The Ultimate Gift Guide for the Well Dressed Man

Everyone’s got someone on their list that likes to go the extra mile when it comes to style. So whether you’re looking for the perfect gift for them, or a gift for yourself to look your best at those holiday parties, here are some ideas on where to find everything for the well-dressed man.

Blank-Label.com

The guys in the corner office know, there’s nothing better than a custom fit dress shirt. Except maybe a custom fit casual shirt, that you’ve designed yourself. Pick the fabric, the style of the collar and cuffs, choose button colors, even add the military epaulets to the shoulders that are hot right now. And with their iPad app, you can also shop while standing in a store looking at much more expensive designer shirts. Because at a starting price of just $55, you can get custom for a fraction of what they charge. Gift cards are available.
From $55
Blank-Label.com

Shirts My Way

Speaking of those guys in the corner office, while they spend hundreds on their custom-sewn dress shirts, Shirts My Way can help you look the part, even if you’re closer to the mailroom than the board room.

With dozens of richly textured, high thread count, cotton fabrics to choose from, and an almost endless variety of style choices cut to your exact measurements, all starting at around $75, you can have an executive wardrobe, on a middle management salary.
From $75
ShirtsMyWay.com

Proper Suit

Suits used to all be bespoke. Gentlemen went to a tailor and had a series of fittings until their suit fit perfectly. Now we buy off the rack and then have it “altered.” Dealing with the boxiness and gaps. Unless you want (or can afford to), to spend thousands of dollars. Until now.

Proper Suit lets you own a fine bespoke wool suit, in a wide variety of colors and patterns, made to fit to your exact and unique measurements, with your specific style preferences, starting at just $450. At that price, you can suit up daily.
From $450
ProperSuit.com

Hendricks Park Voutique Personal Style Expert

So now that you know where to find great deals on clothes, how do you know what styles will work for you? Consult your own Personal Style Expert.

Hendricks Park is the perfect service for guys who hate to shop, or just don’t know what looks best on them. (Or the guy on your list still wearing “I’m With Stupid” t-shirts.) Your Personal Style Expert will meet with you virtually via WebCam, select your clothes based on fit and style, and then send them directly to your home or office. You keep what you like, and send back the rest. No postage, no problems… it’s all part of the service. If you have your own wardrobe and just need to know what to keep, what to wear together, and what just needs to be burned, they also offer a 2-hour, online, full Wardrobe Analysis.
$300 – Wardrobe Analysis (Gift certificates available)
Clothing and accessories vary.
HendricksPark.com

Jack Threads

Membership has its privileges. And in the case of JackThreads.com, that means the ability to buy designer fashions and accessories at prices at up to 80% off.

Membership is free, so you can simply enroll your giftee, but they also have gift cards so you can leave some Jack under their tree.
JackThreads.com

Nobis

Hats are back. And necessary, especially in the winter, when keeping your cranium warm is a must. No one has a better, or more unique, selection of headwear than Nobis. Located in the great White North, they know a little something about not only needing to not freeze when the temps drop, but mixing in the latest style so you can wear them to the office or dinner.
Prices vary.
Nobis.ca

Cufflinks

Nothing adds class to business attire more than a pair of cufflinks. For some, they are the only bit of self statement they are allowed to make in a button-down world.

The best collection of the unique, unusual and stylish can be found online at Cuff-Daddy.com and Cufflinks.com. (I collect cufflinks, and these are the only places I buy mine.) If your gift recipient has a hobby, a favorite sport, band, holiday, or anything else they are fond of, chances are good you’ll find a pair of cufflinks to match. And at the right price.
Cuff-Daddy.com
Cufflinks.com

TOMS Bota

These shoes were made for dressed up or dressed down winter wear. The Grey Wool (left), have an upper made from polyester and recycled plastic bottles with a faux shearling lining for warmth, while the Black has a waxed twill upper and warm woven quilted lining. And they can be worn with or without laces, perfect for traveling over the holidays.

And this is a gift that gives twice. Because when you buy a pair of Botas, TOMS will send a free pair of shoes to a child in need. And that’s a true gift.
$79
TOMS.com

IWI Timepieces

When Europe-based IWI started making timepieces, their goal was to “appeal to people who know their own mind and have got past the stage of ‘following a label.’” And they’ve succeeded. The design has its origin from the world of motorsport rally timers, and they only use the very finest Swiss automatic movements. Truly a collector’s piece, each case is individually machined (not stamped) from the finest stainless steel, numbered and then hand finished. And each range is strictly limited to a maximum of 500. Want yours even more unique? IWI will customize it with individual characteristics to suit you, like changing the bezel color, adding luminescent paint, or having the straps made of just about any material you want.
From £1450
IWIwatches.com

Phosphor E-Ink Watch

Using the same E-Ink technology you’ll find in the Amazon Kindle, the World Time and Digital Hour watches boast high-contrast, paper-like displays that are ultra-thin and curved for comfort, and require no backlight. So you can check the time in dual time zones with crystal clarity in the office, on the plane, or in the club.
From $150
PhosphorWatches.com

Kenneth Cole Touchscreen Watch

Why should your smartphone and computer be the only things that you can control at the touch of a finger? Add your watch to the mix. And on these stainless steel touchscreen watches there’s a lot to control: including 32 city world time, electro luminescent backlight, and chronograph technology.
From $125 – $175
KennethColeTouch.com

Lord Griffin Jewelry

Sometimes a guy needs to add something to remind him he’s not at the office anymore. And when it’s time for the weekend, a piece from Lord Griffon is a must.

With a medieval rock and roll edge, a small team of metal craftsmen create each piece out of pure oxidized silver, and add touches like sting ray leather accents. When’s the last time you gave the give of sting ray?
$400-$1500
LordGriffon.com