On September 19, 2016, the models at Christopher Kane's London Fashion Week show walked through Tate Britain in Crocs. They were marble-printed rubber, studded with crystals and stones. British Vogue called them the so-called ugly shoes beloved of chefs, hospital workers and surfers, and Kane himself said he loved that they are slightly awkward and might be perceived by some as ugly. That is the whole story of ugly shoes for me: the awkwardness is the point.

 

The clog began as a boat shoe. Crocs debuted at a Fort Lauderdale boat show in 2002, the work of three friends, and the name nods to the shoe's amphibious talent. Balenciaga stacked three sole molds, running, basketball and track, into the Triple S in January 2017. Phoebe Philo showed fur-lined, Birkenstock-style sandals at Celine for spring 2013, and a boutique nicknamed them Furkenstocks. Every one of these shoes works the same way: comfort first, then a wink. I went deeper on a related idea in Pony hair shoes: The Fall Finish That Makes a Clog Strange.

 

Start the walk with the rubber and foam clogs, because they are the easiest to wear on a Tuesday. The Crocs Mega Crush in bone has a chunky lugged sole that makes jeans look deliberate, and the Dylan platform in black is the one I would put under a long slip skirt. Birkenstock's molded Boston in black and the khaki Birki Flow, with its perforated vents, are the lighter, quieter versions. For rain, I would go for the Hunter Elana in pale yellow or the cream Bryce, and the L.L.Bean garden clog if the walk to the door is muddy.

 

October tip: wear any of them with thick wool socks, then check that the heel strap sits snug over the sock and not on top of it.

Clogs earn their place or lose it at the heel, so I would walk the length of a room before committing. A good one stays on without gripping, and a rocker sole should roll you forward rather than tip you back. Dansko built its name on that rocker, and the Professional in oiled black leather is the closed-back version you see on people who stand all day. The Ingrid in honey tan has a heel strap and a lighter look.

 

For softer dressing, the Birkenstock Boston in brown suede has the buckle strap and cork footbed, and it is the one I would wear with cuffed trousers and a chunky cardigan. Frye's Cindy in chocolate leather adds a stacked heel and a buckle, which makes it the clog that reads closest to a boot. Free People's Calli has brass studs on suede with a stacked wooden heel, and the Hudson is a tan leather wedge with a carved wooden heel for anyone who wants height.

 

Sorel's Roam'N in black and in auburn brown is the weatherproof end: studs, a heel strap and a lugged rubber outsole with a cream lug sole on the brown. I would pair it with tights and a short wool skirt in October.

 

Fitting test: run a thumb over the suede and the strap holes before you buy. Suede should feel even and slightly brushed, and the buckle should move smoothly through the strap.

 

What I would skip: a heel you cannot get a thumb under at the back. A clog that slips off at every step will make you hate the whole category.

The Balenciaga Triple S is the cleanest case for how a shoe gets called ugly and then everyone wants it. The ugly sneaker family tree runs through it: molds from a running shoe, a basketball shoe and a track shoe, stacked into a 6.5cm platform. The shoes below are far easier to wear, and they come from the same instinct, bulk on purpose.

 

Start with the New Balance 9060 in brown, which has suede, mesh and a thick layered midsole, and the 1906R in parchment and silver, with metallic overlays and ABZORB cushioning. Both sit well under straight jeans or a long trench. The ASICS GEL-1130 in white and silver and the GEL-NYC 2.0 in silver and cream go the retro-runner route, with layered overlays that catch the light on a gray day.

 

Then the trail end. The Salomon XT-6 GTX in white and silver has the Quicklace system and an aggressive lugged sole, and the HOKA Mafate Speed 2 in lunar rock sits on a thick Vibram outsole. Nike's Air Max Plus Drift has wavy TPU overlays and visible Air, and the adidas Adistar XLG adds gold and pink accents on a chunky layered sole.

 

How to wear them: keep the top half tidy. A tailored coat or a plain knit with wide trousers lets the sneaker do the talking.

 

Buying test: check the lacing, and bend the shoe at the ball. A trail runner should flex where your foot does, not halfway down the arch.

 

What I would skip: stacking a loud sneaker with loud socks and a loud bag. Pick one.

Philo's spring 2013 Celine show gave us the fur-lined sandal, and the Vogue review called those shoes furry, witty and unhinged. I think of that line whenever someone puts a shearling-lined slipper on outside the house. Warm, a little silly, and completely sure of itself.

 

The UGG Tasman II in chestnut suede has braided trim and a shearling lining, and the Disquette is the platform version with a fluffy shearling collar. Both look best with bare ankles and a long coat, or with thick socks and straight jeans. The Vionic Gemma II in cream shearling is the softest of the group, and L.L.Bean's Freeport slide in saddle suede is lined in shearling too, so it works as a house slide that can pop to the mailbox.

 

Then the puffers. Hunter's Madi in white quilted nylon has a toggle cord and a lugged sole, Tommy Hilfiger's Westine does the same in glossy black, and the Merrell Hut Moc 2 in blush pink is a quilted mule with a cream sole. The North Face ThermoBall Traction Mule V in pink has an insulated quilted upper and a rubber traction sole, which is what makes it a real outdoor mule.

 

Test before you commit: check the sole. If you plan to walk the block, look for lugs or rubber traction, not a flat foam slab.

 

What I would skip: a pale shearling slipper on a wet sidewalk. Keep the cream ones for the couch and the train station.

The odd one out here is also the oldest idea. Maison Margiela showed the Tabi in its first collection in 1988, a heeled boot with a split toe, and the soles had been dipped in red paint so the models left split-toed footprints on the white runway. The V&A notes that the tabi sock behind it goes back to the 15th century. Steve Madden's Rapid in brown patent borrows that split toe with a wide hook-and-loop strap, and it is the easiest way to try the shape.

 

The rest of the group is the ballet-sneaker crossover. Puma's Speedcat Ballet Dress-Up in black has a buckled Mary Jane strap on a slim sole, and the Metallic version in jasmine cream and black has cutout straps. Adidas Taekwondo Mei Ballet has ankle ties and a gum sole, while the Tokyo Mary Jane in black and cream adds a hook-and-loop strap and gold metallic trim.

 

For a calmer pair, the Vionic Uptown Mary Jane in desert sand suede, the Kate Spade KS Drift in black with an elastic strap, and the UGG Quill in sand suede with a cut-out strap and treaded sole all look good with a pleated skirt and ribbed socks.

 

Fitting test: the strap should close without pulling the upper across the top of your foot, and the toe box should let your big toe move. A split toe also needs the right sock, so bring a pair.

 

What I would skip: white athletic socks under a split toe. It splits the line of the leg in a way that rarely looks planned.

I would begin where the comfort is and the risk is lowest: a clog, either the Crocs Mega Crush or a suede Boston, worn with thick socks to the first cool morning. If that feels right, add a chunky runner like the New Balance 9060 for weekends and travel.

 

Slippers and Mary Jane sneakers come last, since they are the most personal. Tabi-style split toes are the final step, once you know how you feel about the shape.

 

Kane said he loved Crocs for being slightly awkward. I think the best ones are the ones you stop noticing on your own feet and cannot stop noticing on everyone else's.