too hard. The key with boat shoes is to wear them without socks or with very low no-show socks because visible socks with boat shoes undermines the whole relaxed coastal vibe they're built around. A classic tan leather or navy canvas version covers most situations comfortably.

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Brogues

The brogue is one of those shoes where the decorative element which is the perforated pattern along the edges and seams does something that seems counterintuitive which is that it actually makes the shoe more casual rather than more formal despite looking quite ornate. This makes brogues genuinely versatile in a way that a plain oxford or derby isn't quite. A full brogue or wingtip is casual enough to wear with jeans but smart enough for most office situations. A semi brogue sits comfortably in smarter territory without being as severe as a plain cap toe. We've found dark brown brogues to be one of the hardest working shoes you can own because they go with navy and grey suits beautifully and work equally well with chinos and darker denim for something that looks very put together without a great deal of effort.

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Chelsea Boots

The Chelsea boot is the shoe equivalent of that blazer we keep mentioning in that it works across more situations than almost anything else in your wardrobe and deserves a place in pretty much every man's rotation regardless of what else he typically wears. The elastic sided silhouette is clean and minimal and that minimalism is exactly what makes it so adaptable. It works under suit pants in a way that feels contemporary rather than overly formal. It works with straight jeans in a way that looks deliberate. It works with more casual outfits in a way that adds a bit of sharpness without overdressing the look. Black Chelsea boots in a smooth leather are as close to a universal answer as footwear gets. A tan or brown version gives you something warmer and more casual that works brilliantly for weekends and smart casual situations throughout the year.

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Chukka Boots

The chukka boot sits in a slightly more relaxed territory than a Chelsea or ankle boot and it's that relaxed quality that makes it particularly useful for casual and smart casual dressing. It has two or three eyelets rather than the full lacing of a derby and that detail somehow makes it feel less formal in a way that's hard to explain but easy to see. We love chukkas in suede specifically because the material adds to that casual ease and the way suede wears and ages gives them a character that leather chukkas don't quite replicate. A tan or sand suede chukka with chinos and a simple knit is one of those combinations that looks like you know what you're doing without requiring any particular effort. They also work well with darker casual pants when you want something a bit smarter than trainers but not as formal as a proper boot.

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Derby Shoes

The derby shoe deserves more attention than it typically gets largely because it's been overshadowed by oxfords at the smarter end and loafers at the more casual end without people fully appreciating that it occupies a genuinely useful middle ground. The open lacing system which is what distinguishes a derby from an oxford makes it slightly more casual and also significantly more comfortable for people with wider feet. We've found dark brown or oxblood derby shoes to be one of the best investments in a shoe wardrobe because they go with suits and smart separates beautifully while also working with chinos and smart casual outfits in a way that doesn't feel overdressed. A simple cap toe derby in good quality leather is the version we'd start with because the lack of decoration keeps it versatile across the widest range of situations.

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Desert Boots

Desert boots occupy this brilliant casual territory where they're smart enough to lift a simple outfit but relaxed enough that wearing them never feels like you're trying too hard. The original Clarks Wallabee silhouette that spawned the whole category got something fundamentally right about proportion and ease that's been copied endlessly since. We love them in sand or tan suede for exactly the casual smart combination they do so well. With straight jeans and a simple shirt they look like a considered choice without any of the fuss that more formal footwear brings. With chinos and a knit they hit that weekend smart casual register perfectly. The suede does require a bit of care and a protector spray is worth doing from day one but beyond that they're remarkably low maintenance shoes that work hard across a lot of different situations most men actually find themselves in.

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Leather Boots

A proper pair of leather boots is one of those purchases where doing it right once is significantly better than doing it cheaply several times and the quality difference is obvious enough that it's worth understanding before you buy. Good leather boots have a weight and a substance to them that cheaper alternatives simply don't match and more importantly they improve with wear rather than deteriorating from it. Resoleable boots are worth seeking out specifically because a well made boot with a good upper can last fifteen or twenty years if the sole is replaced when needed. We love a simple leather boot in dark brown or tan for autumn and winter because the warmth of the leather tones works beautifully with the heavier fabrics and richer colours that dominate those seasons. With jeans and a chunky knit and a decent coat this is the footwear that makes the whole outfit feel properly finished.

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Loafers

The loafer is probably the most stylistically interesting shoe in men's wardrobes right now because it's moved convincingly from formal to casual territory over the last several years and now works across a range of situations that would have seemed unlikely not long ago. We've watched loafers go from something you'd wear with a suit to something equally at home with wide leg pants and a minimal tee and that versatility is genuinely impressive. The penny loafer and the horsebit loafer are the two classic styles and both have their specific appeal. We tend to reach for the penny loafer in a dark leather for smarter situations and a suede version in a lighter colour for more casual days. The thing about loafers that took us a while to understand is that they look better with slightly cropped or rolled pants than with a full length that covers the shoe because the silhouette of the loafer deserves to be visible.

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Mule Shoes

The mule shoe for men has had a more interesting trajectory than you might expect given that it started as something associated almost exclusively with very specific style tribes and has ended up being a genuinely useful casual option that a much wider range of men can work into their rotation. The backless slip on silhouette creates a relaxed ease that works particularly well in warmer months. Over a pair of straight cropped pants or shorts with minimal socks or no socks it looks deliberately casual in a way that feels current rather than sloppy. The leather mule in a neutral colour is the most versatile version because it has enough quality and finish to look considered rather than thrown together. Keep everything else in the outfit clean and fairly minimal and the mule does a good job of adding something quietly interesting to a look that might otherwise be fairly unremarkable.

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Oxford Shoes

The oxford is the most formal shoe in everyday men's wardrobes and it gets that status from its closed lacing construction which creates a cleaner and more elegant line than the open lacing of a derby. This formality is the oxford's great strength and its main limitation. It looks impeccable with a suit and genuinely excellent with smart pants and a blazer. It works less naturally with casual outfits where its formality creates a visible mismatch that's hard to ignore. A plain cap toe oxford in black is the shoe for your most formal situations and it's worth having one in good quality leather for exactly those occasions. A slightly more relaxed oxford in dark brown or burgundy with minimal detailing works for smarter business situations and formal casual occasions where you want to look properly dressed without the stiffness of a full formal look.

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Platform Shoes

Platform shoes for men sit in territory that rewards confidence more than most footwear choices and the guys we've seen wearing them well are almost universally the ones who've committed to the look rather than half heartedly including them in an outfit while clearly second guessing the decision. The platform silhouette adds height in an obvious way and that obviousness is actually the point rather than something to minimise. It works best with similarly bold outfit choices. Wide leg pants that show off the platform sole. Clean minimal tops that let the footwear make its statement. The platform loafer and the platform Chelsea boot are the versions we find most wearable for everyday use because they sit within recognisable silhouettes that are just elevated rather than being entirely new shapes that require more confidence to carry off.

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Sandals

Getting sandals right is the footwear challenge that defeats more men than probably any other because the margin between looking relaxed and considered and looking like you've given up on your feet is much narrower than it appears. The main thing we've figured out is that simplicity is almost always the answer. A clean leather sandal with minimal strapping in tan or brown works across more casual summer situations than anything more elaborate. Avoid anything with too much going on strap wise because complexity in a sandal rarely reads as interesting and more often just reads as visual noise. Foot maintenance matters more with sandals than with any other shoe for obvious reasons and this is worth attending to properly rather than hoping for the best. A simple Birkenstock adjacent silhouette or a classic leather flip style in a neutral colour covers most summer casual situations without requiring much thought.

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Shoes

The shoe category taken as a whole is where most men have the most room to improve their overall style with the least effort because shoes are the detail that people unconsciously register more than almost anything else you wear. We've mentioned this elsewhere but it bears repeating because the number of otherwise well dressed men walking around on terrible footwear is genuinely remarkable. What we look for across all shoe categories is quality of leather or material and clean construction without obvious shortcuts. A well made shoe in a simple classic style at a reasonable price point beats an expensive shoe in a trend driven silhouette almost every time because the classic will work for longer and with more of your wardrobe. Getting a proper range of shoes sorted rather than wearing the same trainers for everything is one of the most effective single investments you can make in how you present yourself.

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Slip On Shoes

The slip on shoe in its various forms is one of those practical solutions that works better as a style choice than most people expect. There's a cleanliness to the silhouette that comes from the absence of lacing and that cleanliness works well with simple outfits where you want the footwear to feel effortless rather than considered. We love a clean leather slip on in a driving shoe or penny loafer adjacent style for weekend and casual situations where the ease of just sliding a shoe on without any lacing ceremony is genuinely appealing. Keep the rest of the outfit fairly streamlined and the slip on adds that effortless quality very effectively. The main thing to avoid is anything too casual in construction worn with an outfit that reads as smarter because the mismatch between the relaxed footwear and the more intentional outfit creates a disconnect that undermines both.

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Suede Boots

Suede boots do something that leather boots don't quite manage which is to bring a textural warmth and softness to an outfit that works particularly well in autumn when everything else is getting heavier and richer in fabric and colour too. A suede Chelsea boot in tan or chestnut is one of our favourite pieces for exactly this reason. It adds something interesting to an outfit without being loud about it. The texture catches light differently to leather and creates a subtlety that rewards people who look closely. The care requirements are real and worth taking seriously. Keep a good suede brush and some protector spray around and deal with marks when they happen rather than letting them set. A well maintained suede boot looks genuinely special. A neglected one looks tired quickly and the deterioration is harder to reverse than with leather.

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Trainers

Trainers have been the most significant footwear story in men's style for the last decade or so and the range of situations they're now considered appropriate for has expanded dramatically from where things were even ten years ago. We've watched trainers move convincingly into smart casual territory in a way that would have seemed implausible not long ago. A clean minimal trainer in white or grey or a simple tonal colourway works with chinos and a shirt in most non formal office environments. It works with suit pants in more creative or casual workplace cultures. The key distinction we've found is between trainers that look intentional and trainers that just look like you couldn't be bothered to change shoes. A chunky running shoe with aggressive branding reads very differently to a clean low profile leather or mesh trainer and context determines which one you want.

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Winter Boots

Winter boots are the piece of footwear that British weather makes genuinely necessary rather than optional and yet the number of men we see navigating genuinely awful conditions in shoes that weren't remotely designed for the purpose suggests that actually accepting this necessity is harder than it should be. A proper winter boot solves a specific set of problems. Waterproofing that actually works rather than technically claiming to be water resistant. A sole with grip that handles wet pavements and the occasional bit of ice without incident. Enough warmth that your feet aren't miserable after an hour outside. Style wise we prefer something that looks like an actual boot rather than a technical piece of equipment because it integrates into your wardrobe more naturally and you'll actually wear it rather than leaving it in the hall for emergencies.

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Work Boots

The work boot has made a journey from pure utility into mainstream men's style that feels thoroughly deserved because the fundamental design is really good. The chunky sole and robust construction that were developed for actual physical work environments turn out to look excellent with the right clothes in non work contexts too. A classic leather work boot in tan or brown with straight or slightly relaxed jeans and a heavy knit or flannel shirt creates a very strong autumn and winter casual look that feels current and considered. The weight and substance of a proper work boot grounds an outfit in a way that lighter footwear doesn't and that groundedness works particularly well with heavier fabrics. Buy the best ones you can stretch to because they're genuinely resoleable and a quality work boot with proper care will outlast most other footwear decisions you'll ever make.

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Shoes tell people more about you than almost any other element of how you dress and we say this not to create anxiety but because it’s genuinely useful information that most men either don’t know or know and choose to ignore. The shoes you’re wearing are the detail that gets noticed when everything else is working and remembered when something is wrong. We’ve watched guys undermine genuinely solid outfits with footwear that looked like an afterthought and we’ve watched simple outfits get elevated significantly by someone who clearly thought carefully about what was on their feet. The good news is that getting footwear right doesn’t require a huge investment or an encyclopaedic knowledge of shoe construction. It requires paying attention to a few consistent principles about fit condition and appropriateness that make a significant difference to how everything above the ankle reads as well.

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