The Holidays are undoubtedly a great time of the year, when everyone forgets what they were doing and gets together to have a good time (theoretically anyway, actual results may vary). But it can be a challenging time of year as well in deciding what to get everyone. Even if you know someone well it can be difficult to get them something they'll actually use. Luckily, there are some basics that everyone can use (as long as you know they don't already have it, no one wants that awkwardness).
Now, there are three tiers of gifts (if you didn't know), and it's important to know which level of gift you're going to give. The first tier is a gift for an acquaintance, a stocking stuffer, or something compatible with a larger gift. This gift is usually up to around $20, unless you're filthy rich and the polar opposite of Mr. Scrooge. The second tier is upping the ante and is usually the main gift for a family member or friend, there's no real dollar limit here, obviously since it depends on who the gift is actually for and how deep your pockets go. Typically, most people will spend up to or around $100 on these gifts however, so that's our price range here. The third tier is the top of the range gifts for your significant other, your parents, or your children. Who knows how much you're going to spend at that level, so I threw in some really interesting stuff you might want to take a look at.
Tier 1

Chambray Watch Strap, J. Crew $10
A watch strap is always a popular option to get someone, as it's a unique gift they will actually probably use. J. Crew offers up the cotton versions above and some nylon ones
here as well. Works perfectly with any Timex or similarly sized watch and is a great compliment if you are also giving the person an actual watch. Of course, J. Crew would love to sell you
their iteration.

Wool Cable Knit Boot Sock, Polo Ralph Lauren, $10.99
A pair of socks is a completely underrated gift. While we all loathed receiving them as kids, now that we're grown up I think it's safe to say we all enjoy a good pair of socks. This pair of wool socks from Polo have a vintage athletic look and work well with any sort of casual shoe. Indeed also a great side gift if you're giving them some actual boots (like the ones below).
Money Clip Wallet, Duluth Pack, $15
Chances are, we all know a big wallet guy. You know, the one who has a stack of receipts from the past five years crammed in there along with every gift and membership card he's ever accrued.
Effortless Gent has written about the
slim wallet for Primer Magazine, and slimmer wallets seem to be popping up everywhere. There's no better gift for that guy than this wallet from Duluth Pack, it combines a money clip with a card holder to form the ultimate in slim and trim carrying.

Merino Lambswool Gloves, Dots, $20
Like a pair of socks, a pair of gloves is also an underrated gift. Especially these gloves that allow you to use your touch phone in cold weather. The wool for these gloves is sourced from the United Kingdom and is woven with conductive fibers in the finger tips that allows you to use a touchscreen without taking your gloves off.

Down Vest, Land's End, $24.50
The down vest is really the perfect gift, it works with nearly every outfit and is warm to boot. It's water and wind resistant with 600-fill down insulation. It also comes in ten different colors, although if you're giving it as a gift I would stick to navy, brown, gray, green.

These canvas and leather surcingle belts are the perfect gift because they are customizable. Instead of picking one out, purchase a gift card and allow the recipient to design their own belt. It's an inexpensive and easy way to get someone something they're sure to like because they're the ones who pick out exactly what they get. It comes in enough colors and with enough design options, there's sure to be a perfect combination for everyone.
Stainless Steel Flask, Fine and Dandy Shop, $29
The flask is a gift you give to someone you know who has their own specific favorite drink. If your family member or friend only drinks small batch bourbon for instance, give them a flask like this, personalized with their initials along with a bottle of their favorite stuff. It's a surefire gift that's easy and won't disappoint.
Folding Hoof Pick Belt, SmartPak Equine, $29.95
The hoof pick belt is the coolest leather belt you could ever hope to own. It's a guaranteed conversation starter and something that really not many people even know about, much less have. This particular hoof pick is made from fine English bridle leather right here in the USA and the hardware is solid brass.
Tier 2
This knitted wool watch cap and muffler by the famous Pendleton company is sure to delight anyone as it is probably one of the best cap & muffler combos you can buy. Pendleton's wool is near bulletproof and warmer than sitting too close to the campfire. For this price, you really can't go wrong here. Goes perfect with the robe below if you know someone who is a blackwatch nut.
Scotch Plaid Flannel Robe, LL Bean, $49.50
Every guy could use a robe, although most of them don't know it. I'll admit I had never considered even buying a robe until I received one last year, now I wear it around the house all the time. This robe by LL Bean is made from Portuguese flannel and is combed on both sides for an incredibly soft feel and will keep you warm enough to lounge around the house or check the mail.

Vintage Marled Fleece Sweatshirt, J. Crew, $49.50
Heather gray is having a nice resurgence among
the style minded, and for good reason, it's really the ideal sweater to carry you through Fall and Winter. Sure there are thousands of other options, colors, styles and materials, but a simple heather gray sweater goes with nearly everything and is the perfect layering piece to complete your ensemble. J. Crew offers up this athletically inclined sweatshirt, and be sure to check out the others linked to above.
The Nadurra, Glenlivet, $60
If you know a scotch drinker, buy them a bottle of this. Of all the scotch I've ever had, the Nadurra is one of my favorites. It's a single malt that is sure to please the most discerning of scotch drinkers yet also readily accessible to the beginner. Nadurra means "natural" in Gaelic, which is in reference to it being non-chill filtered and bottled at cask strength. I received a bottle last year for Christmas, and it's become my go-to scotch for special occasions.

Bean Boots, LL Bean, $84
Bean boots are really the perfect winter gift, especially for someone who lives in a place where the winters are harsh. They are made in Maine, as they have been for nearly a century. The bean boot hasn't really changed that much over time and is a testament to dedicated craftsmanship and quality control that only a company with Bean's reputation can provide. There are several styles and types of bean boots and Maine hunting shoes, however the 8" is the most classic of all of them. It can come with or without thinsulate liners and in either tan or brown. Heck, get a pair for yourself if you don't already have some, they'll last forever and see you through the toughest conditions you can think of.
Custom Tailored Goods, Tailor Store, From $50-$100
Another great custom option is to buy a gift certificate from Tailor Store, an online purveyor of custom made goods including dress shirts, polos and chinos. Instead of just buying someone a shirt, let them design their own. With a wide range of fabric choices and colors, the combinations are nearly endless. Even if the shirt isn't for yourself, it's still fun to play designer and put together some really nice garments.
If you don't already have netflix, you're missing out. If you do have it, give the joy of endless streaming movies and shows for about the cost of your monthly cable bill. In fact, many people are canceling their cable service and going with netflix, at around $10 a month, you can't beat it.
Tier 3
Skull and Bone Velvet Slippers, Del Toro, $215
Del Toro isn't the first company to make velvet slippers, but they are quickly becoming one of the most notable. Yes, there are other brands offering similar slippers, but for the price, you're better off buying these. Lined in leather instead of silk, these slippers are more robust and can be worn around town without fear of fraying the lining. They are ideal for formal black tie events to show your dandy side, but also just as comfortable with jeans and a blazer. The jolly roger velvet slippers are a personal favorite, but there are several other designs available including the option to have yours custom embroidered with a monogram or other design. For more in depth information, check out their
review from Sartorially Inclined.
Aston Martin Racing 1959 Bag, Leadenhall, $460
In 1959 Aston Martin won the world famous LeMans 24 hours race in it's famed
DBR1 racer driven by none other than
Carroll Shelby &
Roy Salvadori. To commemorate that win, truly a thing of national pride for the England, Leadenhall created the Aston Martin racing bag. It's all leather and comes in traditional British racing green. It's not your average duffle bag, but with it's good looks and high-end pedigree it will take you and your goods anywhere you need to go with not only style, but comfort as well, knowing that your possessions are in such quality luggage.
Burris Cordovan Double Monk Straps, Mezlan, $199
Double monk straps are a pair of shoes that everyone should have. They've been endorsed here and elsewhere time and time again because they're the best pair of shoes you can own. They are, for the money, also the most versatile shoe you can buy. These double monk straps from Mezlan are made from cordovan leather, a very durable shoe material made from horse hide and are sure to last you longer than you need them to. They're also on sale, so act quickly.
Timeless Three Piece Charcoal Suit, Indochino, $399
Do you know a recent graduate? If so, there's no better gift to aid them in joining the working world than a classic charcoal suit. This three piece suit from Indochino is made to measure, just have them enter their measurements and the suit is delivered to them with a guaranteed perfect fit. The three piece is recommended, because while he won't want to wear the vest to an interview, after he gets the job, he will want to wear it around town to meetings with clients and the higher ups to show he has impeccable style and has his eyes on moving up the ladder.
Signature Grand Complication, Citizen, $1125
There are many fine watches to be had, and at many price points as well. But with incredibly fine watches comes a price, regular servicing that can sometimes cost almost 1/10 of the MSRP. That is set to change with the new Citizen Signature collection that runs on solar power and never needs a battery or servicing. Citizen has been making watches for close to a century now and is the largest watch company in the world with it's multiple subsidiaries. The Grand Complication boasts an amazing number of functions, to the level only seen on watches costing at least ten times as much. It's movement is hand-assembled, like all fine watches, and includes either a metal bracelet or an alligator strap like the one shown here. They are sure to make a statement no matter where you go, in fact, GQ recently
picked up on them. They are also relatively brand new, so there aren't too many on people's wrists yet. Note: If you're serious about buying this watch and can't find one, email me, I work for an authorized Citizen dealer.
The 714, Persol, $300
Arguably one of the most classic pairs of sunglasses you can buy, the Persol 714 is a symbol of elegance, class, style and quality all in one little package. Persol was one of the first companies to ever offer sunglasses, they've been around since 1917. They are made of some of the best materials you will find in sunglasses and are so durable it's not uncommon to find vintage pairs that are almost half a century year old. Also, Steve McQueen wore them all the time, and that's good enough for me. Note: I have a pair of
persol eyeglasses, and they have been so good they are the only company I will buy glasses from in the future.
AR.Drone, Parrot, $299
One of the few non-style related items that made this list, the AR.Drone is one of the coolest things to come out in a while. It's a flying quadcopter that is remote controlled from your iphone/ipod touch/ipad. It has a front mounted camera that displays what's in front of it on your screen while hand gestures fly the copter itself. I've seen them firsthand and I can say it's probably also one of the best time wasters I've ever seen. If you get your hands on one of these, hours will be gone in an instant. If you have a friend or family member that is the technological person and has every gadget you can think of, get them this, it will blow their mind.

Quilted Biker Jacket, Hackett London, $470
This quilted biker jacket is reminiscent of a Belstaff jacket but with a more trim and refined English style. Made of durable yet soft polyester with leather trim, it's perfect for a cruise on your bike or just about any physical activity you can think of. It also looks smart with some gray flannel trousers or khakis, an OCBD and a knit tie.
Yearly Membership, The Scotch Malt Whisky Society, $200
(from
Gear Patrol, by way of
Amateur Economist)
If gifting a bottle of scotch just isn't enough, purchase and gift a membership to The Scotch Malt Whisky Society. It invites the member into an exclusive club with access to purchasing rare scotch carefully selected and bottled by the society itself to ensure the best quality. There are also no labels denoting what distillery any of the scotch has come from, with the idea of removing any bias the member may have towards a certain brand. Renewals are only $60 a year and decrease $5 for every bottle of scotch purchased.

Smoking Jacket, Turnbull & Asser, Price Upon Request
(photo from
A Suitable Wardrobe)
Undoubtedly the most expensive item on this list, the velvet smoking jacket by Turnbull & Asser is the pinnacle of refinement and character. Available in either a single or double frog button stance, it comes in black, red, green, burgundy and navy. This jacket is the ultimate gift for the discerning gentleman who enjoys nothing but the best in life.
Hopefully this gift guide gave you some new ideas on what to get the people on your list this year or perhaps even some stuff you would like to check out for yourself. Either way, Happy Holidays!