Skip to main content
  1. Home
  2. Fashion & Style
  3. Deals

Best Labor Day Sales on Men’s Clothes, Shoes, Accessories, and More

Labor Day is almost here, falling on Monday, September 2 this year. While some students may not be excited at the prospect of another school year, many of us are looking forward to relaxing and enjoying that three-day weekend along with the many annual Labor Day sales that always spring up as the summer draws to a close. Big blowouts like Prime Day and Black Friday are great for scoring deals on pricey electronics, but Labor Day and back-to-school promotions are among the best opportunities of the year to buy clothing, accessories, and outdoor gear at big discounts.

Whether you’re a student who is suiting up for another year on campus or you’re just hunting for some fall essentials in anticipation of cooler autumn weather, there’s never a bad time to fill out your closet a bit more. To help you out, we’ve sniffed out the best Labor Day sales on men’s clothes, footwear, and more and have gathered them all right here along with a handy guide that lays out what to keep your eyes peeled for (and what pitfalls to avoid) while shopping.

Recommended Videos

Best Labor Day clothing sales for men

Fall is fast approaching and Labor Day sales offer a fine chance to stock up on cool-weather staples like corduroys, jeans, chinos, and long-sleeve shirts (not to mention accessories such as leather belts that you might not wear as much during the summer). However, the changing of the seasons is also a good time to score deals on summer stuff that retailers will be trying to get rid of, using Labor Day sales as an excuse to clear out their remaining last-season stock.

Labor Day sales on clothing are also a good opportunity to smoke out deals on pricey items like shoes. This is particularly the case for heavier fall and winter footwear like leather boots, which tend to be a lot more expensive than those sneakers you’ve been rocking for the past six months.

When are the best Labor Day clothing sales?

labor day clothing sales
Image used with permission by copyright holder

Labor Day 2019 lands on Monday, September 2, and since it’s falling so early in the month this year, this means that the three-day holiday weekend actually starts in August (specifically on Saturday, August 31). Labor Day sales will almost certainly run for the entirety of this three-day weekend, so at the very latest, you’ll want to keep your eyes open for deals starting on Friday or Saturday at the end of this month.

Be aware that many of these Labor Day sales will typically begin about a week before the holiday itself, though, and quite a few are already live. Others will also run through the week after Labor Day, so look out for those as well. Finally, don’t make the mistake of limiting your deal-hunting to the internet – your local brick-and-mortar outlets will be offering their own promotions and could have some hidden gems on things that might already be out of stock online.

Tips for shopping Labor Day sales on clothing and accessories

As with all online shopping, you need to keep your wits about you when combing through the Labor Day clothing sales if you want to find the best deals. The golden rule of deal hunting is making sure that a deal is actually worth it. If you’re shopping at a retailer you’re familiar with, you’ll probably know if something is a good score. If you’re perusing an unfamiliar retailer or one that sells many different brands (like Amazon or REI), be sure to check out other outlets to compare prices. You might even find a better offer elsewhere.

When shopping websites like Ebay, always exercise your due diligence to avoid shady sellers. Look at feedback and return policies (this is also true for Amazon, which hosts a ton of third-party sellers – something too many shoppers are still unaware of). And lastly, go in with a budget in mind and stick to it. It’s a good idea to even make a list of what exactly you’re looking for, and what you’re willing to spend per item, so you don’t let advertisements or over-excitement bait you into spending too much.

Lucas Coll
Former Deals and News Writer
Lucas Coll has been a freelance writer for almost a decade and has penned articles on tech, video games, travel, cars, and… Read Full Bio
The 7 best Canada Goose jackets for men this winter
Canada Goose

For three quarters of a century, Canada Goose has been one of the go-to places for luxury snow gear. There are a lot of choices you can make when looking for the best coats or the things you need to survive the cold weather. Of course, there is also the dozens of brands that you can look for, and it can get relatively overwhelming. In an oversaturated industry, a brand born in the snowy plains of Canada is the best option. We took the time to do a deep dive for the best Canada Goose jackets for men to come up with a list of the top seven you need for the 2025.

Read more
The best casual watches for men (to upgrade your everyday style)
Work wear blues watch close up

Watches are more than a tool. They are more than an accessory. They are the kind of tool and accessory that make a statement. They are an expression. They are a statement. A man can look incredible: the right top, the right bottom, great shoes, great hat. The wrong watch can ruin a look, or even the whole essence. Here is the rub: the wrong watch can be subjective. For instance, most people will tell you that a Timex broken watch isn’t the right watch for a pinstripe power suit. However, it was my grandfather’s watch, and I wear it anytime I need him and his guidance. The point? That is never the wrong watch. Once you find a casual watch that works for you, it will be your everyday wear and will never be the wrong watch.

That is what I collected here: The best of the casual watches you can pick up today that will become your everyday wear.

Read more
Audemars Piguet launches pre-owned program to rival the titan of the second-hand watch market
Audemars Piguet

Rolex has dominated the watch world for nearly a century. The industry is a deep and complicated web of luxury houses and independent hopefuls. While brands like Patek Phillipe and Cartier vie for their place on the podium, Rolex holds a death grip on the chronophile’s aspirational collection checklist. But Audemars Piguet has decided to challenge them somewhere most other brands are deciding to ignore: the pre-owned market. Now, while something like the Royal Oak is an icon among enthusiasts, AP launching their own certified pre-owned marketplace to chase the reported $1 billion Rolex pie will certainly upset the market.

Like I said, it is a deep and complicated web, so I sat down with a horological expert and founder of WatchGuys, (317K on Instagram), Robertino Altieri, to have him walk me through what this means for watches and their passionate collectors.

Read more