The Dappered Gift Guide for The Shoe Guy

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About the Author: Adam Terry is a thirtysomething salesman in the heating and manufacturing industry. He enjoys bourbon, boots, sneakers, denim, and working on his ~~dad bod~~ father figure.

Tis the season to be bombarded by gift guides. But instead of doing a highly generalized, throw-everything-against-the-digital-wall mega post, we’ll be breaking it up by category and dropping multiple guides in the coming days. Gifts for the guy who likes watches. Or the rugged type. Or the guy who’s really into shoes. Etc. We’ll cover all those, and hopefully a few more over the next week or so.

NOTE ON BUYING SIZED ITEMS: Make sure you pay attention to the return/exchange policies. Lots of retailers are doing extended return windows this time of year, but far from all are extending that courtesy. The last thing you want is to stick your giftee with something that doesn’t fit and can’t be returned.

We’re gonna break this particular guide into two parts. First, the shoes (or boots). And then we’ll finish it off with socks, shoe-care, and other related footwear accessories the true shoe-hound might love.

Boots, Dress Shoes, Sneakers, etc.

Dress Boots (Smart Casual)

‘Tis the season.. for boots! If your giftee regularly wears upscale “smart casual” clothes like suits, sport coats, pressed chinos, etc., then consider gifting them a high quality pair of boots that can pair well with a wide range of nicer outfits. Nice boots with durable leathers and solid Goodyear welted or stitchdown construction don’t come cheap, so invest a bit more upfront so that these can be worn for years.

Heritage/Americana Boots (Casual)

If your giftee is more of the flannel and jeans type of guy, consider upgrading their pair of entry level “workwear” style boots with something nicer that can elevate their day to day outfits. Again, you’re looking for something that’s made with good leathers and features Goodyear welted or stitchdown construction so that the boots can be worn hard for years before needing a refresh.

Chelsea Boots (Smart casual)

Skimp: J. Crew Kenton Chelsea Boots in “Color 8” – $298 (shown above = the 2021 version. 2022 could be slightly different leather. Review of 2021 can be found here.)
Spend: Grant Stone Chelsea Boots – $370
Splurge: R.M. Williams Classic Craftsman Leather Chelsea Boots – $530

Chelsea boots typically fill the niche between the more formal dress boots and the more casual chukkas. These elegant slip-on boots are designed to pair well with those “smart casual” outfits with sport coats, button-down collar shirts, and neat chinos, but they can also be dressed down with a crisp shirt and jeans for a casual date night style. Look for something with a simple leather or suede upper and a slim leather or rubber sole that’s been welted or stitched on.

Chelsea Boots (Casual)

Skimp: Blundstone Original 500 Chelsea Boots – $215
Spend: Huckberry Rhodes Jackson Chelsea Boots w/ Lug Sole – $224 ($298) full review coming soon!
Splurge: R.M. Williams Gardener Whole-Cut Chelsea Boots – $530

Casual Chelsea boots are super popular right now as they’re easy to wear with just about anything. You’ll want to choose a slightly chunkier style or something with texture – suede uppers or lugged soles – as to differentiate these from the dressier options already mentioned. As with everything else so far, invest a bit more now so that these boots last for years to come.

Chukka Boots (Smart casual)

Personally, I love a good pair of chukka boots as they pair well with dressed down business casual styles. Many of us are working in a hybrid office role these days; you’re in the office a few days a week, but you can also work remotely a few days to help cut down on traffic and office expenditures. This means our clothing needs to be more versatile than ever, so smart chukka boots pair well with a wide range of styles. I like to wear mine with a simple knit polo and jeans.

Chukka Boots (Casual)

For those guys who prefer a more casual weekender vibe, desert boots are the quintessential casual chukka boots. These will feature paired back uppers – usually unlined leather or suede – stitched down to a crepe or manmade rubber outsole. Two sets of eyelets and simple lacing help keep these boots grounded to the casual realm. These are best paired with basic outfits like flannels, henleys, or crisp tees with five-pocket pants, stretch chinos, and jeans. Easy!

Oxfords, Derbies, Bluchers, etc. (Smart casual)

Some guys don’t like to wear boots to work, and while we might think they’re a bit weird, that’s alright. To each their own! If your giftee prefers more formal Oxfords or “smart casual” derbies and bluchers with their outfits, consider gifting them a well-made pair like these below (or a gift card towards a pair). A high quality pair of dress-focused shoes will have more elegant leather uppers, soft leather linings, leather or rubber outsoles, and Blake or Goodyear welted stitching.

Loafers (Smart Casual)

Loafers have been going through a resurgence in popularity over the past few years. They’ve always been a staple for the Southern gentleman, dressed to impress during Spring and Summer, but we’re seeing them catch on with other styles and subcultures, too. I’m a fan of the American penny loafers as they pair well with a wide variety of “smart casual” office wear.

Smart Sneakers (Smart Casual)

Skimp: Beckett Simonon Morgen Trainers – $159 (Made to Order)
Spend: Rothy’s RS01 Sneakers – $170 review here
Splurge: Rancourt Bennett Court Sneakers – $295 (Made to Order)

There are a million different sneakers out there to choose from, but if we’re looking to surprise that special someone, let’s make them feel special with a gift-wrapped box of nicer sneakers designed to pair with those “smart casual” Spring and Summer outfits. You’re looking for higher quality materials and understated or conservative colorways to pair with just about everything.

Athletic Sneakers (Casual)

If you’re shopping for the marathon runner, trail master, or gym rat in your life, a good pair of supportive and comfortable athletic sneakers can help the recipient go that extra mile. These selections will be highly subjective as fit and the performance engineering behind each sneaker can vary. While I personally like the pairs picked, don’t be afraid to get them a gift card towards a new pair or link up with a store like Fleet Feet near you where they can size ‘em up right.

Boat Mocs/Slippers (Casual)

While most of us are now dealing with the colder weather, comfort is always a personal thing. For some of us that live down South, we still like to wear our boat mocs and penny loafers regardless of the weather outside. I’ve spent more time in my home office this year than ever before and I’ve recently discovered that it gets cold in here! As such, I’ve started wearing a pair of Quoddy “Grizzly Moc” slippers around the house and could not be happier. Perhaps the guy in your life could use something similar to keep their feet toasty warm and still look good, too.

Foul Weather Boots

Speaking of colder weather, if you regularly get gallons of rain or feet of deep snow this time of year, you know how important it can be to have a pair of “foul weather” boots at the ready. Lots of us prefer to have a pair that has both water resistant Gore-Tex linings and warming insulation.

Socks, Shoe Care, and Accessories

Socks – Business/Dress

If your giftee wears traditional business suits or upscale business casual outfits for work, consider upgrading some of their basic dress socks to higher quality, more comfortable pairs. While some guys opt for those crazy “fun” socks, I think most professionals prefer more conservative colors and patterns that can work within the tonal color palette of their clothes. Style experts: feel free to go for a pop of something complementary on the color wheel, too!

Socks – Casual

For casual wear, I’m a huge fan of adding in some fun characters, patterns, or pops of color underneath your otherwise basic chinos, cords, or denim. If your giftee is a fan of higher quality goods, consider artisanal brands like CHUP, Anonymous Ism, or American Trench that feature unique patterns or materials that you wouldn’t normally find in someone’s boring sock drawer.

Socks – Athletic

As a kid, I’m sure we all hated receiving new socks and underwear for Christmas instead of that awesome Hot Wheels track or epic video game system. However, as you get older you realize how valuable a good pair of athletic socks is and how a bad pair can ruin your day if you’re feeling uncomfortable while wearing them. When you reach that important transition point in your life, you’ll be welcomed into this club with open arms and a bottle of Aleve for all the back pain. Hah!

It might feel like a luxury to some, but upgrading those all-white Hanes athletic socks from Wal-Mart to something nicer makes a world of difference that you can actually feel every day.

Shoe Care – Trees

Shoe trees are one of the few essential shoe care items that everyone should invest in. Not only do they help keep your shoes in their proper shape as they dry out after wearing, but the ones crafted from absorbent woods like cedar or beech can also help extract moisture from the linings and deodorize them with a pleasant, woodsy scent. Every pair of shoes needs trees!

Shoe Care – Brushes

Horsehair shoe brushes are essential for removing dust, dirt, and keeping an even shine on your shoes. I highly recommend investing in a set of at least two shoe polishing/finishing brushes – one for black and one for brown. If you regularly clean, condition, and polish your shoes, you’ll want to make sure you don’t contaminate the brown brush with black polish (and vice versa). As the resident shoe nerd, I’ll actually recommend getting a third one for those suede shoes or sneakers that don’t regularly get shoe care products outside of a neutral, colorless conditioner. They’re relatively cheap and make great stocking stuffers! Note: Not all brushes are made alike. Higher quality brushes use finer grades of horsehair.

Shoe Care – Cleaners, Conditioners, and Polish

Kirby Allison, founder of Kirby Allison’s Hanger Project and shoe care nerd, says it best: “Proper cleaning and conditioning of leather shoes is essential to their long-term care. Regular cleaning prevents the build-up of dirt, waxes, and resins that can cause leather to suffocate and begin to crack.” Depending on what kind of shoes or boots you’ll be cleaning, the products can differ a lot. It’s best to consult the brand, but don’t feel beholden to purchasing their (most likely) branded cleaning products. A good neutral cleaner and conditioner is usually fine for most.

Shoe Care – Laces

A new pair of laces can really spruce up your giftee’s favorite pair of kicks. For boot lovers, consider a pair of rawhide leather laces for a more rugged look or flat waxed cotton for a more polished aesthetic. For sneakers, look at round cord or flat waxed cotton in a different color. Either way, these are a cheap and simple stocking stuffer that almost all shoe lovers will enjoy.

Shoe Care – Shoeshine Boxes

Spend: Allen Edmonds Cedar Valet Box (Empty) – $52.50 ($70)
Splurge: Saphir Shoe Shine Valet and Starter Kit – $285 ($307.25)

I try to keep all of my shoes and shoe care items well organized, but up until a few years ago, I kept all of my cleaning supplies and brushes in an old sneaker box. That’s not very Dappered. However, my mom surprised me with a lovely Brooks Brothers cedar valet storage box for Christmas a few years ago after seeing it posted here on Dappered. Thanks, Mom!

Note: If that special someone is starting from zero and has no supplies, look for one of these with some of the shoe care items included. They might not use them all, but something might be better than nothing.

Want more gift guides? Head here the growing archive of our 2022 gift guides.

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