$4000+ Summer Outfit for Under $300: Techniques for Online Menswear Shopping

Looking good and having nice custom-made suits and bespoke shoes when you have a lot of money is relatively easy. On the other hand, if you’re on a really tight budget, it can be a lot harder–or at least, that’s the common perception! In an effort to debunk it, here’s how I was able to purchase an outfit online for over 90% off.

In Part 1 of this series, I already shared with you all the tips and tricks I’ve learned since 1999 on how to get men’s clothing on a budget. Here, I take the theory, turn it into practice, and show you that I actually got a summer outfit for more than 90% off of its retail price. Honestly, you can do it, too, and I’ll prove it to you by showing three different combinations that evolved around one jacket.

Growing up, I didn’t have a lot of money, so I had to learn to make my dollar or my euro go further. I started using eBay 1999 when I was fourteen years old and I quickly learned the ins and outs of it. In this second part of our series on how to buy quality menswear online for less, I’ll show you how I put together an outfit that retails for $4,315 and I just paid $255 for it. I’ll also show you how you can do it on your own, so you end up with something at a very steep discount. 

My $4000+ Summer Outfit for Under $300

Summer is here, and while you can get better deals buying winter clothes during the summer season and vice versa, I decided to get a summer outfit during summer to show that this concept even holds true when it’s a little more expensive.

The Jacket

When you buy an outfit, you should always start with a jacket or a suit, because that’s the most expensive item and the most difficult one to get to fit right.

First, I looked on Facebook Marketplace, on Poshmark, and on Etsy, and then finally on eBay; and eBay had by far the best selection. Armed with the knowledge of all of my measurements, I looked for a jacket in a 42 or a 44. I also knew that I wanted something that was summery, ideally with patch pockets to underline the casual character of the jacket. I wasn’t really interested in a suit, and went for a combination. All the principles outlined in part one work just as well with a suit, though.

So after going through many listings, doing some searching, and comparing measurements, I narrowed it down to two jackets that ironically even came from the same vendor.

One was a light gray pinpoint jacket from Borrelli (an Italian brand) and it had three nice patch pockets, a three-roll two style with notch lapels and side vents. The fabric was a wool–cashmere blend which is usually pretty soft. A jacket from Borrelli retails around €1200 which is about $1,300. The eBay list price was $119.99. The photos looked good, the jacket looked clean, there was no damage, and the description confirmed that.

The next jacket that seemed a good fit was from Isaia which is also an Italian brand from Naples. Today, they’re mainly known for their “Red Line” and their smart marketing with a piece of coral, which is commonly found in Naples, as their lapel pin decoration. Isaia also has a budget line called Gian Luca Napoli and so a lot of people get it confused but I knew that before they had the Red Label their mainline was the Gianluca Isaia Napoli so I knew quality-wise, this was the same level as the highly regarded Red Line. That’s one of the reasons it’s so important to build your knowledge about brands if you want to find good deals online.

I think Isaia switched to the Red Line labels in around 2006, so I knew the jacket was about 15 years old. Some people may be put off by wearing clothes that are 15 to 20 years old, but if the garment is hardly worn, and has been stored properly, you always get a very clean, timeless classic men’s style. So, onlookers would never be able to tell whether a jacket is 2 years old or 20 years old.

Even if I had not known about the details of the brand, I could recognize the finely sewn handmade buttonholes with a silk thread and assumed that it’s a quality jacket just because of that, because it’s not something you’ll find on inexpensive jackets. And typically, if they put a lot of time and effort into the buttonholes, they do the same with the rest of the jacket. The original list price on eBay was $139.99. Again, it seemed to be in great condition, it had this beautiful pastel color which I liked.

Putting The Items In A Watch List

I watched both of the jackets–the Borrelli and the Isaia. Both of these listings weren’t the traditional auction but a “buy it now.” When I watched it, I got an offer from the seller for both jackets that were below the list price. Now I knew he was motivated to sell, so I sent him a message asking if he would give me both of the jackets shipped for $150 if I bought them together. after all, that would save him on shipping and he gets rid of something. He agreed to that.

Both jackets arrived just stuffed in one “priority mail” package but when they came out they had hardly any wrinkles. Generally, that’s a sign of a nice fabric unless of course, you get maybe a linen garment. Sadly, the Borelli jacket actually had a little stain in between the buttons (which wasn’t visible in the pictures or mentioned in the description). So, I reached out to the seller and he offered a $10 refund, but that’s usually not enough to go to the dry cleaners. Even if I were to agree to that, I wouldn’t know if the stain would come out, because it may have been set in the garment for a decade or longer and you just don’t know. He also offered, of course, to take it back because it was their fault, and so I agreed to send it back to them for a full refund.

Even though both listings had the same measurements, the jacket fit differently. I felt that the gray one was a bit longer and also wider in the shoulders. The green one fits me much better. So keep in mind, just because someone provides measurements doesn’t mean they’re 100% accurate; trying a garment on and seeing how it works for you is the best way to determine if it’s right for you. At the same time, the measurements really help you to dial things in so you don’t end up with stuff you just have to return.

Right out of the box, I could see it was nice handwork underneath the collar and even a sleeve had a typical Neapolitan, kind of waterfall sleeve-head or sleeve wrinkles. The fit of the green Isaia jacket was really nice. It had high armholes, there was a good range of movement. It felt extremely comfortable and it looked quite good out of the box without any alterations, except for the sleeves because they’re on the shorter side (but I knew that, because typically my sleeves are about 25.5 inches long or 26 inches). This one was listed as only being 25 but I knew that I could let it out because it was in good condition.

Also with higher-end jackets, they are usually more fabric reserves so I could maybe try to have the sleeve lengthened from the top but you need a very skilled alterations tailor to do that, and it’s typically also more expensive. If I just let the sleeve out at the bottom, it’ll probably cost me around $50 in the alterations tailor. Normally, I wear garments for a little bit just to figure out if I want to let it out by how much, but for this jacket, I’m pretty sure I’m going to do it.

The Pants

Once I had my jacket and I knew what it looked like, I could continue with the pants. First, I picked up a pair of Polo Ralph Lauren seersucker pants because they’re very lightweight and summery at $30. I found one that didn’t come in a typical blue and white color, but in a beige and white color. I figure it would look quite nice with the green jacket, and create that summery feel I was going for.

Of course, I wanted to show you some different outfits so you don’t think this was just a one-off thing but I truly believe that you can repeat this process and get the same results. So, I got a second pair of pants in a brownish cavalry twill which is a little heavier than the seersucker, but still appropriate for summer. Lastly, I got a pair of glen check pants in a cotton fabric, which is rather unusual, also in kind of a brown tone.

Both of those were vintage Polo Ralph Lauren. One of them came even new with tags. They retailed for $125, but the cavalry twill one cost me $37.50, and the other one only cost me $17.99–shipped. I say that because sometimes a listing can be $5 but then the shipping costs $23. So, at the end of the day, what matters is the full amount you pay. 

The Shirt

Now that I had a jacket and pants that would work well, I could select the right shirt. In the process, I bought a bunch of different shirts because in this series, I want to do a separate piece on shirts alone and what you should look for, so stay tuned for parts 3 and 4!

For the seersucker pants, I wanted a casual look. Maybe something in linen or maybe a denim shirt. Generally, I think finding pants and jackets that are very gently used, pre-worn is relatively easy. When it comes to shirts though, a lot of pre-worn shirts are worn heavily and sometimes completely worn out. Some may have nice brand names and people put them on eBay thinking someone is going to pick them up because of that. But even if you have a shirt that retails for $1,000, if it’s worn out or if you get it at just $20 or $10 and you can’t wear it, it’s worthless. So, looking very closely at pictures in the largest version possible is key for shirts.

Typically, a shirt wears out at the shirt cuff. If you have a barrel cuff, it’s usually at the edges first, if you have a double cuff or french cuff, it usually starts to wear at the crease on the cuff where you fold it. Also, you can look at the tip of the collar because that’s where it typically wears fast, or at the upper edge of the collar where it wears second. Of course, if you see stains in the armpit area or around the collar, you’ll know that the shirt has been worn a lot and it’s probably not something you want to invest your money in.

For example, I bought a nice looking striped shirt from Borrelli which retails for about $300, has a lot of handwork, the fabrics are really nice and it was advertised as being in great condition without any visible flaws. When I got the shirt, the collar tips were already worn and so were the edges of the sleeve cuffs. I knew the shirt was almost at the end of its life, so I returned it.

For this outfit, I found a denim shirt from Eton which retails for $195. One thing I like about Eton is that they have longer sleeves, and I have longer arms so it typically works for me. Their slim fit is very attractive; it’s not boxy but it’s also not super slim so it works for me.

In their Red Line, they also have nice fabrics and help them treat them with an anti-iron coating that is much better than other stuff you can find in the industry. They don’t have much handwork, but the buttons are sewn with Ascolite, so I know they’ll never come off. Overall, the fabrics are of very good quality. At the same time, it’s not a brand that everyone knows so the listing price on eBay was just $25 for a shirt that was in pretty good shape. I made an offer and got it for $20, shipped.

Because it has a casual button-down collar and overall it’s a very casual combination, I decided to skip a tie for this outfit–but I wanted a pocket square and I added one from eBay which cost $15. It’s no name but it worked color-wise with a shirt and a jacket

The Shoes

Next up, I needed shoes. You can find tons of high-end brand shoes, like Allen Edmonds, on eBay. I wanted something in the lighter brown or tan range that would work with a summery outfit. I found a pair of Meermin in cognac tan, and it’s a brand that is in general relatively inexpensive for the value and quality you get. You’re not necessarily going to get huge savings, but it’s still a good brand and still a good shoe, and you have to kind of see what’s available at any given point in time.

The shoes I got retail for $195, and they were in an auction format. I won the auction for $56 but with the shipping, it came to $70.32. The funny thing was when I got the shoes, the seller added a note and said “Thank you very much for all the videos. I really appreciate the Gentleman’s Gazette.” I appreciate it, of course!

I like the color of the shoes. I was wondering if I could make them even nicer and so I sent them over to my friend Preston Soto from The Elegant Oxford to give them a nice shine and look. When they come back, we’ll give them away to one lucky winner. They’re a size 10 UK on the HIRO last. So, stay tuned for the giveaway!

The Belt

For the belt, the cognac tan one from the Fort Belvedere belt system would have worked really well but it’s a little more expensive because it’s really high quality and you can exchange everything. So for the purposes of this post, it wasn’t a good fit. I looked around to hopefully find something that was roughly in the same color which can be difficult, because the photos are sometimes shot with different white balances–so even though they may look the same in the pictures, they may actually not look the same when you get them. But in general, I just wanted something that was close enough, so I got a belt from Polo Ralph Lauren for $30, which retails for $75.

Nothing special but it does the job. I’m a size 36 belt. If you’re smaller like 30 or 28, you’re going to find tons of belts, sometimes even alligator for $30, which is really incredible.

The Socks

For the socks, I bought a pair of new Falke socks, which is a German brand. I got them for $15 and they retail for about $20 or $25. They have some polyester and they’re not as nice as my Fort Belvedere socks, but I truly wanted to put together an outfit that was very affordable and that had no Fort Belvedere items in it.

How Much Did The Whole Outfit Cost?

Alright, now have you seen the first outfit, let’s go through the retail price breakdown and how much I paid for it. 

• The Isaia jacket was $3695;
• The seersucker pants had a retail price of $120;
• The Eton denim shirt retailed for $195;
• The Meermin shoes retailed at $195;
• The pocket square, I just left at $15 because I didn’t get the exact price;
• The belt was $75; and
• The socks being $20.

That gives us a total of $4,315 retail value.

So what did I pay?

• $75 for Isaia jacket;
• $30 for the Ralph Lauren pants;
• $20 for the shirt;
• $15 for the pocket square;
• $70.32 for the shoes;
• The belt was $30; and 
• The socks $15.

So, that adds up to $255.32 That’s the equivalent of 94% off! Even if I account for the $50 in alterations costs, I go up to $305.32 which is still 93% off!

Again, this wasn’t pure luck but it’s the result of a process. Because of that, I used the same jacket but made some changes for the other items to show you that it’s actually true.

Outfit # 2

• I changed up the seersucker trousers for the cavalry twill. The retail was $125, I got them for $37.50.
• Instead of a denim Eton shirt, I got a white Eton shirt for $20, which also retailed for $195.
• The tie I bought for $5, shipped from eBay and it’s a nice blue and yellow stripe tie, very thin in a kind of summery fabric. It came from a brand called Personality Milano which I’m not familiar with, but probably retailed around $20.
• For a pocket square, I could have picked a white linen one on eBay, but I already have really nice ones from Fort Belvedere, especially with the hand-embroidered initial and hand-rolled edges, so I just used that. The retail prices are at $65.
• When it comes to socks, I’m a big fan of two-tone socks because they’re so easy to combine. I picked a pair of Fort Belvedere socks in navy and yellow which picks up the colors of the tie and it retails for $40. Of course, you could have also found a new pair of socks, maybe striped or otherwise on eBay for less.

The total retail value of this outfit is $4,410. I paid $342.82 for it and that includes the Fort Belvedere items at retail price. Still, that’s 92% off the retail price! If I account for alterations (shortening the hem of the pants for $15 and the sleeves of the jacket for $50), it is still a great deal.

Outfit #3

For the third outfit, I wanted to incorporate more patterns. So I chose:

• A pair of pants in a glen check pattern which was brown and light brown which I thought worked really well with the jacket. Retail price $125, I got it for $17.99 because it was used. It was described as a herringbone pattern (which is not true), but I looked at it, liked it, and got a deal.
• The shirt I picked up is from Luciano Barbera which is not a really well-known brand but Mr. Barbara is a really good dresser and has an impeccable sense of style, which is also reflected in his clothes. While their shirts don’t have the same level of handwork detail as a Borrelli or Eton, it’s still a high-quality shirt that uses very nice fabrics. They also have little details, for example, the sleeve folds, which should help you give more movement with a smaller armhole. The fabric is really nice. It has green and white stripes with elements of blue, with a hint of purple.

• For the tie, I chose a green linen one with a really oversized polka dot in white which is very summery. It retailed for $125, I bought it on eBay for $5. You can tell it’s an older tie because it’s much wider, about 3.5 inches.
• For the pocket square, I went with a no-name linen one that had really small dots and a contrast edge in beige that would pick up the color of the pants but also the polka dots of the tie, and thus, tie everything together. Also, the dots in the pocket square are a lot smaller than the dots on the tie, so it works harmoniously together even though they are all different patterns.
• For the socks, again, I went with a pair of two-tone socks in brown and green which tied everything beautifully together with the shoes and the pants. 

So if you add up the retail value for this outfit, you get about $4560; I paid $266.29 and if you add $50 for the alterations, it’s $316.29. Again, huge savings–way over 90%!

Are The Savings Worth The Time?

Naturally, it sounds great to get such a big discount but you always have to be honest with yourself and ask, “How much time did it take me to put together this outfit?” and “How much could I have earned during this time?” or “What would have been the spare time worth to me if I hadn’t served for that stuff?” The math is different for everyone, of course, because some people earn more, others like shopping, others hate it, so it’s something that you have to come up with and add it to the overall cost.

For me, it took me about 12 hours from start to finish, including the returns of the items, searching for things, comparing them, communicating with the sellers, getting them, and so forth. So, that’s a not-insignificant amount of time, in my mind. Nevertheless, if you’re on a very tight budget and you can invest a little bit of time, you can get great results and huge discounts.

Did you enjoy this outfit assembly post format? I could do another one like this for other types of outfits. Let us know in the comments!