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The ultimate men's leather shoe guide

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I love a good leather shoe, and I want to own ones that become old friends over time. Finding timeless leather shoes shouldn't have to be a pain, but it's hard to know which brands are genuine and here to stay. I've sorted through and tried out many ...
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Boots and dress shoes - the short list

These are all time great men's leather shoes made by outstanding brands that still care about delivering quality. Pay attention to whether the leather is a traditional calfskin or an oiled leather like Horween Chromexcel, because the care instruction... 

 
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My favorite boot ever (so far). A lifelong boot & daily wearer that you can dress up or down. Hand-lasted in Chicago from Horween Chromexcel (great leather) with a nice color that evolves over time. Wide toe box for comfort. Took me many boots an...
$460 | Trench Boot by Oak Street Bootmakers
 
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Cheapest entry point into a decent quality Oxford ($450+tax), a classic style that covers you with 80% of attire above casual. Classy and comfortable once broken in. This model is still American-made, and the sole is recraftable. Pick between these a...
$450 | Cap-toe oxford dress shoe (Park Avenue) by Allen Edmonds
 
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Carmina is a step above the Allen Edmonds at a slightly higher price point, giving you better leather quality and mirror shine than the Allen Edmonds. The Forest 'last' (aka shoe shape) listed here is their most classic, but you can find different sh...
$630 | Dress cap-toe oxfords by Carmina (Forest 732 last with leather sole)

Expanded shoe selections

If you want to branch out from the short list

 
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Rainbows have been my favorite sandal for 20 years now. Great for everything except wet conditions. Supple leather that forms well to your feet, zero drop with a little arch support means comfortable walking all day. The only item I replace vs repair...
Rainbow Sandals
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A high quality and recraftable boat shoe, similar in style to sperry's but made to last with Horween Chromexcel
Boat Shoe by Oak Street
 
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For something dressier than a boat shoe but not quite a formal loafer, this bit moccasin is one of my new favorites. Horween Chromexcel, comfortable zero drop (no elevation change heel to toe for all-day comfort) recraftable sole like all things Oak ...
Bit Moc(casin) by Oak Street
 
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Handmade in Italy. Beautiful, comfortable, timeless. Small, newer brand but spotted on celebs like Brad Pitt and Jon Hamm.
Leather Milano Loafer by Del Toro
 
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Beautiful buffalo leather for a more distinctive look if you're really into boots. Made in Italy with great attention to detail, they hold an awesome shine and they're comfortable by 3-4 wears. I'd get the Oak Street boot before adding this.
Sloane buffalo chukkas by Untamed Street

Matching leather belts

 
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Chromexcel Dress belts in natural, brown, or black
Oak Street Dress Belts
 
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Casual Chromexcel leather belt to match your boots, comes in natural, brown, or black.
Oak Street casual roller buckle belt
 
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Match color to Allen Edmonds shoes
Allen Edmonds Main Street Dress Belt
 
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Variety of high end belts from Kirby Allison (not yet personally tested)
Luxury Accessories Collection | Leather Dress Belts

Leather shoe care: Horween Chromexcel (oiled leather)

This list is for most of the shoes from Oak Street Bootmakers, which ship with Horween Chromexcel oiled leather. Oiled leather is a different treatment than standard dress shoe leather which requires a different and simpler maintenance approach, invo...

 
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Oak Street has a basic care list and set of instructions, focusing just on buffing and venetian shoe cream for the Horween Chromexcel (oiled leather).
Shoe care instructions and accessories by Oak Street Bootmakers
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Quality horsehair bristle brush by Oak Street Bootmakers
* Horsehair Shoe Brush by Oak Street Bootmakers
 
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Shine cloth / chamois to put the finishing touch on your shoes and buff things out
* Cobbler’s Shine Cloth
 
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3 oz Venetian Shoe Cream for cleaning and conditioning leather. The only product Oak Street recommends with their shoes.
* Venetian Shoe Cream
 
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Saphir cleaning soap, compare to saddle soap. The First step in cleaning your shoe before polishing
Saphir Avel Leather Rejuvenator Cleaning Soap
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A higher-end alternative to Venetian Shoe Cream if you prefer it
Saphir Médaille d'Or Oiled Leather Cream for Chromexcel - 75ml

Leather shoe care for calfskin dress shoes, the expensive list for a nicer shine

For the standard leathers . Some will overlap with the boot care kit (e.g. venetian shoe cream) and some will be unique

 
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Shoe shine fundamentals videos on YouTube, mostly videos by Kirby Allison. Also look at the picture comparing Saphir ($$$) to Lincoln ($$) wax
Shoe Shine YouTube Tutorials
 
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I haven't bought this but Kirby seems to have the best bundle of Saphir essentials to get started with, but if you find something better let me know. You can also piece together what you need from other individual links in this list
Saphir Shoeshine Starter Kit (12 Piece Bundle) via Kirby Allison
 
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Used for reconditioning leathers, this is an extra step you can add after saddle soap if desired. Be careful about using on light leathers as mink oil may darken them
* Saphir Renovateur
 
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Use for applying cream polish and non-mirror shine buffing
* Cotton Chamois Cloth : Shammy Microfiber Cloth
 
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Second step after renovateur or saddle soap is to color and polish with cream shoe polish. Try to get one that's fairly similar in color but don't worry about being exactly right. If you don't want a mirror shine, you can sometimes stop after this st...
* Saphir Médaille d'Or Pommadier Cream Shoe Polish - 75ml
 
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Get a black and a neutral to avoid streaking your lighter shoes with black polish
* Deluxe Shoe Polish Dauber : Shoe Polish Brush & Applicator
 
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Again grab one dark and one neutral to keep your colors separate
* Premium Horsehair Shoe Polishing Brush
 
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Use pate de luxe all over the shoe. Combine with the mirror gloss on the toe and heel where mirror shine is desired (see videos for instructions).
* Saphir Pate de Luxe Wax Shoe Polish 100ml : Saphir Medaille D'OR : Saphir Shoe Polish
 
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use specifically for achieving mirror shine on toe and heel with hard wax polishes
* Wellington High Shine Interlocking Cotton Chamois (Set of 3)
 
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This is an amazing way to get a mirror shine on the toes and heels of your dress shoes. 1 layer pate de luxe, a few layers of mirror shine, then another layer of pate de luxe and buff with the high shine chamois (see videos). Worth the investment
Saphir Médaille d'Or Mirror Gloss Wax Polish - 75 ml
 
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Edge dressing
* Saphir Beaute du Cuir Edge Dressing Pen - 25ml
 
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another source for saphir pommadier polish cream if other links are sold out
Saphir Medaille d'Or Pommadier Cream 75ml
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Leather shoe care for calfskin on a budget

More affordable polishes, less natural ingredients but still decent products

 
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brush, applicator, and chamois (haven't used but seem decent)
Cobbler’s Choice Leather Care Brush Kit Tan
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Generic horsehair brush
Premium Horsehair Shoe Brush with Concaved Handle
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Saddle soap to clean and recondition the leather before applying any polish
Fiebing's Yellow Saddle Soap Leather Cleaner 3.5oz
 
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Can get in any color. If you are buying the nicer shoes above you should probably polish with saphir though
Lincoln Shoe Polish Wax 2-1/8 oz USA
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Meltonian makes a decent cream polish with many colors you can match to your shoes
Meltonian Cream Shoe Polish Oil Based Beeswax
 
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I use generic neutral or black polish, but if you want to exactly color-match shoe polish for your Allen Edmonds this is the source
Cream Polish to match Allen Edmonds colors
 
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On top of polishing your shoes, you also need to keep the lowers of your shoes dressed ("heel dressing"). This is basically painting around the bottom edge (not the main shoe leather) where scuffs accumulate. Test color match before applying.
Heel Dressing from Allen Edmonds