2020 Holiday Sales Guide

This year is different than any other, not only has a pandemic rocked the world, but the clothing and merchant gods have decided to spit at the thought of simply having Black Friday and Cyber Monday, and have gone straight for a whole season of sales to simultaneously save the economy and the holidays the world over. Because of this, we will be doing DAILY sales updates. Each day for the next few weeks we will be posting an announcement on our Instagram of which brand is hosting our self-selected “deal the of the day,” and we will post our top picks from that brand. So check back often because this will be an ever-growing list until the sales end or we get fed up with finding dope deals. (click on any image to purchase)

Note: purchasing items through the links provided on this page may provide What is a Gentleman a commission to help keep this site alive and Steve employed.

SatudaysNYC - 25% off sale

We’ve been over this before, so if you’re a WIAG OG then you know what I’m going to say: If you are looking for streetwear elements to add to your layering scheme for the end of Fall, all of Winter, and into Spring, then Saturdays NYC is the place to grab ‘em. They do simple, yet bold designs that are perfect hiding under a jean jacket, a bomber, or even a blazer. Our top picks:

Kiehl’s - 25% off sale with code CYBER

Kiehl’s is a skincare staple. They have been around forever, making some of the best, most dependable skincare and face products out there. We’ve recommended them before and now you can get it all at a quarter off! We recommend the bar soap, the facial moisturizer, and the facial scrub, they all work really well and smell great. Sale ends November 30th so get it while you can! Our top picks:

Wurkin Stiffs - Up to 70% off sale

Wurkin Stiffs are a must-have for every guy that wears a collared shirt to work, even when it’s over zoom. Wurkin Stiffs specialize in making magnetic collar stays that keep your shirt collar from taking flight, flipping over your jacket lapel, freeing themselves from under a sweater, etc. I always recommend these to my clients because I use them every time I wear a formal shirt, polo, or any shirt with a collar that doesn’t have buttons. Our top picks:

Travis Mathew - 50-60% off sale

Travis Mathew is THE place to grab some apparel for the millennial golfer on your list. they have bold. modern designs to their golf polos and plenty of hats, pants, and long sleeve golfing quarter-zips for the budding, rising, or tenured golfer in your life. Their clothes are high-quality, and the price right now is really hard to beat. Our top picks are:

Cole Haan - Up to 70% off sale

While Cole Haan has really gone down the “thick and comfy” sole route in most of their recent releases, which is… unfortunate. BUT, they do have some classics that should be in every guy’s closet. Right now, those classic closet staples are deeply discounted, so now is the time to get ‘em. Our top picks:

Brooks Brother’s - Up to 50% off sale

Brooks Brother’s entire site is up to 50% off and even more on their clearance items today (Cyber Monday) but we always use this sale to stock up on some sweaters. So in honor of our yearly tradition, we present to you our top sweaters that are on sale right now:

Reebok - 50% sale off with code: CYBERMON

We really only go to Reebok for their workout shoes, mostly because the Nano’s are our favorite to work out in, and right now most of them are 25% off, with some color-ways 50% off. It’s always a good idea to have a backup pair of workout shoes because if you train/run daily (or almost daily) you likely go through 2 pairs of shoes a year (or close to it). Also these masks are the best we’ve found to work out in, and right now you can get 3 for $15, which is a steal. Our top picks:

Tilly’s - Up to 50% off sale

This is the store if you are looking for some simple layer options, graphic tees, or are looking to harp back to your Volcom skater boy days. Tilly’s for those unaware is essentially PacSun on steroids. So if you are into that vibe, or have someone on your list who is, this is the sale for you. Our top picks:

Skagen - Up to 70% off sale

Skagen is a great entry-level watch company for those looking to up their assembles without spending $500-$13,000. These watches are modern, minimal, and come in styles that range from formal to streetwear. So regardless of your style (or the style of the person you are buying for) you can find something that fits. Our top picks (all are under $100):

Land’s End - 50% off sale with code SNOW

Land’s End is a comfy retailer in that most of what they make is designed for comfort. Pj’s: they got ‘em, funny mocs: yep! Base layers for the winter: You betcha. Right now, all of the normally priced items are 50% off so if you want to get the family a matching set of PJ’s on Christmas morning, now is your chance. Out top picks":

Bodum - Up to 55% off sale

If you have a coffee lover or someone who has just moved into a new place and in the market for some design-centric kitchenware or to-go containers, then this is the sale for you. Bodum carries some of the best coffee paraphernalia in the biz, with matte black kettles, a thousand different brewing methods, and a variety of accouterment to help organize and store your coffee-related items. Our top picks:

Orvis - Up to 50% sale

Orvis is for the guy who loves to be outside but likes to do it in style. They are our preferred place to get Barbour jackets/vests, etc. and they have a pretty stellar line of their own Fall/ early winter coats. This sale is the perfect time to get a new quilted, or field jacket for the inevitable walks you’ll need to take just to get out of the house. Our top picks:

All Saints - Up to 50% off sale

All Saints is the New York “cool person” ensemble retailer. Leather jackets: they got-em, shirts ripped in just the right way: those too, weird fashion-first designs on button-downs: yep. All Saints, in our opinion, is normally a bit over-priced for what they offer, but when there are sales like these, it’s hard not to look and go “Yeah this feels right, I think I’ll finally get myself a leather jacket.” But hurry up because these sales never last long. Our top picks:

Grayers - 40% off with code HOLIDAY

Grayers is probably the retailer we most commonly look at and say “oh man that’s a cool sweater, I want one.” They almost never have a sale on the things you really want, but today is a the day! Use code holiday right now before the sale is over and all the smalls, mediums, and larges are gone. Our top picks:

Nomatic - Up to 50% off

While traveling isn’t really at the top of everyone’s list right now due to the pandemic, having the right gear you’ll need to make those first trips (hopefully come May) easier will feel like a god-send. Nomatic has the best tech-focused bags out there. If you are a consultant who travels, a creative that totes around a decent amount of gear, or someone that just loves organization, these are the bag you need. Our top picks:

Ted Baker - Up to 60% off

Ted Baker is the for the guy who lives in business casual, and loves a modern cut. Most of their apparel is a euro-inspired contemporary take on classics. So if you have a guy on your list that likes to be bold, but enjoys the familiar, this is the sale you need to take advantage of. Our top picks:

Urban Outfitters - Up to 25% off

If you are trying to be a rising TikTok star, then this sale is for you. So grab some tie-dye, ripped jeans, a few dance moves, and pop-up text boxes and get after some clout. These are our top picks for the gen zebras.