How to Get 80% Off Menswear Every Time: My Secret Step-By-Step Process

Most people assume that in order to look good and dress well, you need a lot of money, but that’s not necessarily true! Of course, if you’re wealthy, it’s much easier to put together a nice, bespoke wardrobe and look the part. However, there is also a way to do so on a very tight budget–and I’ll share how today!

Shop Menswear for 80% Off The Price Tag

Honestly, you can look and feel like a million bucks without spending too much. Don’t believe me? I’ll prove it to you. In part two of this series, I’ll put together an outfit from scratch that retails for more than $3,000 while only paying under $300. The best part is, I don’t even have to step a foot outside my door to do it; I can do it all online. I’ve been shopping online for menswear since 1999 and today, I’m going to share all my secrets, step-by-step with you, so you can also get at least 80% off every time you buy menswear.

1. Know Your Measurements

Without measurements, even a $10,000 garment looks crappy on you, and that’s not the point. The reason we want to dress up and have nice garments is so we look good, and fit is of utmost importance. You might say, “Well, do I really need the measurements? Can’t I just return things, because I already know I’m a size Large or 42 regular?” Of course you can, but shipping things back costs money and frankly, it’s a huge pain to go to the post office or to UPS and return stuff.

Unlike with a bespoke tailor where you look for body measurements, you here want to look for garment measurements. So ideally, you’ll already have one perfectly fitting garment like a jacket so you know what you’re looking for, and then you can punch in those numbers online and make sure you find something that works for you.

If you’re just starting out and you have no garments, the key is to get proper body measurements, then add a little bit to them and try to find a garment that fits you well. Once you have that, you can refine your garment measurements.

Why is it so important? Every manufacturer has a different sizing system, and what’s regular in one brand may be a whole lot smaller or bigger than that of another brand. Sure, you could just walk into a retail store, try on all their sizes and then go back home and shop online, but that wouldn’t be fair for the retailer. So instead, you can just take your body measurements, estimate your garment measurements, buy something, try it, and then you will see what you’ll need. For example, if the sleeve is too short by an inch, then you can just add that on and you have your garment measurements.

Over the years, I’ve found these measurements are the most important things.

Jackets

The four key measurements you need for a jacket are:

1. Your chest measurements (armpit to armpit laid flat)
2. The shoulder width, measured from shoulder seam to shoulder seam in the back
3. The sleeve length, measured from the top of the sleeve to the bottom of the hem around in the middle
4. The length of the jacket, measured from the base of the collar from the seam all the way down to the hem in the middle

I would say that most vendors on eBay and other platforms adhere to those four measurements. Sometimes though, if they’re amateurish they’ll maybe measure the sleeve length from the armpit, or the entire back length including the collar; so it pays to really read the description carefully so you ensure that the measurements that you have for your garments are actually measured in the same way.

Trousers

For pants or slacks, it’s even easier, because you just need the inseam measurement and a waist measurement. Of course, if you have big thighs like me, you want to ask for a thigh measurement or make sure that you’re not buying slim-fitting pants.

Shirts

The most important measurements for shirts are the collar size and the sleeve length, which is traditionally measured from the split yoke (or the center of the yoke) from the back to the end of the sleeve. Sometimes, they measure the sleeve length from the top of the shoulder seam. If that’s the case, you can also measure in the same way and then, in addition to that (just like with a jacket), get your shoulder-to-shoulder measurement. If you have a long torso like me, knowing the overall length of the shirt can also help, because if you have a shirt that always comes undone, it’s just uncomfortable to wear.

Shoes

When it comes to shoes, measurements are not really so important. Instead, you should simply know your size. Why? Well, a size in length, for example, will not tell you if the shoe fits, because the width is important in a specific last shape. Of course, different brands have slightly different sizes. Personally, I range between a US 11 or US 11.5 in most brands. However, with Allen Edmonds (depending on what lasts I use), I have a range from 10.5 to 11 and 11.5. Also, if you buy shoes from Europe, such as Italy or England, you may find a European sizing system which, for me, is typically 44.5 to 45 EU or around 10.5 UK.

With the popularity of online shopping for men’s shoes, I’ve even seen brands advertising that “if you have a Crockett & Jones in this size on that last, then get this size in our shoes” or, “if you have Edward Green in this size then get that size in our shoes.” That can be sometimes very helpful to understand; for example, “Hey, I have this pair of Crockett & Jones that fits me really well in this last and size, so in that brand, this will help me.” Places like online forums can oftentimes be very helpful in that regard, because there are a lot of people who have tried many different things.

Accessories

For accessories, measurements can be important, but for example, the length of your tie depends a bit on your height and your torso length as well as the rise of your pants, so unless you know exactly what outfit you want the tie for, it may not be very helpful. If you’re really tall, you should be looking for long ties; If you’re short, look for shorter ties.

In my experience, most sellers will not advertise the length of the tie, so if you want to know it, you have to specifically ask for it and if you really care about length your tie, you’ll probably have to buy something new such as the ties from Fort Belvedere which come in long, regular, and short. But even though I design my own ties and we sell our own brand, I still buy ties on eBay sometimes because I like the different patterns; I like vintage ties, and it’s just fun to see how different fabrics were designed, how they feel, and how they tie up so I can learn something for our ties.

2. Buy Gently Used Garments

The key is that you buy gently used pre-worn garments or garments that are new with tags or without tags from market places such as Facebook Marketplace, Etsy, eBay, or Poshmark. Of course, as with anything vintage or pre-owned, there are various levels of used or pre-worn. Sometimes, items have been worn once or not at all, and they’re in pristine condition. Other times, you’ll find shirts with lots of wear on them; even like collars that are stained or jackets with rips holes, and stains.

Personally, I always prefer to buy something that has a lot of wear left in it and it doesn’t have any visible defects. Sure, if there’s a little stain on the lining on the inside or a loose thread that I can fix, well that’s a great way to get a bargain. On the other hand, if something is visible on the outside, you don’t know if a dry cleaner can actually get it out and mending is expensive, too.

3. Brainstorm Your Outfit

So how do you get an outfit that actually looks good and not something that is really cheap and 80% or 90% off? Well, you have to brainstorm your outfit. I know it can be very tempting to just buy the stuff that has the biggest discount. Reality is, sometimes, those huge discounts especially for new items are there because the item is very special and it’s very difficult to combine and you get very little wear out of it.

Think About Your Specific Needs

Do you need an outfit for an interview? Then you get a dark suit with a white shirt and a tie; or do you want something lively that you can wear to a garden party? Then maybe you get a louder sport coat with a pair of chinos and a patterned shirt. You can even go so far to say, I want a single-breasted 2-button suit with brown shoes and a light blue shirt.

If you go any more detail than that, the problem will be that it’s going to be very hard to find a larger range of items that you can look at–because, at any given point in time, there’s only so much on the market. For example, if you truly want a navy sharkskin suit with brown horn buttons and a ticket pocket, chances are, you have to wait a lot longer and you will even then not find exactly the item you want as used.

So as with many things in life, you have to find a balance and settle somewhere in the middle. Don’t be too wide and just search for a “dark suit” but also don’t be too specific instead search for something like a “dark suit with notched lapel” or “dark brown derby or oxford shoes” and you will find plenty of items. Honestly, it’s really important that you sit down and think about what you want, otherwise, eBay and all these marketplaces can be like a black hole where you’ll just be wasting money going through thousands and thousands of listings and your time is worth something, too.

4. Search For Garments In A Smart Order

Once you know your garment measurements and sizes and you know exactly what the type of outfit you want, I suggest you start searching for the jacket first, then the pants, the shirt, and then the accessories. So why do I search in that order? Well, to get the fit right for a jacket is more difficult than with a dress shirt, for example, or a tie and even pants. Also, jackets generally come in more different patterns, sizes, and they often have more details and they’re typically also more expensive, so I want to give myself the largest possible room to find something that I truly like and it fits.

At any given point in time, they’re probably also more shirts and specifically pants on the market and jackets, so if I’m not in the market for a suit, I choose the pants second so I know it really harmonizes well with a jacket because they can be the greatest trousers in the world but if they clash with my jacket, it’s not going to work for my outfit. Only after the jacket and pants should you add the shirt, because you can find all kinds of solid shirts or patterned shirts, and you just want to make sure that if you have different patterns and colors, they won’t conflict with one another. Finally, if you have those three pieces together, you can add some accessories to taste.

My Steps To Getting Great Menswear Deals

Now that we have those guidelines out of the way, let’s go to the actual search. Generally, your query should be in the right range between too vague and too specific. For example, I’m typically a 42 regular in most jackets, so I start searching for “41, 42, 43, and 44,” because I know with some Italian brands to typically run small and I need a 44 regular there. A lot of times, people have a very different understanding of what a short jacket or a long jacket or a regular means, so I typically drop the regular and just search for “41, 42, 43, and 44.” Keep in mind not everyone is an expert and the measurements are sometimes also slightly wrong, so I just want to be in the right range.

1. Prepare Questions To Ask The Seller

Sometimes, you might also encounter sellers that don’t share measurements. They just say, “Oh, it’s 42 regular or it’s size L.” Well, that’s not really helpful–but this can work in your favor because you can ask the seller what the measurements are. Typically, they will share them with you but they won’t even put them on the listing, which means there’s less competition for you. I maintain a Google document with canned questions,  including the one shown below. That way, I can make sure that they’re measuring exactly in the same way that I measured my own garments.

If a listing does provide measurements, compare it to your own and sometimes also keep in mind that measurement to a quarter inch is not that accurate because a fabric is typically flexible and you don’t know if they measure it when it was lying flat, which is what they should have done if the button was buttoned or not, and so there’s always a little bit of variation that you have to keep in mind.

2. Use The Online Platform’s Functions

Certain platforms allow you to filter also for sleeve length. Facebook Marketplace, for example, doesn’t have much for that. Poshmark, also not so much but on eBay, there are more functions so you can look for sleeve length or the length, which makes things easier especially if there are thousands of items. Personally, I find for classic menswear that eBay is best because of the best prices but also the best and largest selection.

3. Go To A Specific Category

On eBay, a great way to narrow down your search to only the things you truly want is to first go to the right category of things you’re interested in, then you can add additional filters on the side such as color or a specific size, and that’s a good way to search for it. Typically, I start my search by going to the right category and then just searching, for example, for 42 Purple Label because it’s a brand Ralph Lauren Purple Label for example and I know that it’s a good brand and know that it’s something I’ve bought in the past and I know what size I have in that brand.

Once I get a limited amount of listings, I scroll through and see what I like and I use a tool called Linkclump that allows me to quickly open many links in one go. At this time, I’m not even looking at the listing or just opening up the links in new tabs then later on I can compare every product one by one next to each other in quick succession.

When it comes to pants, I typically only search for the waist size, because there are many inseam lengths. Some better pants especially if they’re newer are unhemmed, but it’s also very easy to make a pair of pants shorter, so oftentimes you can get really great deals on pants that are let’s say, “36-35” or “36-34” because there are so many people out there with legs that long.

Also, if you have a 32-inch inseam and you find a pair of pants with cuffs and a 31 inseam, you could let them out so keep that in mind. Alteration for something that typically costs anywhere between $12 to $20, depending on where you live in the US. Personally, I like cuffs, so I always prefer to have pants shortened rather than lengthened because with the lengthening, sometimes there can be an issue if the pants have been worn at the edge and when you let it out you see that the fabric has been worn in one particular area.

4. Narrow Down Your Search

If I find that there’s too much stuff in a category or see a lot of listings from new things that I don’t like, I select pre-owned only and may be at a color. Remember, not every seller describes their item perfectly. Sometimes, they just have a picture and the measurements and that’s it.

5. Search For A Brand

So in the first place, you want to cast a very wide net and that means that you can also search for misspelled brand names. For example, looking for a shirt, there is an Italian brand Borrelli which makes great shirts but if you misspell it with just one R, you fly under the radar and that’s something where you can really score a bargain. Same with Allen Edmonds; it has an O but sometimes people think it’s Edmunds.

You also don’t have to search for the entire brand name but just parts of it. Rather than looking for Ralph Lauren Purple Label, you can just search for Purple Label because there are not that many suits that have the description “Purple” and “Label” in it. Also, you can search for variations such as “RLPL.”

6. Set a Budget Range

If you’re on a strict budget, you can also limit the search results by how much you’re willing to spend but keep in mind that oftentimes, you can make offers on expensive stuff that is 30% or 50% off the listing price of eBay. So let’s say, your budget is $200 and you set a limit, there may be a jacket listed for $220 you could actually buy for $120 but you’re not even seeing it because you’ve excluded it with a filter.

7. Open Items In Different Tabs

Typically, I find around 20 items that I can then compare. If you open more tabs in your browser and you don’t have a lot of memory, your whole browser might crash and you have to start all over, so keep that in mind. Personally, I have 64 gigabytes of RAM, so I can have actually 80 tabs open and it still all works. The advantage of looking at items tab by tab is that you can compare much more easily. If you know that you already liked it visually, now you just look at the measurements, if something doesn’t fit, you click it away. If you like something, keep it open and just go through.

That’s the first selection process then in a second one, you do it again. If you look at all the items that you liked that potentially fit you and double-check the measurements, double-check the photos very closely, so you can see if there is any damage because sometimes, people just take a photo of the damage but they don’t describe the damage. That way, you narrow down your choices more and more.

8. Have A Watch List

In the next step, I add the items to my watch list. Why do I do that? Well in the one hand, it gives me a nice overview on eBay to look at all the things that I liked that I thought would fit me and on top of that, the seller gets a notification that you’re watching something so I would say in about 30% of the cases, the seller will send out an offer that is below their asking price just for me. I find that if someone sends me an offer, that’s a great bargaining ground because I already know they’re motivated to sell so I can get maybe even a lower price that even works better for me.

Again, one of those reasons I urge you not to filter by price too much, because you may be missing out on stuff that you really like and you just think is out of your price range. Personally, I only ever buy at a listing price when a deal is so good that negotiating wouldn’t make sense. For example, if the shirt is just $10, negotiating and wasting time to get $2 off is not really worth it. On the other hand, if the jacket is $150 and I can get it for $75 that’s probably worth two minutes of my time.

9. Make An Offer

When you watch an item and you’re not getting an offer, in many cases you can also make an offer to the seller. Remember, always be friendly and kind because that way, they’re much more likely to give you a discount than if you’re rude. For example, many listings on eBay have a “make an offer” button and even if a seller doesn’t have that button, you can still reach out to them and say, “Hey, I’m really interested in this but my budget is X. Could you help me out here?” Even if they reply with a bit of pushback, this still shows you they’re motivated to sell, so maybe you can come in and even provide a more aggressive offer.

But again, always be nice, be kind, just explain to them that you’d love to have the item but you just can’t afford anything more. Don’t make them feel like you just want to squeeze them like a lemon. Almost all of them have a “make an offer” button, but they automatically set a limit at what they accept as an offer and at what limit should be declined. So, if you get a decline message right away, you know it was an auto-decline and you could just reach out to them and just see where they’re at because now, they may be in a different state than when they originally set the decline offering threshold.

Do’s and Don’ts of Shopping Discounted Garments Online

Now that you’re in the basics of how I search to get 80% off outfits from eBay, here are a few more do’s and don’ts that are very important and sometimes, a bit more advanced. 

DO: Search For As Few Brand Names As Possible

So, rather than looking for Ralph Lauren look for “Lauren.” Also, do a search for misspelled names.

DO: Search For Specific Sizes

If you’re size 11 and shoes search for “Edmonds 11” not “Allen Edmonds.” Yes, there is a size selector on the left bar, but do not just rely on that, because some sellers don’t know about the size selector, they don’t set their size, they just put it in the description and you would miss out on them if you don’t also use the description feature.

DO: Search On Your Desktop Browser

When you buy on eBay, search on your desktop browser, because it gives you the option to also search through the entire description in the advanced options which is not something you have on the app. Why is it so important? Well, if you can search the entire description, oftentimes, you can search for specific things like patch pockets or maybe a length or a size or they may not be enough space in a product tagline.

DO: Search For Specific Brands

Just looking at a category in menswear typically yields too many results.

DO: Search For A Specific Sub-brand

For example, I’m interested in Polo Ralph Lauren and in Purple Label Ralph Lauren. I’m not interested in Chaps or Green Label Ralph Lauren, so that means I would just search for “Lauren Polo 42,” if I was interested in a jacket or a suit or maybe “Lauren Purple 42.” By doing that, you don’t have to sift through all the stuff that you don’t want in the first place.

DO: Make Offers

Also, as I mentioned, make offers on items even though there may not be an “offer” button. You can even make offers on things like auctions that don’t have a “Buy It Now” price.

DO: Put Yourself In The Seller’s Shoes

Always think, “Well, they’d like to sell something and I’d like to get it off their hands. They’d like to deal with someone who is efficient and not mean.”

DO: Use A Sniper Tool

If you don’t participate in the bidding, definitely use a sniper tool. Why is that? Well, auctions end at a specific point in time and when you start bidding early, what can happen is someone who may only think that want to bid $50 on it may end up changing their mind and bidding $75 on it because they really, really want it and they have time to think about it. If you use a sniper tool, you can decide how much you’re willing to spend on an item without actually spending more than you originally intended to and you can just set it so it sends to bid three seconds before the auction ends so no one has time to react to your bid. That’s leading ultimately to a lower price for you.

DON’T: Use Long Search Phrases

I’d say, in general, avoid long search phrases unless you’re overwhelmed with search results, then you can try to get longer and longer at a time.

DO: Exclude Negative Keywords in Your Search

For example, on eBay adding a minus (-) or a dash directly in before a word excludes it from your search, and that can be really helpful if you see a lot of listings that don’t work for you. For example, if you’re looking for a jacket, you can exclude “quilted” or if you want to exclude a certain color or a country, you just add a minus before that word.

DO: Use A String Search To Narrow Down Your Results

Use quotes so it says, “Lauren Purple Label”, so it only shows you results where these words are exactly in that order.

DO: Sort and Filter Your Results

For example, if you’re on a budget you can say, “I want to display the cheapest item first, including shipping and I only want items that are yellow.” So, use the platform’s tool to sort and filter that out.

DO: Search For Materials

For example, if you know you want a summer jacket maybe add “linen” to your search string. If you want something for the winter, add “cashmere.” You may also want to search for just “pure cashmere” or “100% cashmere” for jackets, for example. That way, you know you get a more expensive item because, typically, 100% cashmere items are rather pricey.

DON’T: Buy Orphaned Suit Jackets

A lot of times on eBay, especially professional sellers, have single striped jackets in pinstripes and they’re simply orphan suit jackets and you can’t really wear them with anything else, so even though they may be really inexpensive and they may have a really high retail price, it’s a bad purchase because you can’t really wear it without looking stupid.

DO: Watch Items & Make Offers

I’ve already said before that you should watch items (in your watch list) and you should make offers but I just want to reiterate it because it’s so important.

DO: Visit A Seller’s Store

Last but not least, if you find an item from a seller that you like, check out their other items or visit their store because more often than not, I find that they may have items from the same person so you find a garment that fits you perfectly. They may have three others may be from different brands, maybe even better brands, smaller brands, less well-known brands, that you haven’t thought about, that you have found through the search but you already know it’s going to fit you based on the measurements of that one jacket.

On top of that, most sellers are willing to give you a discount if you buy more than one item from them because it saves money for them on shipping and logistics and it’s just easier for them, so they are happy to give you a discount.

BONUS 1: Have A List Of Quality Brands

I suggest you put together a list of quality brands because ideally, you want to search for brands that have very high quality but also a very good value ratio, and stay clear of items such as Louis Vuitton, Gucci, or Armani, because those things are so popular that they’re often faked–and even if they’re original, they’re often very expensive for what you get.

So to help you get started, I put together a list of brands for jackets and pants and shirts that I think are really good and that I would search for on eBay so that can get you a kick-start, and then you can add on things as you search and find new vendors and brands.

BONUS 2: Space Out The Time You Spend Searching

If you made it through here, that may all seem like there’s a lot to do and yes, you have to be persistent. And I urge you to check regularly for a limited amount of time rather than a lot of time in one day, so rather spend maybe half an hour or an hour once a week or once every two weeks than 8 hours on a Saturday. Why? Well, the offering constantly changes, and by looking longer in one day, you likely don’t magically find new stuff but two weeks down the line you may have 30% more or new items. Happy shopping!

Have you tried these techniques to score great menswear deals? Share your experience in the comments!

Outfit Rundown

I’m wearing of course, an outfit that consists mostly of stuff I bought on eBay. I was torn between two pairs of shoes, especially this one which I just recently bought. Now, I like the color but I think that can be even in better shape, so I asked my friend Preston Soto from The Elegant Oxford to actually polish them and he’ll do that, send it back to me and afterwards we’ll give them away to one of our followers. Alright Preston, ready for some shoes? Great, here you go!

My jacket is actually part of a suit and it was made by the bespoke tailor A. Caraceni in Milan and new cost thousands of Euros. It’s one of those unusual petrol blue fabric in a fresco wool, which is a very airy and great for summer. I think I’ve had about 70 euros for a suit which is about 85 bucks. The shirt is from Siniscalchi, which is a bespoke shirt maker in Milan and they usually retail at around 600 Euros or more. I got it for like 15 Euros because it was from the same owner as a suit and I knew that a person who would spend six thousand Euros or dollars on bespoke suits had likely more suits, which was the case and I got, I think, eight of them but also more shirts and ties which were of likewise high quality.

I’m combining with a pair of pants from Polo Ralph Lauren which is kind of a linen silk blend which is again, very airy and great for summer. It has a small houndstooth like pattern in black and off-white or beige it has pleats, is cuffed, and works with my big thighs which is something I appreciate from vintage Polo items which is why I go back and buy them.
My shoes are a pair of unusual monk strap shoes from Altan in Paris which he had custom patina for me. With a brown color, I’m wearing a brown belt from the Fort Belvedere belt system and I chose a silver buckle to go with my silver pinkie ring in sterling silver and tigers eye. It works well with my brown shoes as well as my tobacco brown knit tie from Fort Belvedere and to make it all work together, I chose a pocket square in brown and blue Paisley from Fort Belvedere which ties together the tie and the shoes.

The socks are also from Fort Belvedere they’re shadow stripe in grey and blue, which pick up the tone of blue in my shirt and gray in my pants and just tie it all together without being overly flashy.