Get Your Guy a Winter Outfit

Ladies, this post is for you.  Maybe your boyfriend or husband has a birthday coming up and you’re considering gift possibilities.   What would be cool to get your Capricorn or Aquarius or Pisces guy?  And then there’s Valentine’s Day, which is another opportunity to find something unique and interesting he would enjoy.

The operative word above is “cool.”  It’s winter.  And the season is going to be around for awhile yet, which means continued cold weather.  Why not get something both practical and stylish in the clothing line? 

Get him some winter clothes he can feel good about wearing, both in terms of function and as a welcome addition to his wardrobe.

When it comes to clothes, men tend to fit into two categories:  those who don’t have much of a clue about style, fabric, and color and are happy to let their wife or girlfriend pick stuff for them to wear, or those who are more particular about their look and prefer to choose their own attire.

For either type of guy, this post covering a cool winter outfit will work.  Because I’m going to suggest clothes that, even if he likes to shop for himself, he might not have considered (because he hasn’t heard of them).  And if he prefers that you make suggestions about what he wears, then you can be confident that the brands reviewed here are high-quality.

In the former case, you might actually help expand his clothing horizons a bit (while giving him stuff he’ll enjoy wearing), and in the latter case, he’ll look good, have a warm outfit, and own clothes that will last awhile.

Now is a good time to shop for winter apparel

It’s a good time to shop for winter clothing now because, believe it or not, retailers are clearing out the last of their winter stock and thinking about getting ready for spring.  In many cases prices have been slashed on men’s clothes for this season (even though winter isn’t even a month old). There are numerous sales happening.  So it’s a good time to find some bargains.  (And guys who are reading this…it’s not a bad time to shop for yourself.)

So here’s a head-to-toe winter outfit, with some essential style elements.  It will include a sweater, T-shirt, jeans, socks, and boots.  Even shades.  I’ll offer a couple of different options on some of those items because, you know, one size does not fit all.  Nor one style.  And, of course, any one of these garments will work by itself.   Because you might not have it in your budget at the moment to go for the whole enchilada.

In any event, don’t wait to acquire the following men’s clothes, because the best pieces of winter clothing are disappearing fast from the shelves.

First:  A Sweater

Sweaters can be a tricky thing.  Some can look dorky.  Some can be poorly made.  Some can be both.  But a well-made, warm sweater with a classic design is a go-to item of winter apparel that can be worn for many years.  The key is to find an interesting style that is not outlandish, made by a reliable brand using high-quality materials.

The first sweater suggestion is the Bugatchi ½-zip Mock Sweater.  It’s available from Peter Glenn Ski and Sports, a retailer of high-end clothing and outdoor sports gear.  (All the retailers mentioned here have also been vetted by me as being trustworthy, with reliable customer service and good return policies.)  The Bugatchi ½-zip Mock Sweater is pictured below:

The Bugatchi Half-Zip Mock Sweater for men is a sweater that your guy can wear in a variety of situations.  Click to see see and purchase it from Peter Glenn Ski and Sports.

Click to see the Bugatchi Half-Zip Mock Sweater at Peter Glenn


 The Bugatchi Half-Zip Mock Sweater is made of 100% merino wool in a sophisticated multi-tone knit, with ribbing at hem, cuffs, and collar.  As with all the men’s clothing designs from Bugatchi, it is well-made, with nice details. 

Clothing designer Bugatchi Uomo has been earning a reputation for its bold, well-crafted designs in recent years, particularly with their line of men’s shirts.  This sweater is no exception.  Their design philosophy is to create clothing that is trend-setting and affordable using the finest fabrics, with particular attention to quality fabrication.  You may not have heard of Bugatchi (which is based in Boca Raton, FL) before now, but their clothing is being carried by some of the finest menswear stores in the country.  There is a reason Peter Glenn offers Bugatchi clothing for men — it works, is well-made, and looks good.

Here’s a second sweater to consider — The Penny Crew Sweater by Penny Stock — available from Revolve Clothing…

A versatile, warm sweater is a staple of a man's wardrobe, especially during the winter.  The Penny Crew Sweater from Penny Stock fits the bill when it comes to a stylish, versatile sweater he can wear in any season.

The Penny Crew Sweater by Penny Stock is a versatile sweater. See it at Revolve Clothing.


This versatile, navy-blue, horizontal-striped sweater will never go out of style.  It’s made of 60% cotton and 40% acrylic.  The 9GG construction provides a rich and uniform texture.  This is a warm sweater, but not too warm, so it will work for a wide variety of conditions, from fall through winter to spring.

Penny Stock clothing company is a brand that, like Bugatchi, is dedicated to offering iconic style at true value (their symbol is Abe Lincoln).  Penny Stock has been receiving favorable notice in the press, including GQ, Lucky magazine, New York Magazine, LA Canvas, and Antenna.  Write-ups have praised Penny Stock’s affordable and egalitarian line of clothing.  As you can see from the photo above, the Penny Crew Sweater will look good on just about any guy.  It can be worn with jeans (see below) or chinos or olive drab cargo pants…  The link goes to Revolve Clothing, which, since its founding in 2003, has become a go-to online source for 500 of the best designer brands of men’s and women’s clothing, shoes, and accessories.  The only problem is that Revolve’s stuff is so popular it tends to sell out fast, so if you like this sweater from Penny Stock, don’t wait to get it.

Second:  A T-shirt

You don’t really want to wear a sweater with nothing underneath, so how about an interesting T-shirt to provide the layering foundation?  Here’s just the thing — a hemp T-shirt from ONNO.

A T-shirt made of hemp will provide a unique layering option for your guy's winter outfit.  Hemp is better in several ways than cotton.  Learn more at ONNO's site.

Men’s hemp T-shirt in charcoal — $26 from ONNO.


Aside from the fact that a T-shirt made of industrial hemp is cool in and of itself, a hemp T-shirt has some advantages over a cotton T-shirt.  Hemp fibers are more durable than cotton, they are naturally antimicrobial (helps if your guy overheats), they wick moisture better than cotton, and provide better UV protection.

Hemp T-shirts from ONNO are well-made and comfortable.  They are a blend of 55% hemp and 45% organic cotton.  ONNO strives to make all its clothing as environmentally-sustainable as possible.  They also offer T-shirts for men and women made of 100% organic cotton, and also from bamboo.  (If you’d like to learn more about their bamboo T-shirts, see my review here.)  Hemp is cool for a variety of reasons.  You can get a lot more info — and purchase their unique, excellent clothing — on the ONNO site.  Pair a hemp T-shirt in one of ONNO’s 11 color options with one of the sweaters above and I guarantee your guy will be well on the way to a one-of-a-kind outfit.

 Third:  Jeans

What about below the waist?  For winter you need something durable, versatile, and preferably stylish.  In a word, denim jeans.  Here you’ll find a couple of options. 

The first pair of jeans is on the edgier side, stylewise, while featuring quality construction and durability:  Voi Jeans Kempsey AW12 Multi-Pocket Denim Jeans. 

Voi Jeans makes interesting and high-quality jeans for men, including the straight-leg Kempsey AW12 Multi-Pocket Denim Jeans, which you can get direct from their site.

Kempsey AW12 Multi-Pocket, Straight-Cut Denim Jeans from Voi Jeans


These jeans from Voi Jeans are a straight-leg style, which should work for most guys.  Voi Jeans also makes men’s jeans in slim and loose-fitting cuts

Voi Jeans is an English company specializing in making jeans that are distinctive and functional.  Unusual touches on the Kempsey AW12 Multi-Pocket Jeans include front thigh pockets (7 pockets total), a cinch-back waist, and the faded “V” logo on the back pockets.  These jeans are inspired by a workwear style.  For a more traditional 5-pocket, straight-leg pair of jeans, take a look at Voi Jeans Company’s Bowen AW12 5-pocket Denim with printed swirl, in a dark wash with contrasting stitching.

Voi Jeans has been making interesting, high-quality men’s clothing since 1988.  Since they established an online presence in 2009, they are beginning to be known throughout the world.  In 2010, Drapers magazine, England’s 125-year-old fashion-reporting journal, named Voi Jeans as one of the top 10 best menswear lines, ahead of brands such as Diesel.  When you go to the Voi Jeans site, you’ll see the option to click on a button to optimize shopping for your country, including the USA, where prices will be shown in dollars.  In many cases, international shipping on orders is free, via Royal Mail.

Voi Jeans (“voi” means roughly “you all” in Italian) is a brand that hardly anyone you know will be wearing.

Voi Jeans

The second jeans option is quite different from Voi Jeans, but still very appropriate for winter:  Carhartt’s Relaxed Fit Straight-Leg Flannel-Lined Jeans. 

Carhartt makes some of the best jeans for men, including these relaxed-fit, straight-leg, flannel-lined jeans.

Flannel-lined jeans keep you warm in the winter. Carhartt makes some of the best.


This is a warm, sturdy pair of men’s jeans made of 15-ounce, 100% cotton denim, with a cotton flannel lining for warmth.  (It’s amazing how warm you can be when you add some insulation to your pants.)  Carhartt also makes a fleece-lined version of these jeans for even colder conditions.

Carhartt is the iconic brand of clothing worn by workingmen around the world.  Everything about the company is geared toward quality and performance.  Carhartt jeans don’t look bad, either.  And these warm winter jeans are only $50. 

Here’s a customer review for Carhartt’s flannel-lined, straight-leg jeans:

“I bought these for the winter months where I live in New England.  I wear them snowmobiling and to work and they keep me nice and warm!  Best fitting and feeling jeans I have had in a long time.  Not to mention that they are over a year old now and look like new still!”

If you’d like to know a lot more about Carhartt and men’s jeans in general, see my extensive post The Denim Guide:  5 Brands of Men’s Jeans that Outperform the Rest.

Fourth:  Socks

There’s nothing like a nice, warm, well-made pair of socks on a cold winter day.  You can find some excellent socks for whatever your guy will be doing — from going to the office to splitting half a cord of firewood — at Sierra Trading Post, and all for good prices.  Such as the Byford Donegal Rib Mid-Calf Men’s Socks, which are made in Italy from a luxurious blend of merino wool and silk (pictured below in charcoal):

Some of the best socks for men are made by Byford, including thse Donegal Rib Mid-Calf socks, which you can get in various colors at Sierra Trading Post online.

Byford Donegal Rib Mid-Calf Socks at Sierra Trading Post


You might expect to pay a lot more for these socks than $15.  But again, it’s Sierra Trading Post, one of the most reliable and diverse retailers of gear and clothing on the Web, with prices that are easy on the wallet. 

Based in England, Byford has been making top-of-the-line socks since 1919.  You cannot go wrong with any pair of Byford socks.  These Donegal Rib Mid-Calf Socks feature a rounded heel for better fit and a smooth, flat, comfortable toe seam.  But the important thing is that warm blend of wool and silk.  You can get them in several colors.  And they’re on closeout for under $12.  Now that’s a deal!

If the Byford Donegal Rib Socks are sold out, Sierra Trading Post carries a number of other top brands of socks for men, including SmartWool, Falke, Point6, Icebreaker, and Bridgedale.  You can find any number of high-quality sock options for your guy, at prices that make it easy to buy two pair.

 Fifth:  Boots

In winter you need a good foundation, so a guy appreciates boots.  They’re versatile and can handle nasty weather variations. Ideally, you want the most rugged yet good-looking pair you can find — boots that will perform for diverse uses, from drinks after work to a hike through frosted and stubbly fields outside town.  So you get 268 Boots from Blundstone:

Blundstone makes some of the best, most versatile men's boots in the world, including the lace-up 268 model, which is available from Zappos.

Blundstone 268 Boots, available from Zappos


Blundstone boots have a burly outsole that will handle just about any abuse (they’re a recommended favorite of the guys at Outside magazine), leather uppers with twin goring panels, and twin-needle reinforced stitching.  They’re made in Tasmania, Australia (which makes them even cooler).  Here’s a Blundstone video:


I recommend you get the Blundstone 268 Boots from Zappos, and benefit from the best customer service on the Web.

 Sixth:  Sunglasses

We’ve been working on this winter outfit from head to toe, but let’s top it off by going back upstairs and finishing with a cool pair of shades.  After all, when you’re wearing your stylish clothes and boots around town or around the world, you don’t want to be squinting from glare off ice, snow, or flooded rivers.  So you’ll need some top-of-the-line sunglasses, preferably in an aviator style, which looks good on just about anybody.  In this case, get the Windspeed Sunglasses from Revo.

A pair of cool aviator shades will round out your guy's winter outfit, and you can't get a better pair of sunglasses than the Windspeed shades from Revo, available at Zappos.

Revo’s Windspeed Sunglasses are a classic aviator style with cutting-edge performance features.


Revo’s Windspeed Sunglasses incorporate a number of sophisticated features that ensure good performance under a variety of demanding conditions, including Crystal Lenses for distortion-free clarity, an anti-reflective coating, high-contrast polarization, and a durable, 5-alloy frame.  The Windspeed Sunglasses are available with a number of lens and frame options and include adjustable nose pieces.  These are a top-flight pair of aviator shades and you can get them from Zappos.

And now your guy’s journey to the stylish and functional side of winter apparel is complete.

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