The Best Menswear Cyber Monday Deals, According to Esquire

This year is a breath of fresh air. Normally, the Black Friday/Cyber Monday deals are released on websites well in advance. I’m talking weeks. Last year, I remember seeing everyone’s favorite Flint and Tinder waxed trucker on sale well before Black Friday. So much so that it makes the actual sale weekend fall a bit short. But not this year. All our favorite menswear brands saved the sales for post-Thanksgiving weekend. Some, believe it or not, only did Black Friday deals. If you’re here now, you missed out a little bit, but there’s still great discounts to be had.

Currently, there’s an incredible sale over at Todd Snyder. On Amazon, there’s my favorite Lacoste polo, which is actually on an outrageous sale going up to 50 percent off if you’re the right size. There’s Filson’s Short Lined Cruiser for a cool 25 percent off. Wrangler, which I’m a huge fan of, is doing 30 percent off site-wide. And REI is doing its classic “We hate Black Friday, so here’s a Cyber Monday Winter Sale,” thing.

Table of Contents

Amazon

I’m going to start this lists with my handful of favorites; then I’ll just list deals alphabetically by brand. First, Amazon. Yeah, yeah everything is Amazon now. But when Bezos is offering big discounts on Lacoste polos and Levi’s 505s, I listen.

Lacoste Original Piqué Polo

Now 38% Off

Filson

Nothing is ever going to beat the cool of a beat-to-hell Filson jacket. If you’ve been holding off on buying one, I can’t recommend it enough. Plus, Black Friday is the perfect time to get one.

Filson Tin Cloth Short Lined Cruiser

Now 25% Off

Filson Medium Rugged Twill Duffle Bag

Now 25% Off

Filson Alaskan Guide Shirt

Now 25% Off

Huckberry

I tell regular—meaning normal guys, not fashion-y dorks like me—that Huckberry is really the answer to 90 percent of what they want. All of a man’s casual wardrobe can be bought here; the only thing it doesn’t stock well is suits and tailoring. I’m seeing up to 40 percent off on the site pre-Black Friday; that’s as good as it gets, folks.

Astorflex Side Zip Berryflex Boot

Now 42% Off

Flint & Tinder Stretch Selvedge Denim

Now 19% Off

Flint & Tinder Flannel-Lined Sashiko Trucker Jacket

Now 25% Off

J.Press

There’s nowhere better for well-made classics of American menswear. It’s one of the brands I come back to time and time again. Right now, J.Press has up to 25 percent site-wide.

J.Press Made-in-USA Flap-Pocket OCBD

Now 15% Off

J.Press Light Grey Shaggy Dog Sweater

Now 15% Off

J.Press Navy Wool Doeskin Blazer

Now 15% Off

Lucchese

This is a fun one. I’ve already made it known that Lucchese is my cowboy boot retailer of choice. For Cyber Monday, the boot-maker is doing a mystery gift promotion: buy two items for $1,800 or more, and you get a mystery gift valued from $300-$1,000. My guess is that it’ll pull from the line of accessories or clothing. If you’ve been eyeing a new pair of new pair of boots, this is a fun way to get into the rest of the Lucchese catalog.

Lucchese San Antonio in Black Cherry

Lucchese Sam Swirl Rattler

Lucchese Kennedy Roper in Black Cherry

Lululemon

Any time Lululemon does a discount it’s noteworthy. The brand almost never participates in Black Friday, and it’s equally averse to any seasonal sales. This weekend only, you can get big discounts on the usual bestsellers.

Lululemon Steady State Pullover Hoodie

Now 46% Off

Lululemon Always Down Puffer Jacket

Now 43% Off

Lululemon Commission Classic-Fit Pant

Now 34% Off

Mr. Porter

If you’re not a regular Huckberry guy but a man who considers himself “into fashion” or at least “stylish,” you ought to be hitting the Mr. Porter sale. The sale is absolutely massive—over 8,000 items are up to 50 percent off, and there’s now an extra 15 percent off the standard sale section—so I’d go in with a plan. Have one item, or even one brand, you want to check out; do that and that only. My hunt is for a really good jacket—sports coat, blazer, suit separate, or whatever you want to call it. That’s what I’m showing, but you need to do some of your own hunting on this one.

Sid Mashburn Prince of Wales Wool-Linen Blazer

Now 40% Off

Rubinacci Herringbone Wool-Silk-Linen Blazer

Now 40% Off

Paul Smith Double-Breasted Wool-Linen Prince of Wales Blazer

Now 60% Off

Todd Snyder

I wrote an entire story about this one, but the Todd Snyder sale is probably the best of the weekend in terms of quality vs. quantity. Thee 30 percent discount on 800+ products is fine. What really makes it great is the level of product Todd Snyder is letting this apply to. It’s all bestsellers and fall favorites.

Crockett & Jones Cavendish Loafer

Now 30% Off

Todd Snyder x Tricker’s Suede Stow Boot

Now 30% Off

Todd Snyder x Tricker’s Scotch Grain Leather Stow Boot

Now 30% Off

The Rest of My Favorite Black Friday Menswear Deals

Alright, the rest of these I’m presenting brand-by-brand in alphabetical order. I’ll spare you a spiel on each one, but if you need some guidance, let me call out a few heavy hitters.

Del Toro, which has for a long time just been a really good rich guy made-in-Italy shoe brand, has started putting out some really lovely elevated casual clothing—all vintage Italian-inspired stuff—and a good deal of it is over 25 percent off. REI is doing its classic “we-hate-Black-Friday” Winter Sale, and there are a ton of gems if you lean outdoorsy. And J.Crew has its usual little sale going on.