men's clothing store

5 tips for shopping sales from a personal stylist

By: Peter Nguyen
Last Updated: August 6, 2021

So you’re getting tons of emails from brands about their end-of-season sales. 

Who doesn’t love a good deal?

It can be tempting to pull the trigger on a jacket you’ve been eyeing that’s now 50% off. But mindlessly shopping sales can get you in trouble. 

I’ve seen clients waste thousands of dollars on clothes that don’t fit their bodies (or, frankly, are ugly), simply because they were on sale!

The point of a sale is to save money! Not end with a pile of unworn stuff you got because it seemed like a deal at the time.

I want to share some best practices and tips I’ve learned over the years at a Private Personal Stylist on shopping sales. 

These tips will help you avoid the past mistakes many of my styling clients made shopping sales.

When’s the best time to shop for a sale?

When do sales happen? 

This might surprise you, but you can predict when a brand is going to go on sale! 

Retailers operate on a calendar. As the next season’s clothes start coming in, they need to clear out the previous season’s stock. 

For most brands, you can expect sales to start in these times:

  • For Spring/Summer sale: End of July/August
  • For Fall/Winter sales: Mid December/Jan

That means you can start preparing and keeping an eye out for your favorite brands around these months if you want to score a good deal!

My tip: Sign up for a brand’s newsletter and follow them on social media. You’ll usually get a heads up on sales before people catch on. 

When a brand emails you about their big, end-of-season sale, add it to your calendar so you can start looking for patterns in the future.

When’s the best time to shop a sale?

A general rule of thumb: the later in the sale you shop, the more you’ll save, but the fewer options you have to pick from.

Which makes sense, as early shoppers who don’t mind saving a bit less will get first dibs items and sizes. 

I like to shop early in a sale to get prime picks, even if it means sacrificing savings. 

Sale items are usually styles that didn’t catch on for whatever reason or odd sizes. You’ll usually find popular styles and sizes go. 

If you’re extremely small or extremely large or are looking for something a bit unique, it’s usually worth it to wait for further markdowns!

A Personal Stylist Tips and Tricks for Shopping Sales

Remember, sale items are usually final!

Paying 100% for something you love will always trump paying 50% for something you hate. 

Remember that most stores have an “all sales are final” policy when it comes to markdowns. 

That’s why it helps to shop sales with a plan. Below are the rules I follow when shopping sales for a client. 

1. Shop with a plan

Browsing a sale rack or section casually and picking out great deals is quite advanced! Even I find myself pulling items I’m unsure about. 

For the average guy, I always recommend shopping with a plan to avoid impulse purchases. 

Here’s how you can do it.

Take inventory of your closet 

What are your gaps? What are key pieces you might be missing? Make a list. 

Maybe you realize you didn’t pick up light blue jeans because it wasn’t in your budget. Maybe you held off on buying a navy suit since it was the middle of summer, and a suit on sale would be a great buy.

If you’re unsure of what you might be missing, check out my post on capsule wardrobes or my course on building one.

Double up on essential basics

Essential basics are always great to double or triple up on during sale season. 

Some essential items I love shopping for during sales: solid and striped button-down shirts, ties, chinos, and shorts. 

Use website filters to hone in on what’s on your list

Online stores will usually have filters to help you find what you need. 

I recommend going through your list and adjusting the filters only to show you items on your list to avoid impulse shopping.

2. Only buy sale items in your size

It blows my mind when my clients tell me they bought something 1-2 sizes too big for them just because it was 30% off.

Never forget the #1 style rule: make sure your clothes fit. 

What about getting something tailored?

Yes, that’s an option, but consider the opportunity costs. 

Do you really want to bring a stack of clothes to the tailor? How much time will that take out of your busy schedule?

Tailoring alternations are like plastic surgery; less is more. 

When you start chopping things up and going 1-2 sizes down, you end up paying a lot and negating the savings you were after. 

3. Never buy something just because it’s a good deal

The golden rule: If I wouldn’t buy it full price if I had the money, don’t buy it on sale. 

4. Keep the season in mind

Don’t forget that clothes are designed to be seasonal.

T-shirts you pick up in summer are thinner than a t-shirt you find in stores in the fall. Chinos you come across in November will be thicker and sometimes lined to help fight off the cold.

When you’re shopping end of seasons sales, you might not be able to wear the clothes for much, and will prob have to tuck it away for next year. 

This is less of an issue if you live in a city where the weather doesn’t change much between seasons. 

But if you’re in a place like New York City like me with distinct seasons, keep it in mind before you pick up that winter weight shirt on sale in Feb. 

5. Don’t buy to flip

Every season you see a flood of designer clothes on auction sites from obvious sale hoarders. 

I skim these sites often, and so much of this stuff is still up years after their initial listing. 

To be blunt: selling designer goods is hard. And the market for men’s stuff is small. 

Unless you’re a men’s clothing expert and it’s a full-time job to flip clothes (in that case, why are you even reading The Essential Man?), don’t buy clothes on sale with the intent of flipping it for a few extra bucks. 

The juice isn’t worth the squeeze.

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 online men's store
Mr. Porter’s online store

Mr. Porter

Hands down, the best online shop for men. A great mix of casual brands like Polo Ralph Lauren and Nike, to high-end designers like YSL and Brunello Cucinelli. The modern man can find everything he needs here. With over 500 brands, the end of season sales can get overwhelming, so I highly recommend starting with your list. I’ve scored some great cashmere, denim, and shoes here in the past. 

Bonobo's online men's store
Bonobo’s Online Store


Bonobos is what I consider my new “J.Crew.” A no-bs shop where you can get staples like chinos, button-downs, and tees in the exact size/cut you need every season. If you want to save money on some office essentials, this is the place to go. 

Todd Snyder online men's store
Todd Snyder’s online store

Todd Snyder

Todd Snyder is like Bonobo’s cooler older brother. A bit more like J.Crew (Considering Todd Snyder did work at J.Crew) You’ll find a lot of wardrobe staples like bomber jackets, sweaters, and jeans, but a bit trendier and, dare I say, cooler. Todd’s end of season sales are excellent. I’ve scored some great sweaters and even a suede jacket on sale for my styling clients. 

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