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A Step-By-Step Guide to Starting to Dress Well for the Risk-Averse Neophyte

Extract from https://www.reddit.com/r/malefashionadvice/comments/1laa42/a_stepbystep_guide_to_starting_to_dress_well_for/

A Step-By-Step Guide to Starting to Dress Well for the Risk-Averse Neophyte

It’s a common refrain here on MFA. “How do I get started?” The linked articles in the sidebar are going over your head; the inspiration guides and discussions at the top of the page are no help; you’re scared of shelling out hundreds of dollars in new clothing only to find out that the items were poor-quality, or ill-fitting, or just plain bad.

You want to start dressing better but don’t know where to start.

Hopefully, this article can help. What we’re going to do is narrow the process down to precise, discrete steps, in order to a) avoid information overload, b) prevent wasting money through ‘shotgun shopping’ (buying a whole bunch of items at once because someone told you they were “necessary basics” or “wardrobe staples”), and c) give you a path to move on from where you are and expand your sartorial horizons. We’re not going to really change your style but, perhaps, refine it, simplify it, and make it a basis for further expression.

WHO is this for: The rank neophyte, someone brand new to the idea of putting effort into dressing well, or at least doing so in an informed way. Particularly, someone who has an aversion to risking buying things that don’t fit, are out of style, or don’t work with their lifestyle - in general wasting money. If you like going out and jumping into the deep end and trying things out, or have money to burn, this may not be for you.

HOW will we do this: By a step-by-step guide that cuts down on the amount of information you have to parse, allowing you to focus on one clothing item at a time. Also, by getting you to think about how and what you wear and why, and having that inform your decisions, rather than wardrobe lists or MFA uniform standards.

This isn’t the only way to start thinking about dressing better, or even the best, but hopefully it can help you avoid some common pitfalls.


Steps

1) Lurk And Read (and keep doing it!)

2) Make An Honest Assessment Of Your Current Style

3) Pick One Item You Already Wear (a lot)

4) Research The Heck Out Of It (and figure out what works for you)

5) Go Shopping (Try Before You Buy), And Purchase

6) Integrate Into Your Wardrobe

7) Lather, Rinse, Repeat

8) Try New Items And Styles One At A Time


1) Lurk And Read (and keep doing it!)

You’re already doing it, to an extent. Keep it up! Read through articles and discussions, even if you don’t know what’s being said. Use RES to save comments and threads you find interesting. Make a folder in imgur and tuck images from inspiration albums or other threads there that you find interesting to save for later. Ask polite, pointed questions if you don’t understand something.

Work through the sidebar and wiki. There’s a ton of information there to be digested. Read articles fully, don’t skim. If you don’t understand something, Google it, then ask in the Simple Questions thread. Browse through the WAYWT and see what you like and what you don’t. Maybe ask the users about a particular item if you like it.

Go outside MFA. Lurk tumblr, StyleForum, Superfuture, Ask Andy, and others. Check out some of the blogs listed in the sidebar.

Above all, keep an open mind. Never say, “I don’t like this, it sucks”. Ask, “I’m not a big fan of this, can you explain the appeal to me?” Soon you may find yourself drawn to and enjoying styles and items you would have scoffed at mere weeks ago.

Keep this up, and you’ll be able to consider where to go once you’ve gotten some of the basics out of the way.

2) Make An Honest Assessment Of Your Current Style

What is your everyday outfit, right now? Sneakers, jeans, and a t-shirt? Slip-on leather shoes, dress slacks, button-up, and tie? Workboots, canvas pants, and a torn hoodie? Dark suit, black shoes, power tie?

Make an honest and concise analysis of your most commonly worn items. For the sake of this article, I’m going to work with the example of a typical jeans-and-t-shirt guy.

A NOTE ABOUT FORMALITY: Dressing up doesn’t mean dressing better, and dressing well doesn’t mean dressing up. Many guys fall into the trap of feeling like they need to put on a suit and tie to dress and look good. This couldn’t be further from the truth. Be honest about who you are and what’s appropriate for your life. If you’re in high school or college, wearing a suit would be completely out of place. If you’re in a casual workplace, wearing a suit or jacket when your boss wears jeans would be inappropriate and might look self-serving. There’s nothing wrong with a t-shirt-and-jeans outfit, or chinos and OCBD, or streetwear, or yes a suit. But all of these can be executed well, and all can be done poorly.

3) Pick One Item You Already Wear (a lot)

Looking back at your analysis of your everyday clothing, what is your most commonly worn item? What stands to gain from the most improvement? Where would you feel most comfortable making a purchase?

Start with something that will have some impact, some benefit in your overall look. Don’t think about periphery items or accessories like ties, watches, or sunglasses. Focus on a basic, foundational item. Jeans. Sneakers. Dress shoes. A t-shirt. A suit. A button-up shirt. Boots.

The reason we’re starting with something you already own and wear, is that it should be easy to integrate into your life and current wardrobe. After all, you’ve been wearing what you’re wearing for a while now, and I’m going to guess it hasn’t caused you too much trouble.

For the purposes of this guide, I’m going to stick with the example of jeans.

4) Research The Heck Out Of It (and figure out what works for you)

Take some pictures of yourself wearing the item you’d like to research that you currently own. Wear neutral items aside from it (like a white tee and plain sneakers). Use natural light and get a friend to take them or use a timer if possible. Here’s some other tips for making a good photo. Blur or cut out your face, and post to the Outfit Feedback and Fit Check thread or Simple Questions. Ask specifically for people to analyze the particular item you’re looking into, what can be improved, and any recommendations they have.

Taking those notes in hand, read up on whatever you can. For jeans, feel free to check the sidebar article, r/rawdenim, search “denim” or “jeans” in the search bar, find out everything you can. Figure out some options to look into that are available locally and…

5) Go Shopping (Try Before You Buy), And Purchase

Head to the store and look to try on some jeans. Take whatever recommendations you’ve been given, grab a pile of jeans, and try them on. Feel free to try pairs that aren’t what you consider your normal size or cut. Try them on in the dressing room and take some pics of yourself in them (again, simple items aside from the jeans make this easier to assess). DON’T feel the need to buy anything just yet.

Take those pictures back and post them, again, to the OF&FC or SQ threads. Get opinions and think about which ones you like best, outside of the store.

When you’ve decided which ones you like best (you may have to try multiple stores or take multiple trips), go ahead and make the purchase. It may be worth waiting for a sale, but in my opinion it’s better to just get what you want and looks good, even if it’s full price, rather than settle for something else.

6) Integrate Into Your Wardrobe

Take the new item and work it into your rotation. Wear it regularly and see how it fits in real life. Is it comfortable? Does it look good? Does it work with the rest of your clothes? Even if it doesn’t, can you think of what you might change with your other clothes to suit the item better? For example, if you go from fairly baggy jeans to a slimmer cut, you may find your shirts are too large to look good with it, or your sneakers look a little chunky. That’s something to consider before making your next purchase.

7) Lather, Rinse, Repeat

After assessing the new item and how it fits into your style, you can begin to think about the next item to deal with. Maybe it’s some boots to go with those jeans, or an OCBD to wear over it. Either way, think about how it would work with your style and start your research again.

8) Try New Items And Styles One At A Time

After a few rounds of this, you’ll find you have a tidy little wardrobe of decent clothes that works well for you, but you may find things to be a little bit boring. With a stable of basics you can depend on, now you can branch out and try some new things without too much risk. Maybe pick up some cheap stuff from H&M or elsewhere to try a new style, or snap up a more expensive item you’ve been thinking about and pining after. Look through the WAYWT for some ideas, save the images you like in a folder.

Maybe read this link about developing personal style for when you’re looking to go further. Keep reading, looking for inspiration, and going to places other than MFA for more and more info. Move forward and take some risks, knowing you have a basis to fall back on. Most of all, have fun!