The Only 5 Shoes You Need for Work This Season
From formal to casual, these five styles of shoe will see you through the work week in style, whether you’re at the office or working remote.
By: Logan RossDate: 2025-04-07
It used to be that two or three (dependable) pairs of dress shoes would be all the rotation you’d need to take you from Monday to Friday at the office. These days, there’s a good chance you spend more days outside the office than in it.
So, where does that leave the modern five-day footwear rotation? In a place where comfort, self-expression, and variety are more prevalent and acceptable than ever before.
While there’s still a time and place for your best dress shoes, today’s professional should also consider making room for these work-ready shoes in their line-up.
We’ll start with the classics, shall we? If you could only have one style of shoe to wear to work, these would be them. Whether smooth or grained leather, black or brown, these can be worn with everything from a suit to tailored dress pants and even to chinos or jeans, depending on the rest of the outfit.
Oxfords or derbies are a great choice for when you need to look your most formal and/or professional, so most likely for the days you head into the office, are meeting a client, or have an important presentation to give.
Traditionally speaking, oxfords are the more formal of the two, featuring a closed lacing system where the eyelets are attached under the vamp, whereas derbies are slightly more casual due to their open lacing system, featuring eyelets attached above the vamp. These days, they’re essentially comparable in terms of formality, especially in a professional setting.
Taking it down a notch in formality from the lace-ups above are loafers, both in leather and suede variations. While still considered dress shoes, loafers with their slip-on design are decidedly more casual in nature, which means you can wear them on more occasions and with a greater variety of looks.
A suit is the natural home of the loafer, though they look equally at-home worn with tailored trousers, 5-pocket pants, chinos, and jeans as well. Suede loafers take the shoe a notch or two further down the formality scale, though the soft, textured nap of suede can also be worn with tailoring fabrics like flannel wool and tweed.
Whether you’re heading into the office, working remote, or on-the-go, a pair of leather or suede loafers will ensure you look polished and professional (not to mention comfortable) all day long.
It wasn't long ago that the thought of wearing sneakers to work would warrant an audible gasp — but that was before sneakers started looking like these and, crucially, before the Work-From-Home (WFH) era.
The shoes we’re dubbing “sophisticated sneakers” are much sleeker than those based off athletic styles; instead, you can think of these as reverse-engineered dress shoes. A slip-on or understated lace-up design, a smooth leather or suede upper, a low-profile silhouette, and a sole that combines all-day comfort with understated styling.
Although tempting, we wouldn’t recommend wearing these under a suit, however, casual pants like chinos, jeans, and 5-pocket pants work well with sophisticated sneakers. You can pull these off at the office if you've got a more low-key agenda, though they’re more appropriate for comparatively casual off-site work, perhaps at a cafe or shared workspace.
Casual Kicks for On-the-Move
While we’re always full of optimism come springtime, sometimes the weather has different ideas, and on moodier days rain, wind, or even snow (yes, we said it) can get in the way of a good outfit. Not when you’ve got a trusty pair of dress boots to turn to, however.
Think of these like your oxfords or derbies but with a little more heft to them. They’re designed to look as sharp as your dress shoes though are much better equipped for adverse weather. What that results in is a practical blend of elegance and performance that you can wear to the office or while running about town.
Feel free to wear your dress boots with everything from tailoring to denim — you can dress them up or down to suit whatever your day has in store. That said, if you’re wearing a lightweight fabric like linen, a robust pair of dress boots might feel a little overkill.
Undeniably the most casual on the list, mules are a style of shoe that’s slowly crept into the workwear rotation in recent years, and miraculously, without many (or any) raised eyebrows.
The onset of the WFH-era caused a mass casualization of the workplace dress code. Before 2020, how many times had you spent an entire workday in your pajamas? Today, many still spend at least two workdays a week at home, and the ease of mules means garbage runs, dog walks, school drop-offs, and daily chores are that much easier.
The open back and absence of a heel cup makes mules effortless to slide on and off, though the refined, sophisticated upper — often made of luxury materials like suede or calfskin — means they’re much smarter looking than a slipper, slide, or sandal. That said, you can’t really get away with wearing these with anything too formal; steer clear of any tailored clothing, though jeans, joggers, and casual pants are free territory.
Monday to Friday Footwear
