Men’s Holiday Gift Guide 2020

This year is a little bit different because… pandemic. So these choices are more geared toward sending directly to the receiver instead of handing to them in person and they’re also options that will work for everyone (including yourself!) regardless of age, size, budget, location, etc. We hope you have a happy holiday season!

Cashmere Beanie

Everlane – $46
J.Crew – $69
Italic – $30

Now that we’re living in Paris and are experiencing an actual winter, it was time to stock up on a luxurious beanie (or 3) and there’s nothing better than warm, soft cashmere to keep a noggin warm. All the options come in a multiple colors and our favorite part is that they are one-size-fits-all and are unisex.


Aer Fit Pack 2 – $135
Peak Design Everyday Backpack – $200 to $290 We have a bit of an ongoing feud in our house. Ashley (and by extension her clients) are Fit Pack lovers. She likes them because the design is minimal and utilitarian and feels that the price is great, plus usability and comfort. While Dorian is not a hater of Aer, he finds their lack of customization not to his liking so he prefers the Peak Design option(s) for the oodles of pockets, side zips completely open on both sides for access to all parts of the bag and configurable storage areas. He uses 30L size, but they also make it in 20L if you want something a little smaller or the gift receiver has a smaller frame. If backpacks aren’t your thing, don’t worry, we’ve got something for you on this list, too – keep scrolling.

Buy-It-For-Life Pen

Ti Click EDC Pen – $100 Dorian has been an owner and personal user of this Titanium pen for the past few years and it’s amazing because it works with 100+ ink refills. So if you have a particular color, type of ink or thickness you like, it will work with this pen. While it’s a little pricey at $100, this thing is Buy-It-For-Life quality and looks as good as the day he bought it and comes in 3 different color options.


L.L.Bean Men’s Wicked Good Moccasins – $80 We’ve been wearing and recommending these moccasins for years and no other slippers we’ve tried have been as comfortable or kept our feet as warm. Their stitching is durable, and the suede shearling upper means he won’t have issues with the moccasins wearing thin or splitting open on top. And L.L.Bean backs these slippers with a one-year guarantee, if anything should happen in that time (although we don’t anticipate it).

Quality Dress Socks, Ties & Pocket Squares*

Southern Scholar – $20 to $100+ for gift sets
Get 20% off with offer code: AW20 Accessories like ties and pocket squares, and especially socks are something that a lot of guys overlook. As the saying goes:
Never skimp on things that separate you from the ground:
tires, shoes, socks and mattresses.

All of Southern Scholars products are made of the finest materials and with attention to detail that showcases the excellent craftsmanship. Having worn the socks while walking for miles around Paris, Dorian says they completely live up to the hype and they’re super comfortable, form fitting, have reinforced toes and heels, and are also antimicrobial, moisture wicking & breathable.

Their whole line of products come in great colors and patterns – from simple solids and up to stripes, polka dots and beyond. But our favorite part is their guarantee – if they’re not the best dress socks you’ve ever worn, you can keep them for free. Talk about standing behind your product!

Check out their Perfect Pairing boxes, which include a pair of socks, tie and pocket square, which are great gifts for the men in your life, as well.

Briefcase/Messenger Bag

Metropolitan Slim Brief by Coach – $595 We’ve recommended this bag for many, many years now and we’re going to keep recommending it as long as they keep making it. The briefcase is super functional with a clean and classy design, comes in different colors and is made of high-quality leather – it’s basically perfect.

For a cheaper option that ticks most of the boxes, check out this $200 one.

The Best Insulated Mug, Thermos or Water Bottle

Zojirushi – $22 We’re obsessed with the Zojirushi Stainless Steel Mug. The coffee, tea or water fan in your life will be equally enthused with its vacuum insulation, the Zojirushi keeps beverages hot or cold for hours and thanks to the secure lid-locking mechanism, the Zojirushi doesn’t spill a drop. The added benefit is they come in different colors and sizes.

Leather Key Cover – $45

Bellroy – $45 If you’re shopping for someone that’s hard to buy gifts for this is a perfect present because most people don’t think about improving their key situation. We’ve used and recommended this to friends and family for years and have to say that like the Zojirushi mug above, until you use it, you didn’t know you needed this in your life. It’s got a slim design, magnetic closer and just looks really classy.

The Best Face Masks In The World

MaskLab – KF Style – Many Colors, Unisex – $10- $20 After trying a bunch of masks over the past year, these are by far our favorites. They sit well on all face sizes, don’t smash your nose and hardly move when talking due to the adjustable top and bottom flaps. Our favorite part is that they come in a variety of colors and patterns.

Non-Amazon E-Reader

Kobo Clara HD – $99.99 If you’re looking for an e-reader that isn’t locked into the Amazon universe or doesn’t ads on the lockscreen, look no further than Kobo’s lines of e-readers. You can buy books from anywhere online sand easily add them to your Kobo device or if you like simplicity, you can use the Kobo store to buy all the same Amazon books.

Leather Dopp Kit

Italic Men’s Leather Dopp Kit – $80 When everyone can travel again, there’s nothing classier or better for organizing your travel toiletries than a dopp kit. Italic’s version is clean and simple and made in the same factories as some of the top designers.

Last Minute Gifts

Blinkist subscription – $50 to $100 Having been a paid user of theirs for the past year, if the person on your list is into non-fiction or self-improvement books, this is a must-give. The service takes all the popular books in those categories and distills them down to their essence via “blinks” and you can “read” a whole book in about 15 minutes. The best part is that you can read the blinks, or listen to them, so there’s multiple ways to consume the content.
Spotify subscription – $99 Simple, one-size-fits-all and who doesn’t love having a huge catalog of music and recommendations at their fingertips? We don’t have many subscriptions, but this is one we happily pay for without question.
Atlas Coffee Club subscription – $60 If you’ve got a coffee lover on your gift-giving list this year, give them the gift of great coffees delivered right to their door. There’s much more to this company than it appears on the surface, so definitely check them out.

*This item is sponsored but having tested all their products, they’d be recommended even without being a sponsor.

3 Boot Styles Every Man Should Own

Lace Up Boots

A good lace up boot is definitely a must-have in your shoe rotation.There’s 3 types of lace up boots that you should consider, based on how you’ll wear them or what look you’re going for:

  • Work or Casual
  • Dress
  • Mixed Materials (we’ll call them Fashion boots)

The Work Boot

A work boot adds a rugged, masculine touch to your casual outfits and typically has a chunkier profile and more rugged sole, which you obviously want for added grip in rain or snow.

The Dragon boot by Taft. Click the picture for details.

Unless you’re going for a specific look, work-style boots shouldn’t be worn with your more dressed-up looks because the profile is more geared toward casual outfits. If you want a more rugged boot that looks more worn in, then highly recommend the above Taft work boots. The overall look of the leather, along with the chunkier rubber sole will compliment your casual layered looks during the Fall and Winter. The darker brown color a my favorite because it can easily be worn with your earthy/fall colors or black outfits as well. Here’s a great way to style the Dragon boot in an outfit:



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Dress Boot & The Two-For

This type of boot adds a sleek, sexy and sharp touch to your more elevated outfits.

The Rome boot by Taft. Click the image for details.

Notice how the profile is less “bulbous” and the sole a little thinner than the casual boot? That’s one of the ways you can distinguish a dress and casual boot (the type of soles also determines this.)

If you’d like a dress boot that can also work with casual outfits, I recommend getting a boot with tumbled leather, like the image above, which enables it to work in both casual and more elevated, dressy outfits. The texture adds just a hint of casualness to the boot, this is why it is able to work with both situations. The sole can be either leather or a thin rubber profile like a Dianite sole. This specific boot comes in a variety of colors, so choose whatever you prefer, but we’re always going to be partial to black and brown. A simple, classy way to style this boot is like this:



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The Fashion Boot

If you want a boot with personality, then getting something with mixed materials is perfect.

The Holt Boot in Espresso by Taft. Click image for details.

There’s a ton of “fashion boots” out there that incorporate materials like tweed, suede, and wool in their leather boots. I love these tweed one’s by Taft that Dorian’s wearing in the image below because they’re the perfect balance of style and trendiness without being tacky. Wear these with jeans, wool trousers, chinos and suits whenever you want to inject a bit of flourish into an outfit.


Chelsea/Slip-On boots

There’s two designs to your Chelsea boots

  • The classic Chelsea that you’ve come to know and love.
  • The Jodhpur which is recognizable by it’s wrap around strap and buckle detail.

Let’s start with your classic Chelsea design – Suede Chelseas pair well with your casual Fall/Winter looks, as the texture compliments the thicker materialed clothing you’ll be wearing during the chillier months. But opt for leather Chelseas if you want a dressy pair as the leather’s sleekness invokes formality.

As far as Jodhpur’s, the same rules apply as far as suede vs leather. These are great if you want something different than your standard Chelsea boots, but they’re virtually the same in how you style them, so just go for whichever style and materials you like best.

Here’s the links to the 3 boots:

Outback | Hiro | Dylan


Here’s a great way to wear these types of boots, there’s also a few other pictures featuring the Outback boot on the Instagram account:



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Chukka Boots

Consider these as a great casual shoe option when you don’t want to wear sneakers or full lace-up boots.

The Milliken Chukka by Johnston & Murphy

They’re certainly faster to put on than lace up boots, so if ease is what you’re after than consider these. As far as styling goes, chukkas really shine when worn with chino pants and jeans. A medium to dark brown and black are fantastic starter choices and then from their you can experiment with color.

Here’s a great way to style your chukka boots:



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Men’s Minimalist Summer Wardrobe

Chino Pants

Tan & Navy

Favorite 1 | Favorite 2 | Favorite 3

Polo Shirts or T-Shirts

Navy & Heather Gray

Polo Favorite 1 | Polo Favorite 2

T-Shirt Favorite 1 | T-Shirt Favorite 2

Linen Long Sleeve Shirts

White & Navy

Favorite 1 | Favorite 2

Low-Top Sneakers

White or Blue

Favorite 1 | Favorite 2

Woven Belt

Dark Brown

Favorite 1 | Favorite 2

Leather Penny Loafers or Suede Driving Mocs


Driving Moc Favorite 1 | Driving Moc Favorite 2

Penny Loafer Favorite 1 | Penny Loafer Favorite 2

Lightweight blazer


Favorite 1 | Favorite 2

No-Show Socks


Favorite 1

Perlon Watch Strap

Navy & Brown

Favorite 1

Baseball Cap


Favorite 1

Panama Hat

Favorite 1 | Favorite 2


Tortoise Shell Brown

Favorite 1 | Favorite 2

Chino Shorts


Favorite 1 | Favorite 2



Favorite 1 | Favorite 2

9 Summer Accessories Every Man Must Have In 2020

We’re going to briefly go over the essential Summer accessories every man should consider grabbing for this time of year. If you haven’t downloaded the free Summer Ebook, you’re missing out!


Woven Belts

With your warm-weather outfits, there’s nothing that looks better than a woven belt. Either in leather or fabric. For a little extra casual flair, get the belt a little longer and let it dangle a bit. As for colors, you can have some fun with them and get some browns, navy or even gray options.

The Tie Bar | Uniqlo

Chain necklace

David Yurman | John Hardy

Tote Bag

L.L.Bean | J.Crew


We talked about it in our  Summer Style Mistakes Video and now it’s time to pull out the brown/tortoise shell and/or colored frames to go with your lighter-colored clothing.

Warby Parker | Oliver People’s


Ball caps


Panama Hat

Brooks Brothers | Ted Baker

Slim Cuff/Bracelet

Since you’ll be wearing more short-sleeved items or rolling up your shirt sleeves, it’s time to bust out the wrist jewelry.


Fun socks or No-Show Socks

Happy Socks | Uniqlo

Loafers or slip-on sneakers

Whether you go a little more polished and formal with a leather penny loafer of suede driving moc or a pair of slip-on sneakers, it’s the beginning of slip-on season!

Tods | Vans | Kenneth Cole |

Fabric or colored watch straps

If you’re not a jewelry guy, then swapping your watch bracelets or straps for fabric, suede or even rubber straps is a fun, quick and easy way to enhance an outfit and change up the appearance of your watches.

Great Budget Straps

11 Men’s Summer Wardrobe Essentials for 2020

These are our favorite Summer Wardrobe Essentials you should grab for this time of year. Below are our favorite picks for each item discussed in the video. If you haven’t checked out our detailed Summer Essentials Ebook, you’re missing out!

Short sleeve Shirts

Uniqlo | H&M | Brooks Brothers


Koio | Converse | Adidas

Linen Long Sleeve Shirts

Uniqlo | The Tie Bar


Tods | Kenneth Cole | Allen Edmonds

Bomber Jacket


Polo Shirts

The Tie Bar | H&M


Brooks Brothers



No-Show Socks

Bombas | Uniqlo

Watch Straps

Dorian’s favorite place for cheap straps.
He specifically likes the perlon, cloudy perlon and canvas straps.