A Kipper Guide
Where To Buy Shoes
Size 6 & Below
While you can wear a suit with sneakers in some instances, situations like a job interview, wedding, or client presentation call for a polished, more traditional appearance. For the average male – roughly 5 ft., 9 in. and around 170 lbs. – finding a dress shoe isn’t a challenge. You stop at the mall, browse online, or, if you’re cash strapped, hunt down an un-scuffed pair at your local consignment shop. In all cases, you expect to find something in your size.
But, what if you’re under 5 ft., 6 in.? Or, you have small feet that feel loose in a size 6? Or, you’re a smaller-sized female with a penchant for actual menswear styles – and those menswear-inspired ones feel too frilly? Unfortunately, you’re stuck: Too small for adult sizes, wanting to avoid anything traditionally feminine, and too large for the kids’ department, you’re in that grey zone where, frankly, nothing fits.
So, what do you do? Suit up and wear all-black Converse high-tops, hoping no one notices? Suck it up and look for a kids’ shoe that’s not-quite-so childish? Or, do you relent, and compromise with a jaunt through the women’s section? The answer is – none of these. We’re here to tell you that, yes, you can find shoes in your size, without compromising your personal style.
Unsure about your foot’s exact measurements? Start with this measuring guide before you shop around.
Our focus here is primarily dress shoes – or whatever you can wear with a suit. On the other hand, if you’re in the grey zone, your shoe collection is – to excuse the pun – fairly small. Maybe two or three pairs, if you’re lucky.
Where do you begin for everyday wear? In this case, any unisex brand is best. Think skate shoes by Vans, low- and high-tops in neutral shades from Converse, Dr. Martens’ boots, and styles from Palladium. For “comfort” shoes, Oofos goes under a size 6, while Clarks hits right at this line.
And, if you see no shame in everyday athleisure, Nike makes men’s sneakers down to a size 4, as does New Balance.
On the department store end, Nordstrom is frequently cited as a place to find smaller-size men’s dress shoes. Of the brands you’ll find below shortly, Grenson and Saint Laurent are available through their online store. Yet, in terms of variety, you can’t beat Zappos. Although their selection of men’s 4 and 4.5 sizes yields mostly casual options, you’ll find an occasional gem: For instance, a pair of Y-3s or a set of Wolverine Heritage boots.
For dress shoes, though, you’ve got to look past the predictable choices. For instance, Stravers – the Amsterdam-based retailer with a world-renowned brick-and-mortar store – prides itself on going to extremes. More specifically, a customer will find more than a smattering of both big-and-tall and small sizes. For the latter, your selection runs typical – think brogues, lace-up ankle boots, and oxfords in brown, tan, and black hues – and less so, with patent leather and blue alligator skin being some of the standouts.
For more technical styles, there’s BootBay.com. Born in east Tennessee in the early ‘80s, it’s another sought-after small-size retailer, with a product selection primarily covering work, hiking, and casual boots. While it’s not directly dress-shoe oriented, we all need a sturdy pair to get through the winter. As such, here you’ll find slip-resistant, moisture-wicking, and cushioned options.
Brands To Buy
Yes, they’ve garnered a reputation as your parents’ (and even grandparents’) shoe store, but this Chicago-originating brand has stuck around for a few reasons. One, you’ll have no trouble getting your basics – oxfords, brogues, chukka boots, and monk strap styles, with the occasional cap or wingtip detail – but its stores continue to stock more fashion-forward fare.
Case in point, at the start of the menswear craze, they partnered with Duckie Brown in 2010 to revamp some of their classic silhouettes, and five years later, they collaborated with George Esquivel on a California-influenced collection. Then, two years ago, they introduced a vintage collection, offering modern takes on their original line.
Richfield Moc Toe Strap Loafer ($100): All-around smooth, except for the slightly angular toe and braided detail, these loafers embody classic simplicity. Pair them with a full suit or chinos and a blazer, and in either instance, their versatile, lightly cushioned design takes you everywhere.
Como Moc Toe Strap Loafer ($110): With a name alluding to Italian construction, this hand-stitched, kidskin loafer is all about the details, from the top strap and burnishing to rich yet not overbearing burgundy undertones.
Menswear has been on a heritage kick, and Grenson fits right in. Although sizing ends at a men’s size 6, their traditional handmade designs make your search worth it. Plus, they’re one brand with a decent women’s selection featuring some unisex-leaning designs. Added to this, their versatility and quality construction mean that whatever you choose – Chelsea and lace-up boots to oxfords, in suede or leather – will last – and last and last. If you’re thinking about building your wardrobe basics, start right here. As a note, U.K. sizing is used for all styles. Reference the brand’s conversion chart to select your size.
Ella Boots (Women’s, $345): Excluding summer’s hotter days, the dress boot delivers the prime combination of style and coverage. Grenson’s Ella cuts out those subtle feminine details, delivering a sturdy wingtip brogue made out of black calfskin leather that’s a sure match for your suit yet is still edgy enough for a pair of jeans.
Dylan Oxford Brogues (Men’s, $330): This traditional hand-painted leather oxford features a tan stain on top of its natural base color for a richer, multi-layered appearance. Best for matching with lighter-colored suits, its wing-tip design uses a slightly longer last than previous versions.
You’ll recognize this British-based brand from Fashion Week presentations. And, much like the clothing we spotted recently, designs go either way – all while still feeling traditional. Whether you’re sporting navy or a multicolored oversized suit, pair it with brogues, loafers, lace-up, or Chelsea boots, in standard leather or nubuck. As a note, the brand uses European sizing for all styles.
Munro Brogues (Women’s, $495): The hybrid dress shoe – leather upper with a sneaker-like sole unit – frequently looks cheap and awkward, but Paul Smith’s Munro hits the sweet spot with vegetable-tanned leather, wingtip details, and a flexible sole with extra padding by the ball.
Gerald Chelsea Boots (Men’s, $340): Now, this is how a Chelsea boot should be: Smooth all around, from the material to the almond toe, with a fit that easily slides on. It’s ready for your suit and also adds that sophisticated rocker touch to denim and patterned pants.
Another American-based brand, Frye hasn’t quite reached heritage status, but their sheer variety – including women’s and men’s styles – definitely impresses us. Pretty much, if you’re looking to build a basic shoe collection from the ground up, you’ll come across oxfords and lace-up boots, as well as a decent, non-statement-making pair of sneakers.
Western Chelsea Boots (Women’s, $358): Not every dress shoe has to be super-traditional, and this music-inspired style – part of a brand collaboration with Cage the Elephant’s Matt Shultz – blends a Chelsea height and Italian leather with cowboy boot elements, like a pitched heel and stitching details.
Grady Jodhpur Boots (Men’s, $398): The jodhpur boot rarely gets enough love from the dress shoe world, we have to admit. Frye’s take definitely leans more toward casual, with its distressed, matte-finished suede and thinner, strap-accented silhouette. It presents a more laid-back version of the Chelsea boot that flows seamlessly from dressier fare to denim.
G.H. Bass & Co.
While you likely associate G.H. Bass & Co. with plaid button-ups and fleece, it’s an American heritage brand in its own right – the maker of the original penny loafer. Although, in a modern setting, the style’s a bit preppy, it’s one of those staples that’s a natural match for your chinos in a pinch. Slip on something smart casual in a range of colors and materials.
Whitney Mirror Metallic Weejuns (Women’s, $120): Traditional construction – a “penny slot,” stitched moc toe, and a slip-on silhouette – meet up with modern statement elements. The result bridges dressy-casual territory with red carpet-worthy style that works with your suit and pretty much the rest of your wardrobe.
Lincoln Lizard Weejuns (Men’s, $120): As another statement shoe, the Lincoln Lizard brings that oomph with lizard stamp burnished crust leather and a chain detail across the top. It’s one of those styles that manages to be current yet classic and formal without feeling overly traditional.
While Hedi Slimane’s since left for Celine, his mod rocker-influenced looks left an impression on this seminal French brand. As such, while critics have been mixed on Slimane’s vision for Celine, they can’t deny he ushered in a new era for Saint Laurent – one of thinner, more androgynous silhouettes that are ready for the boardroom yet have enough punch for an all-nighter in New York. And, as a bonus, you’ll find men’s casual and dress options down to a size 5.
Miles Boots (Men’s and Women’s, $1,195): This unisex-styled boot precisely embodies the post-Slimane Saint Laurent brand, from its thin profile and carefully chosen buckle detail to its clean lines and light hand-distressing.
Laced Army Boots in Kangaroo-Look Leather (Men’s, $1,095): A slightly matte and smooth lace-up upper and a low heel give these boots a light dash of military style. Yet, if you’re going to spend top-dollar on a pair of dress boots, they should also grant you the most mileage, and that’s precisely what this style does, matching everything from intricate printed suits to skinny jeans.
Luxury, high-fashion brands aside, this is your apex. High-quality traditional designs – with the occasional trendy piece, like a military-influenced or two-tone boot – define the “cost per wear” concept. You’ll find all the usual suspects – brogues, oxfords, derbies, monk straps, and a range of boot silhouettes – in versatile shades of tan, brown, and black, complete with details in key places. While this English-based brand originally started as a family business, expansion resulted in brick-and-mortar stores throughout Europe, plus a partnership with Prada. In the U.S., you can find them through Saks, as well as through other luxury retailers like Mr. Porter and Farfetch.
Westerham Oxford (Men’s, $560): It’s quite literally the smoothest oxford you’ll find around, from the blind eyelets to the finished calf leather. Goodyear construction ensures it’ll give you more than a few years’ use, while the cap toe adds an elegant yet neutral finish.
Bessy Buckle Chelsea Boot (Women’s, $814): Masculine and feminine elements fluidly merge in what feels like a true either-or boot. A block heel and buckle strap give it a touch of flair, while the mid-height and finished calf leather elevate it above the typical fashion boot.
Based in San Francisco, Sutro has strived to create a reasonably priced shoe that you’ll wear frequently and that also uses a smaller carbon footprint. To do this, the company works with artisans in Mexico to craft each pair, while the leather, from free-range, U.S.-based cattle, is tanned without chemicals. Instead, natural oils and creams bring out the material’s beauty and highlight its individuality.
Within this approach, craftsmanship remains paramount. Shoes – men’s and women’s styles, with some unisex silhouettes tucked away – are constructed out of full-grain premium leathers, with minimal finishing. For this reason, styles appear simple – lace-up and Chelsea boots, oxfords, and a handful of heeled styles – yet are made to hold up to everyday wear.
Vermont Boots (Unisex, $218): At a glance, can you tell this is a “comfort” shoe? From the leather to the stacked outsole, it deceptively looks like any other dress boot. Yet, this unisex shoe based on Sutro’s best-selling Alder has a few tricks up its sleeve: Mainly, ultra-sturdy Goodyear Welt construction and rubber placed at key pressure points for extra support.
Mendelle Lace-Up Boots (Women’s, $188): Utilitarian details characterize many of Sutro’s styles, and here, the taller height, seven-eyelet front, and smooth, rounded toe give off subtle workwear vibes. Yet, ultra-rugged and clunky, they’re not, and that burnished, straightforward upper makes for a solid, three-season dress boot.
Don’t be put off by the name. We know it seems like a cheesy, fast-footwear ecommerce site, but behind it is handcrafted, meticulous production and some of the finest materials you’ll find around. Designed in Berlin and manufactured in Spain, this brand utilizes Goodyear-welted construction – known for superior strength in work boots – and breathable, French-tanned leathers. Although far from inexpensive, the price justifies itself: For men’s and menswear-styled women’s shoes, the durability and versatile silhouettes are meant to last you years.
N° 5225 Oxfords (Men’s, $385): It’s all in the color. Warm, almost fiery brandy tones – created through a vegetable tanning process – pop without seeming overpowering. A hand finish, applied to soft calf leather, gives it a gradient effect and elegant shine.
N° 275 (Women’s, $465): While these could’ve been an ordinary dress boots, the wing tips and other details reminiscent of a British derby certainly elevate it. Yet, there’s still something rugged about it: Beyond just the Goodyear-welt construction, a taller height, slightly lugged outsole, and seven pairs of eyelets, although decorative, have an old-school work boot vibe.
Here at Kipper, we know a suit’s not complete without the right accessories. If, as a person with smaller-size feet, you’ve come across another high-quality shoe brand, tell us about it on our social channels!