Maybe you desperately need an upgrade, or you're noticing an area of sartorial deficiency. It could be time to replace something that fell apart or doesn’t fit. Whatever it is, it is going to mean going to a retail establishment (or pulling out your phone and browsing our shop while sitting on your couch) and spending your hard-earned cash.

There can be a little bit (or a lot bit) of sticker shock associated with making those purchases. Good clothes don’t come cheap. But I’m not here to tell you to downsize your apartment so you can buy only the finest Italian wool. I’m here for the opposite of that, because there are a lot of ways to navigate the murky canal of menswear and emerge without selling your car. But tighten the purse strings in the wrong area and you’ll be sorry.

So let’s talk about areas where you can save a few bucks and still look your best, and the areas where you shouldn’t dare skimp.

Where to Save

Denim

If you’re at all like me, jeans are "Sunday afternoon on the couch with a hoodie" through "Friday night at dinner with a blazer" and everywhere in between. So, it might seem counterintuitive to suggest denim as a place to cut back on spending. But hear me out.

In a world of unlimited funds, you could catch me wearing the world’s most carefully crafted denim. Nothing looks better or works in more situations than a classic pair of blue jeans. And high-quality denim is luxurious. It feels great, looks great, and lasts; this is the case for a big spend when it comes to denim.

But, the reality here is that we all have a budget. And if you’re choosing between super high-end, indigo-dyed, slub-woven Japanese denim (which are cool, but ain't cheap) and a suit or a pair of Oxfords, I say do yourself a favor and take the under on the denim.

This isn’t license to go cop the first pair of low-quality jeans you see. Don’t cheat yourself or you’ll wind up with a terrible pair of jeans, and consequently look and feel terrible most days of the week. But it’s possible to buy a great pair of jeans, that’ll last, in the mid-range that will look and feel great but won't have you short on rent for the month.

If you're a real denim obsessive then eventually, once there’s a little more room in the budget, you could upgrade to a really great pair. But there’s plenty of reason to keep some less expensive pairs in rotation, even then – daily drivers that look great, but that you can wear into the ground without stressing about. Read the labels, care for them well, and a pair of jeans that cost less than your yearly Spotify subscription can be your everyday pair for a long time.

White shirts

A crisp white shirt under a dark suit is the most tried-and-true look there is.

And you spent the big money on your suit and got it tailored just perfectly and this interview/wedding/date/etc. is a really big deal, so why would you want some cheap shirt besmirching your suit and making you wonder if you look okay and — stop. Let’s speak frankly. Breathe deeply and repeat after me: white shirts don’t last.

There is very little in menswear that has an inherently shorter life than the white shirt. It depends on how often you wear it, but a white shirt has an expiration date. Sweat, dirt, grime and all other manner of unmentionables are going to work their way in and inevitably render your beautifully made shirt ratty and sloppy looking. This goes for other dress shirts as well, but is accelerated in white, and a good laundromat can only do so much.

So you could spend a bunch of money on a luxe piece that you'll be replacing in eighteen months, or you can do the smart thing and pick out something that's affordable — so long as it still fits nicely. You should be comfortable and mobile, but not look like you’re about to board a Spanish galleon and commandeer their loot. Pay special attention to how it fits your shoulders. The seam should fall right over the point of your shoulder. Tighter will cause bunching and make you look constrained. Looser will accomplish the aforementioned pirate look.

If a white shirt is your go to — and it should be if you’re whether you’re wearing a suit frequently or not — then stock up, and be ready to replace them within two years of regular wear. And if you really want to go all-in on a really beautiful, expensive one, save it for your most luxe occasions.

Sneakers

I’m ready for sneaker-head hate mail, which I imagine is delivered in a chunky envelope with a jersey knit upper and a tiny swoosh where the stamp should be. You can line up and wrestle over pairs of Jordan’s and get into Reddit arguments all you want. I’ll be snatching up great looking sneakers on the cheap, then counting all my extra cash.

Kidding aside, if you aren’t super obsessive about sneakers and you’re just looking for something to wear on the weekends, there are plenty of good-looking options out there that will barely sting the wallet, making it a great area to save.

Like with jeans, it’s great to splurge on sneakers if the budget isn’t too tight, and having one expensive pair – like a handsome pair of nice leather low-tops – isn’t a bad idea. But there are great sneakers available for less than a hundred bucks, just like with jeans. And then when they get scuffed and the sole wears down, you won’t be crying over replacing them.

Another huge pro of cheaper sneakers is the flexibility it affords you in getting a couple of pairs. It lets you take a little bit of a risk, or do something fun with your daily look without taking a leap financially. Turns out a color or cut that you picked up doesn’t work as well as you thought with the rest of your wardrobe? Really sucks, if you spent big money. If not, it’s much easier to bounce back.

This thinking should inform any big style swerve that you intend on trying out. If you’re a little cautious about getting in on a trend, the best thing to do is get in for a low price-tag and test the waters. Even if it isn’t trendy, per say, but it is out of your lane, do yourself a favor and test it first. Nothing hurts more than putting a thousand dollars behind some capital F Fashion only to have it capital F flop and sit in the back of your closet.

Where to Spend

The Rest of Your Shoes

Unless you’re a very slim percentage of the population, you probably need more real shoes – lace-ups, leather boots, etc – than sneakers. Do yourself a favor and take the money you saved by not buying super expensive sneakers and spend it on all your other shoes

Your shoes are what stand between you and the ground, between your feet and the elements that conspire to do them harm. So, it stands to reason that the shoes you put up against the toughest, most inclement, most mean-spirited elements should be the best that money can buy. A tough pair of boots that you spend the money on now are a tough pair of boots that your grandson doesn’t have to spend the money on, because, if properly cared for, they will last forever. Trucking through rain and snow is no easy task, and it seems likely to me that Hell probably involves wearing socks that are always wet, so don’t skimp on boots.

Your shoes are also one of the first things that stands out about your outfit. Nothing will ruin your look faster than obviously cheap and/or poorly cared for shoes. You know the kind I’m talking about. They’ve never been polished, the laces are ratty, if they exist at all— they might even have that dreaded square toe that gives your foot the silhouette of a tissue box.

Think of a pair of high quality lace-ups in the same way you think about that white shirt that you’re saving money on – it’s about the cost per wear. With only a limited number of wears before it expires, your white shirt isn't a great place to spend big on. But with proper care (if you haven’t picked up on it yet, take care of your stuff), a perfect pair of shoes can be worn for decades before they look anything other than perfect.

Outerwear

The elements are here again, thwarted by your brand new, handmade, beautifully built shoes. They’re choosing a new point of attack: the rest of you. Stymie them yet again by spending more big money on your outerwear.

What are you reaching for when the rain is torrential and parking was a nightmare and you’re as far from your car as you could be? When it’s snowing like crazy and you have to trudge from the subway to work, what’s going over top of the outfit you picked out so carefully? When it’s time to break in all that sweet camping gear you bought to force yourself to put down your phone, which jacket is coming with you?

If a jacket is merely a style piece, a smart layer to guard against the lightest of autumn breezes, you can set your price point a little lower. But if it’s going to be asked to do heavy lifting, find something that will not fail. You’re asking this jacket to protect you, and possibly even an ill-prepared date, from plummeting temperatures. It would be a bad look to offer up your jacket, only to have it let the wind chill right through.

If you’re spending big money on a coat, make sure you don’t have to spend big money on six coats. Buy something versatile that will work for more than a few days at a time. I like to keep my outerwear as understated and utilitarian as possible, since it’s going to be coming off the hanger nearly every day for a few months. Statement pieces are best if that statement is seldom made.

If you’re still hesitant to fork over a whole paycheck for a coat, do yourself a favor and find something that comes with an insurance policy. There are several brands that offer lifetime warranties and free repairs on their clothes, and they happen to be brands that make great jackets. They’re often outdoors brands, whose merch is meant to be beat up a bit. They’ll do the job, and since they’re designed to be taken rock climbing, they’ll get you through tailgate season.

Something for Yourself

Lastly, let’s talk about the "treat yourself" phenomenon. This is your chance to sparkle and shine, and spend money on something for you.

Everyone has different taste, and beyond that, different things that they're captivated by. I would never spend a lot of money on a watch because they aren’t a huge part of my wardrobe, and frankly, I don’t see the appeal. But I do lose my mind over cashmere sweaters, and wear them all winter. But I know people who love watches, and I would never think less of them for spending on them. You see what I’m getting at?

Maybe it’s something that I advised you save on. If you really can’t stop thinking about a pair of super cool raw selvedge jeans, then buy them! If you’re smart and can find other areas to cut back on, and you take care of them (the ultimate lesson here), you should enjoy them.

It might not be clothes. Maybe you’re eyeing a piece of art, or a car, or a new home theatre setup. This is about you and what you geek out over. I can promise that you won’t feel guilty over spending extra on something that gets you excited, whether it’s something you wear or not.

When you find something that you really want, that is perfectly you, saving up some money for it will have an air of excitement around it. And when you hand over all those bills, you’ll know that you just made an investment into something that you'll love – and that will hopefully last you a very long time.