About the Author: Adam Terry is a thirtysomething salesman in the heating and manufacturing industry, and he’s also Dappered’s resident shoe & denim expert. He enjoys bourbon, boots, sneakers, raw denim, and working on on his
dad bod father figure.
Yes these are early this year. But by now you’ve probably heard the phrases “supply chain uncertainty” and “back ordered” more times than you had in all of your previous living years combined. So being early is the name of the game in 2021. Instead of doing a highly generalized, throw-everything-against-the-digital-wall gift guide, we’ll be breaking it up by category. Gifts for the guy who likes watches. Or the rugged type. Or the guy who suits up a lot. Etc. We’ll cover all those, and hopefully a few more over the next week or so.
NOTE ON BUYING SIZED ITEMS: Shoes come in sizes. I know. Profound observation, right? Make sure you time this correctly. Pay attention to the return/exchange time-frame & policy. Lots of retailers are doing extended return windows this year, but far from all are extending that courtesy. The last thing you want is to stick your giftee with a pair of kicks that don’t fit.
Shoes – Heritage Boots (Casual)
- Skimp: Golden Fox 6” Boondocker Boots – $139 (review here)
- Spend: Grant Stone Diesel Suede Boots – $298 (shown above)
- Splurge: Alden 403 Indy Leather Boots – $579
BOOT SEASON HAS ARRIVED MY FRIENDS. Every man, woman, and child needs a good pair of boots in their arsenal. If you’re shopping for someone that’s still wearing an entry level or basic pair of boots, look into upgrading them or reconditioning their favorite pair. If they don’t have a pair of quality boots, invest a bit and help them get booted up! Generally speaking, you’ll want to look for stitchdown, Goodyear welted, or Blake stitched boots over those that are just glued.
Shoes – Chelsea Boots (Semi Dressy)
- Skimp: Thursday Boots Legend in “Falcon” Brown Leather – $199 (shown above)
- Spend: Grant Stone Antique Calf Chelsea Boots – $292
- Splurge: RM Williams Leather Chelsea Boots – $495
Chelsea boots fill that space between the super formal Oxfords and the slightly more casual bluchers/derbies. If you’re looking for a business casual boot that pairs well with both wool dress slacks and slim fit chinos, look for a simple leather or suede Chelsea boot. Again, look for Goodyear welted pairs.
Shoes – Oxfords, Bluchers, Derbies, or Loafers
- Skimp: Beckett Simonon Eriksen Bit Loafers in Brown Pebbled Leather – $209
- Spend: Grant Stone Plain Toe Derby in Horween “Dune” Natural Chromexcel – $328 (shown above)
- Splurge: Cobbler Union Richard Cap Toe Oxfords in Black Calf – $395
If the person you’re shopping for regularly wears suits, sport coats, or upscale casual clothing, you might look into upgrading a pair of their basic or entry level dress shoes to something nicer. Just make sure you pay attention to return policies and keep your receipts should the new pair not fit as expected.
Shoes – Sneakers
- Skimp: Vans Old Skool Sneakers in “Oatmeal” Pig Suede – $70
- Spend: Beckett Simonon Morgen Retro Trainers in Leather/Suede – $159 (as seen here)
- Splurge: Rancourt Bennett Court Retro Trainers in “Flint” Kudu Leather – $250.75 w/ HOLIDAY21 ($295) (shown above, review here)
There are tons of sneakers out there to choose from, especially lots under $50, but if we’re looking to surprise that special someone, let’s make them feel really special. Look for high quality materials, upgraded components (like squishy insoles), and classic looks that pair with just about everything.
Shoes – Slippers, Clogs, and Loafers
- Skimp: Huckberry Greys Outdoor Slipper Boot in Grey/Black – $108 (shown above and reviewed here)
- Spend: Birkenstock Boston Clogs with Shearling Lining – $165
- Splurge: Rancourt Beefroll Traveler Penny Loafer in Horween Carolina Brown CXL – $285
While most of us are preparing for colder temperatures, comfort is always a personal thing. For some of us down South, we like to wear our boat shoes and penny loafers during the winter. For others, they might be looking for some warmer options made from wool or sheepskin.
Socks – Athletic
- Skimp: Nordstrom Men’s 3-Pack Ankle Socks – $10
- Spend: Bombas Original “No Show” Cotton Socks – $12.50 (shown above)
- Splurge: Darn Tough Merino Wool Ankle “No Show” Socks – $16
As a kid, you always hated getting socks for Christmas, but one day you started looking forward to it. This denotes the transition from young adult to “I now have to take two Aleve every night for my back” adult. Welcome to the club!
Upgrading your athletic socks, or those of your giftee, from those all-white Hanes 12 packs from Wal-Mart is a luxury you can probably afford now. Note: If you’re wearing low top sneakers with shorts in the summer, you should be wearing low or no-show socks that closely match the shoes colorwise. Don’t be that Grandpa that wears above the calf white socks with his black New Balance Velcro sneakers.
Socks – Casual
- Skimp: Pair of Thieves Cotton-Poly Crew Socks – $6
- Spend: J. Crew American Trench Fair Isle Cotton Socks – $20 (show above)
- Splurge: Chup Viti Cotton-Poly Socks – $35
For casual wear, add some fun patterns, photos, or pops of color underneath chinos, cords, or jeans. I’m a huge fan of some of the artisanal Japanese brands like Chup and Anonymous Ism, but Darn Tough and Smartwool are great socks mostly made in the USA. Be wary of cheap polyester socks that don’t last!
Socks – Business
- Skimp: J.Crew Merino Wool Socks – $19.50
- Spend: Darn Tough Standard Lightweight Merino Wool Socks – $22
- Splurge: Pantherella Camden Merino Wool Socks – $28.50 (shown above)
When it comes to socks for formal, semi-formal, and business casual wear, conservative styles and color choices usually take precedence. Sock height is a personal preference, but you should always aim to match the color of your socks to the color of your pants as close as possible, so think about what your recipient typically wears. Style experts, feel free to work within the tonal color palette or go for a pop of something complementary on the color wheel.
Shoe Care – Trees
- Skimp: Sof Sole Split-Toe Cedar Shoe Trees – $11
- Spend: Nordstrom (Woodlore) Split-Toe Cedar Shoe Trees – $20
- Splurge: Woodlore Epic Twin-Tube Cedar Shoe Trees – $30 (shown above)
- Big Splurge: Wellington Obeche Wooden Travel Shoe Trees – $165
Shoe trees are one of the few essential shoe care items that everyone should invest in. Not only do they help keep 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.
Shoe Care – Brushes
- Skimp: Cobbler’s Choice 100% Horsehair Shoe Brush – $12 (shown above)
- Spend: Star 100% Horsehair Professional 9” Extra Large Shoe Brush – $20
- Splurge: Wellington Extra Large 100% Horsehair Shoe Polishing Brush – $45
Horsehair shoe brushes are essential for removing dust, dirt, and keeping an even shine on shoes. I highly recommend investing in a set of at least two shoe polishing/finishing brushes – one for black and one for brown, so consider getting a couple brushes for the guy on your list. 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
- Skimp: Bickmore Bick #4 Neutral Leather Conditioner – $10
- Spend: Allen Edmonds Leather Shoe Care Starter Kit – $50 to $130 (shown above)
- Splurge: Saphir Customized Shoeshine Starter Kit – $180 to $670
Kirby Allison, founder of Kirby Allison’s Hanger Project and shoe care expert, 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 your giftee will be cleaning, the products can differ a lot. It’s best to consult the brand, so you might need to get a little stealthy to find out what brands he is wearing, but you need not feel beholden to purchase from that brand. You just need to know what they recommend.
Shoe Care – Laces
- Skimp: TZ Laces Round Waxed Shoelaces for Dress/Casual – $3.50
- Spend: Guarded Goods Round Cord Waxed Dress Shoelaces – $8 (shown above)
- Splurge: Wellington Round Waxed Dress Shoelaces – $9
A new pair of laces can really spruce up a favorite pair of kicks. For boot lovers, try rawhide leather laces for that rugged look or flat waxed cotton laces for a polished aesthetic. For sneakers, round cord or flat waxed cotton laces in a new color can add some spice to their trusty sneakies.
Shoe Care – Shoeshine Boxes
- Skimp: Florsheim Men’s Cedar Shine Box – $40
- Spend: Allen Edmonds Cedar Valet Box (Empty) – $70 (shown above)
- Splurge: Saphir Customized Shoeshine Starter Kit – $180 to $670
I try to keep all of my shoes and shoe care items well organized, but up until recently, 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 cedar valet storage box for Christmas after seeing one 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.
Shoe Care – Storage Bags
- Skimp: Zenpac 4 Pack Flannel Shoe Bags – $10.49
- Spend: Earthwise Cotton Shoe Storage Travel Bags – $18
- Splurge: Wellington 100% Wool Melton Deluxe Shoe Bags – $35 (shown above)
Proper shoe storage is also important in keeping shoes fresh for as long as possible. Soft cotton twill or flannel shoe bags are an inexpensive way to protect shoes during the times they are not being worn. If they are just sitting on a shelf in the closet all of that dust, dirt, and pet hair loves to accumulate on and in those shoes. And if your giftee travels a lot for work, shoe bags can help keep his nice Oxfords safe from accidental luggage damage. I prefer individual bags over one large bag for the pair.
Want more gift guides? Head here for the soon to be growing archive of our 2021 gift guides.