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.
Tis the season. And by now you’ve probably been walloped over the head by 82,000 gift guides. So what’s a few more? 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 well dressed Dad. Or the guy who likes to wear suits. Etc. We’ll cover all those, and hopefully a few more in the coming days.
Shoes – Heritage Boots (Casual)
- Skimp: Golden Fox 6″ Boondocker Boots – $139 (review here)
- Spend: Grant Stone Diesel Suede Boots – $295 (shown above)
- Splurge: Alden 403 Indy Leather Boots – $575
BOOT SEASON HAS ARRIVED MY FRIENDS. 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 any good boots, be a friend and get them booted and suited! Goodyear welted boots are the way to go.
Shoes – Chelsea Boots (Semi Dressy)
- Skimp: Thursday “Duke” Chelsea Boots – $199
- Spend: Grant Stone Antique Calf Chelsea Boots – $312
- Splurge: RM Williams Leather Chelsea Boots – $495 (shown above)
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 “Dunham” Derbies – $199
- Spend: Grant Stone “Fairfield” Oxfords – $295 (shown above)
- Splurge: Alden Long Wing Bluchers – $595
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 Sk8-Hi 38 DX – $90
- Spend: Nike Air Max 90 NRG Upcycled Sneakers – $140
- Splurge: Gustin Grey Nubuck Lows – $169 (Pre-Order) (shown above)
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, Mocs, and Boat Shoes
- Skimp: Sperry for J.Crew Authentic 2-eye Boat Shoes – $98
- Spend: Rancourt “Read” Boat Shoes – $250 (shown above)
- Splurge: Quoddy Made to Order Penny Mocs – $350
I know we’re discussing Holiday 2020 gifts here, but Spring/Summer 2021 isn’t that far off. If you’re an early planner, now is actually an excellent time to shop for boat shoes, camp mocs, and super casual penny loafers for your next vacation (if we can leave the house). I’m a big supporter of domestically made products, so I’m throwing two great brands from Maine in here. They’re not cheap, but they’re made very well and can last you a lifetime.
Socks – Athletic
- Skimp: Uniqlo Slub Cotton Short Socks – $5
- Spend: Darn Tough “Coolmax Vertex” No Show Socks – $16
- Splurge: Bombas Performance Merino Wool Ankle Socks – $18 (shown above)
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 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: Belle Meade “Bourbon Drinking Socks” – $12
- Spend: Red Wing “Cotton Rag Overdye” Socks – $19
- Splurge: Chup Fair Isle Cotton Blend Socks – $35 (shown above)
For casual wear, add some fun patterns, photos, or pops of color underneath your 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: Gold Toe “Harrington” Cotton Crew Socks – $22 for 6 pairs
- Spend: Orvis “Invincible Extra” Merino Wool Crew Socks – $60 for 3 pairs (shown above)
- Splurge: Pantherella “Laburnum” Merino Wool Crew Socks – $30 per pair
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. 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)
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. You should be using shoe trees in every pair of shoes, every night!
Shoe Care – Brushes
- Skimp: Allen Edmonds Horsehair Shoeshine Brush – $10
- Spend: Saphir Horsehair Shoeshine Brush – $20
- Splurge: XL Wellington Horsehair Polishing Brush – $45
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 cross contaminate the brown brush with black polish (and vice versa). As the resident shoe nerd, I’ll actually recommend getting a third brush 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 for great stocking stuffers!
Shoe Care – Cleaners, Conditioners, and Polish
- Skimp: Red Wing “Smooth Finished Leather” Basic Care Kit – $40
- Spend: Saphir Cleaning Soap ($18) + Renovateur ($24) + Pommadier Cream Polish ($21) = $63
- Splurge: Saphir “Presidential Shoeshine Starter Kit” – $140 (shown above)
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.”
Shoe Care – Laces
- Skimp: TZ Laces Round Waxed Dress Laces – $3
- Spend: Guarded Goods 54″ Flat Waxed Boot Laces – $6 (shown above)
- Splurge: Wellington Round Waxed Dress Shoelaces – $9
A new pair of laces can really spruce up your 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 your trusty sneakies.
Shoe Care – Shoeshine Boxes
- Skimp: Use an old shoe box! – Free
- Spend: Allen Edmonds Cedar Valet Box – $52.50 ($70) (shown above)
- Splurge: Alden Cedar Valet Box w/ Shoe Condiments – $250
I try to keep all of my shoes and shoe care items well organized, but up until last year, 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 last Christmas 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.
Shoe Care – Storage Bags
- Skimp: DIY! Learn to sew a clean, old t-shirt into a simple storage bag.
- Spend: Allen Edmonds Cotton Flannel Shoe Bags – $4.97 ($10) (shown above)
- Splurge: Wellington 100% Wool Melton Deluxe Shoe Bags – $35
Proper shoe storage is also important in keeping your kicks fresh for as long as possible. Soft cotton twill or flannel shoe bags are an inexpensive way to protect your shoes during the times you’re not wearing them. Are your longwings sitting on a shelf in your closet? All of that dust, dirt, and pet hair loves to accumulate on and in your shoes. Travel a lot for work like I do? Shoe bags can help keep your nice Oxfords safe from accidental luggage damage. I prefer individual bags over one large bag for the pair.
Looking for more gift guides? Here’s more of our gift guides for this year: