So you receive countless emails from brands about their seasonal sales.
Who doesn’t love a good deal?
It can be tempting to buy a jacket you’ve had your eye on for a while and is now 50% off. But mindless shopping during sales can get you into trouble.
I’ve seen clients waste thousands of dollars on clothes that don’t fit them (or, frankly, are ugly) just because they were on sale!
The point of a sale is to save money! Not to end up with a pile of unworn items that you bought because they seemed like a bargain at the time.
I’d like to share some proven methods and tips for shopping in the sales that I’ve learned over my many years as a personal stylist.
These tips will help you avoid the mistakes that many of my styling clients have made when shopping in the sales.
When’s the best time to shop for a sale?
When do sales happen?
This may surprise you, but you can predict when a brand will go on sale!
Retailers work according to a calendar. When the next season’s clothing arrives, they need to sell off last season’s stock.
For most brands, you can expect sales to start at the following times:
- For spring/summer sales: late July/August
- For fall/winter sales: mid-December/January
This means you can prepare during these months and keep an eye out for your favorite brands if you want to grab a bargain!
My tip: Sign up for a brand’s newsletter and follow them on social media. That way, you’ll usually be the first to know about sales.
When a brand sends you an email about their big seasonal sale, mark the date in your calendar so you can look for patterns in the future.
When’s the best time to shop a sale?
A general rule of thumb: the later you shop in the sale, the more you save, but the less choice you have.
This makes sense, because early shoppers who don’t mind saving a little less have first pick of items and sizes.
I like to shop early in the sale to get the best items, even if it means saving less.
Sale items are usually styles that didn’t sell well for some reason, or unusual sizes. Popular styles and sizes tend to sell out quickly.
If you’re very short or very tall, or looking for something special, it’s usually worth waiting for further discounts!
A Personal Stylist Tips and Tricks for Shopping Sales
Remember that sale items are usually non-returnable!
It’s always better to pay 100% for something you love than 50% for something you hate.
Keep in mind that most stores have a “no exchange” policy on discounted items.
That’s why it helps to have a plan when buying special offers. Below are the rules I follow when buying special offers for a client.
1. Shop with a plan
It’s pretty advanced to casually browse a sale rack or sale section and pick out great bargains! Even I find myself pulling out items that I’m not sure about.
For the average man, I always recommend shopping with a plan to avoid impulse purchases.
Here’s how you can do that.
Take inventory of your closet.
What are you still missing? What important pieces of clothing might you be lacking? Make a list.
You may find that you haven’t bought light blue jeans because they didn’t fit into your budget. Maybe you put off buying a navy blue suit because it was the middle of summer and a suit on sale would be a bargain.
If you’re not sure what you might be missing, read my post on capsule wardrobes or my course on building one.
Double up on essential basics
You can always buy two or three of your essential basics during the sales.
Some essential items I like to buy during the sales are plain and striped shirts, ties, chinos, and shorts.
Use website filters to narrow down your list
Online stores usually have filters that make it easier to find what you’re looking for.
I recommend going through your list and setting the filters to show only items on your list to avoid impulse purchases.
2. Only buy sale items in your size
It amazes me when my clients tell me they bought something that is 1-2 sizes too big just because it was 30% off.
Never forget the most important rule of style: make sure your clothes fit.
How about having something tailor-made?
Yes, that’s an option, but consider the opportunity cost.
Do you really want to take a pile of clothes to the tailor? How much time will that take out of your busy schedule?
Alterations at the tailor are like cosmetic surgery: less is more.
If you start cutting things up and making them 1-2 sizes smaller, you’ll end up paying a lot and negating the savings you were trying to achieve.
3. Never buy something just because it’s a good deal
The golden rule: If I wouldn’t buy it at full price if I had the money, I won’t buy it on sale either.
4.Consider the season
Don’t forget that clothing is seasonal.
T-shirts you buy in the summer are thinner than T-shirts you find in stores in the fall. Chinos you find in November are thicker and sometimes lined to protect you from the cold.
If you shop at the end of the season during the clearance sale, you may not be able to wear the clothes for long and will probably have to pack them away for next year.
This is less of a problem if you live in a city where the weather doesn’t change much between seasons.
However, if you live in a city like New York, where there are distinct seasons, you should consider this before buying a thick winter shirt in the February sales.
5. Don’t buy to flip
Every season, auction sites are flooded with designer clothing from obvious hoarders.
I often browse these sites, and most of these items are still online years after they were first listed.
To be blunt, selling designer fashion is difficult. And the market for men’s fashion is small.
Unless you’re an expert in men’s clothing and selling clothes is your full-time job (in which case, why are you reading The Essential Man?), you shouldn’t buy clothes on sale to resell them for a few dollars profit.
It’s simply not worth the effort.
My favorite stores to shop sales
Ok, so now you know how to approach shopping sales. Where should you go shopping at the end of the season?
Here are some of my personal favorite shops!
Mr. Porter

Undoubtedly the best online store for men. A great mix of casual brands such as Polo Ralph Lauren and Nike to high-end designers such as YSL and Brunello Cucinelli. The modern man will find everything he needs here. With over 500 brands, the end-of-season sale can be overwhelming, so I highly recommend starting with a list. I’ve picked up some great cashmere items, jeans, and shoes here in the past.
