You just won the lottery. You got your tax return back. Your parents gave you some money and a couple of gift cards as a graduation present. You’ve finally reached your target weight, and none of your old clothes fit anymore. Now, it’s time to reward yourself with a new wardrobe. You’ve got $X. How do you spend it?
Stop.
Breathe.
This is what you should do.
First: Four simple rules.
1. Read the sidebar, and then the wiki. - No, really, go read it. If you’ve already come this far, you’re clearly making some kind of effort to look better. Take some more time to look through it. Read it right now. Not all at once, not all with equal attention, and don’t expect to absorb everything your first time through. Read it multiple times, and take it in one bit at a time.
Start with the “Getting Started Section”, and then the seasonal guides. Those are the most important. The rest you can read at your leisure.
2. Figure out your personal situation. - Who are you and what are you dressing for? Are you looking to update your work wardrobe? Are you a student in college looking for a more “mature” look? Do you live in Canada or are you moving to Texas? Dressing well doesn’t exist in a vacuum, and your context determines your wardrobe needs. Ask yourself the questions asked in this comment made by /u/Schaiparelli .
In a similar vein, figure this out: What do you have? What you need? Prioritize the things you’ll need, like a winter jacket or a suit (or two). If you’ve already got 4 dress shirts, you don’t need to buy more immediately, even if they don’t fit well.
3. Buy well-fitting, versatile basics. - What does this mean? Hopefully, you’ve read rule #1 and you’ve seen the guide to the Basic Wardrobe. That means you’ve seen the three key principles : Fit, Versatility, and Simplicity. These are the most important things to consider when you’re starting fresh.
FIT: There’s a reason the “How Clothes Should Fit” guide is the first guide in the sidebar. Fit is the most important factor to consider when buying clothes. Case in point: Daniel Craig in 2002 vs Daniel Craig in 2012. Cheap clothes that fit well are always going to look better than expensive clothes that don’t.
VERSATILITY: Buy neutral-colored clothes that can be easily mixed and matched with each other. Don’t try to buy 3 “outfits”. Instead, if you buy versatile items, say, 3 shirts and 3 pairs of pants, and you’ll have 9 outfits that look good. Check out the Color Guide and "Building Outfits that Work" for more on this.
SIMPLICITY: This usually goes hand-in-hand with versatility. If you put a bunch of versatile items together, you’ll end up with a clean and simple look. There’s no shame in simplicity, especially as a beginner.
These three concepts: fit, versatility, and simplicity, work together to create the idea of “basics”. For a beginner, this is the easiest and best way to start a new wardrobe. Once you’ve filled in the gaps of things you need with well-fitting, versatile basics, you’ve created a strong foundation for your wardrobe. From there, you can build on it in any way you’d like.
4. Don’t spend all of your money at once. Seriously. Take all of the money you’re ready to spend and put it in the bank. Blowing all of your money on clothes at once is a bad idea, and 6 months from now, you’ll regret it.
It’s too easy to go overboard on buying “basics”. For a beginner, unless we’re talking socks or underwear, you don’t need more than 5 of each item, and more than 3 of any type of item is excessive. You’ll end up wasting money on things you don’t need, and then you’ll miss a great deal on something you love.
Don't buy something just because it's cheap. Sales are your friend, but don't ever justify a purchase with "it's only $20". If you can't think of 3 outfits you can wear it with, don't buy it. That's $20 wasted.
Even if you’ve read the sidebar guides 10 times each, I can guarantee that you don’t fully understand the key principles of fit, versatility and simplicity yet. Discerning whether something fits well or not is a difficult skill to pick up, and it is even harder to apply to yourself. It can only develop with experience.
Your tastes will change a lot in 6 months. Take a note from the guide to “Developing Personal Style”, and start collecting a folder of outfits that you like. You’d be surprised at how much your taste will change.
Trust me: buying everything at once will lead to a pile of mediocre clothes, disappointment, and thoughts of “why the fuck did I buy that?”. Instead, start with buying slowly and buying cheaply. Think hard about your purchases before making them.
Our Plan of Attack:
Step one: Figure out your context.
Remember rule #2? Make a list of things you have and a list of things you need. To make these lists, rely on the appropriate sidebar guide, usually the Basic Wardrobe Guide.
Step two: Try on as many new things as you can, without buying anything.
If it’s on your list, go to the mall to see if it works on you. If it's not, try it on anyways. Bring someone with you and see if they like it, or take a pic and post it to the Official Feedback and Fit Check thread. Remember: there is no definitive list of men’s wardrobe essentials; there are only suggestions. What you need to do is decide if and how an item works for you. If it doesn’t, take it off your list.
Step three: Prioritize the purchases you will make.
What do you need immediately? What do you already have enough of? Your absolute priorities (ie. suits or dress code items) should be your first purchases, followed by the things you need. If you have trouble deciding, consider what you have already and which item is more versatile.
Think of buying an item as paying to unlock more outfits. Would you rather pay $30 for a shirt to create 2 new outfits, or $60 for a jacket that will create 10 new outfits? A good general rule is to prioritize items in this order: shoes, outerwear, tops/bottoms, and accessories.
Step four: Start shopping with purpose.
Don’t shop without knowing exactly what you are looking for. Shop around, but don’t yield to the temptation of the sale section. Try things on and compare the price, fit, and quality. Keep looking until you’ve found something that’s right for you.
Step five: Don’t buy it just yet.
Put your potential purchase out of your mind for a week. Then come back and look at it with fresh eyes. Is it still a good idea? If the answer is yes, go ahead and buy it.
Step six: Repeat.
Repeat until you’ve built a collection of well-fitting and versatile basics for your wardrobe. By now, you should have a good eye for fit, and you have the taste to make purchases on your own without needing to wait and think about it.
Now what? For some, this is the end point of their fashion development. But maybe, by now, you want to expand beyond the basic wardrobe.
Step Seven: Develop your personal style.
From here, you must discover your own path. Listen to the tips in the “Developing a Personal Style” guide, and work from there. Hopefully you’ve been keeping your personal inspiration album. That’ll give you a direction to start off in. What happens next is up to you.
So... I’ve Got $X. What should I buy?
THE LONG-AWAITED ANSWER: What you should buy depends on your personal situation, your needs, and what you have already. Seriously, did you not read any of the words above this?
No, but seriously?
If you want a list of things to buy, check out the basic wardrobe guide, and the assorted lists of essentials that “all men should have in their wardrobe”. Also check out these wardrobes that others have made for themselves. Don’t take their (or our) word for granted. Try things on, make sure they fit, and see if they work for you. Remember, don’t spend it all at once.
But I don’t like the Basic Wardrobe:
Check out what the FAQ has to say.
When shouldn't I buy something?
Check out this post on styleforum and the comments that follow for a list of reasons you shouldn't buy something. Check out the rest of the thread, if you have time, too!
So I kind of lied. I wasn't trying to literally answer the question, "How should I spend $X?". Instead, I addressed the underlying question: "How can I start to look better?" The answer, of course, is to read the sidebar and lurk on MFA. However, it's harder than it seems, so I wrote out a guide to getting started on a new wardrobe.
Building a wardrobe that works for you is a monumental personal task, and unfortunately, there’s no quick and simple shortcut. No one can "give" personal style. If you simply purchase the list of clothes that someone (a stranger!) gave you over the internet, it generally won't work for you because of problems with fit, personal style, and/or creating outfits.
If you need personal advice on getting started, feel free to make your own post and ask your own questions. But before you do, try to answer some of the questions I posed here. Generic questions will only receive generic advice. The more specific you are, the more useful the advice will be.