How to Declutter Your Winter Wardrobe

It’s half past 8, it’s 25°F outside, and you’re rushing to get out the door—running late for work again. You throw open your closet to choose a coat to layer up over your suit.

“Hmmmm, which one will I wear today?

“I could go full Russian and wear the Norwegian Rain Moscow with fur collar. But that’s my favorite coat and I wore that yesterday.

“I could go full Italian with the Eidos topcoat. Ehhh, that’s too insouciant for the workplace.

“I suppose I could go full #menswear and wear the robe coat. Nah, I’ll get a hundred snide comments.

“Dang it, now it’s 20 to 9 and I still haven’t picked a coat. Forget it, I’ll wear the Moscow again.”

The signs are obvious—it’s a Tide ad.

Just kidding, you’ve got a #menswear problem.

Maybe it’s time to declutter your winter wardrobe, including—but not limited to—your sweet outerwear collection. Here are five tips to help you do so.

declutter your winter wardrobe

I wrote a little bit about this in one of my previous article. The gist is to have a system for your clothes—whether it’s shirts, trousers, jackets, coats—where it’s obvious what you have worn recently and what you have not. Doing so allows you to identify what winter wardrobe items you just don’t wear.

I don’t recommend going full Marie Kondo, assessing the specific level of joy each thing brings, then donating the rest of it—but, if there are jackets, sweaters, flannel shirts, or anything else that you haven’t worn all winter because there’s other stuff you enjoy wearing more, it’s probably safe to get rid of those things.

declutter your winter wardrobe

Allow me to state that besides the “joy” factor, there is a time that you have to acknowledge that your style has changed and maybe it’s time to get rid of old things you never wear for that reason. There was a good season or two I was still gaming the J.Crew sales to try to score good deals on V-neck merino sweaters before realizing, “wait a minute, I don’t actually wear these things.”

There’s also a time to acknowledge your #dadbod, to put it charitably. Looking at my own dad, I can see that at my age, he had roughly the same body shape as I do. But something clearly happened in the ensuing 10-15 years (at 62, he’s back to my size again, and I have a mind to kop an Eidos jacket or two for him at some point). I fully intend to maintain my current fitness level forever, but we all know best intentions don’t always go fulfilled. If you find yourself in a position of unfulfilled intent, consider it an opportunity to sell off old clothes that don’t fit and upgrade with something that does.

Besides, those old 32 waist APCs have too low a rise for your more sophisticated appreciation of higher rise denim.

declutter your winter wardrobe menswear

There’s a point where you can declutter too much. I know because I’ve been there. My friend Jonathan had gotten engaged, and for his bachelor party, we went paintballing—in March (in Ohio). Sounds like a great (if freezing) time, except I had purged my closet of nearly everything I might’ve been okay getting covered in paint. I wore pebble-grain chukka boots from Banana Republic that up until then were still in somewhat regular rotation (this was early in my menswear transformation, cut me some slack). So while I enjoyed the final gauntlet we put Jonathan through (he had welts all over his body for his honeymoon), I was definitely not appropriately dressed for that day.

These days, I make sure to have stuff in my closet or in storage bins downstairs so that I’m not caught without the right gear. Like a few weeks ago when I dug a trench outside my house for drainage in 30° weather after a week of heavy rain. I was glad to have a fleece, old jeans and some old boots to work in the mud in.

declutter your winter wardrobe men

Back in my merino V-neck wearing days, I recall having a perfect navy sweater. It was from Banana Republic and I wore it to great effect all the time (in particular over a blue gingham button-up shirt—you know the one). But even then I recognized that Banana quality left something to be desired, and there came a point within 2-3 years that it was clearly showing its age. I knew I needed to replace it and reduce how often I wore it.

I’m not the kind of guy to, say, buy seven identical pairs of shoes so as to spread out the wear and tear amongst them and prolong their natural life. But I do think it’s good to recognize those things you’ve identified as your best-of, favorite items (see point 1), and when there’s an awesome deal on the same or very similar thing, you can buy it to keep the magic alive. Depending on what it is, you can take advantage of seasonal sales, especially if you’re under no time pressure to immediately replace it.

declutter your winter wardrobe outerwear

The coat matrix skews admittedly toward a tailored-favoring audience, so I apologize to the streetwear guys. But it can be useful for classifying the coats in your wardrobe, which will, in turn, help you spot gaps (or surpluses in certain categories). The gist is to break your outerwear into categories based on the level of formality level, and how warm they are.

It’s fair to say that the colder months are more ripe for dressing well because of all the layering opportunities and wealth of great clothing categories (sweaters, outerwear, scarves, etc.). The flip side of that is that the risk of over-stocking your closet to the detriment of warm-weather attire. You need to save some room in your wardrobe so you can look great all year round—not just when it’s freezing outside.

Use these five tips to help free up some space and clear out the cruft of your wardrobe. Of course what you do with that newly vacant space is up to you. Something tells me it’ll quickly be filled again.

Building a Capsule Wardrobe, Pt. 2

In part 1, we took on the first steps in building a capsule wardrobe: we figured out where we are on our sartorial journey and made an aspirational list of what our ideal wardrobe would be. Next comes advice on figuring out not just what would be ideal, but what’s practical.

Figure out what looks good on you

This can be tricky because it’s hard to be objective about yourself. You get excited about the fabrics and the craftsmanship and the steez! But on the flip side, who can you trust to give you solid feedback? I’ve found that a lot of advice from third parties falls into one of two categories: 1) Inexperienced advice from a non-menswear-enthusiast perspective that’s ill-formed and doesn’t take into account any of the Important Knowledge about the clothing that you have, or 2) Advice from enablers, those fellow menswear enthusiasts who can’t be objective either because they do know all the Important Knowledge, or are blinded by the cachet of your item (“dude that thing is sweet, you have to keep it!”).

It helps to have photos taken of you wearing stuff to see how it looks. Post the photos in the “What are you wearing today?” threads, and listen to the feedback you get from guys whose style you respect. If you disagree or don’t understand where they’re coming from, ask questions. Be teachable. If you’ve been thoughtful about what need you’re looking to fill in your wardrobe, you can share that and ask if they think it fills that need. You need to be honest with yourself based on all the evidence and advice – do you actually look good, or not so much? 

My litmus test for what I think looks good on me is essentially this: if I can relax while I’m wearing something without constantly adjusting it, then I’ve got a keeper. I’ll feel comfortable in my natural style because I think it makes me look good and fits well. If you’re fidgeting or adjusting it, that means it probably doesn’t fit well, or you’re not comfortable wearing it. It could be that you’re wearing something you like the idea of, but which looks wrong on you, in which case go back to step 2 (making a list). If you’re wearing something you aren’t comfortable enough to just live in, you may be wearing somebody else’s life uniform.

Temper your aspirations with reality

Here’s the thing: your ideal aspirational wardrobe can’t carry you on its own. It has to clothe you in your day-to-day life. My perfect wardrobe would include a midnight navy with black-facing shawl lapel tuxedo, a white dinner shawl lapel dinner jacket, suits in navy, charcoal, mid-gray, and POW flannel, 8-10 seasonal sport coats, a dozen or more seasonal ties, a half dozen pairs of Edward Green or John Lobb shoes, etc. I would look better than the Prince of Wales himself! But with that wardrobe, what would I wear when we’re grilling outside with friends over at our house? And when will I wear that white dinner jacket?

The clothes that I really love—tailoring, in my case—don’t make sense for many of the types of activities I actually spend time doing. And let’s be honest, nobody really should be wearing tailoring to a barbecue. So you’ve got to put some thought and effort into versatility in your wardrobe. In my case, jackets that are easy to dress up and down, sweaters that can layer under a jacket but also look good on their own, nice casual shirts and pants, and so forth.

Clothes are meant to be worn. Having and maintaining a capsule wardrobe requires that you don’t “save” your nice clothes for “special occasions.”

On top of that, there’s always the specter of opportunity cost. You must prioritize which categories of clothing are most valuable to you and what you wear the most, so you can spend accordingly. For me this means I have to “settle” for a Kent Wang instead of a Luca Avitabile polo to layer under one of my Eidos sport coats. As long as you are wearing something you like and look good in, you’ll convey a personal style that eludes the vast majority of people.

Use this as a guide to organize your thoughts in developing a capsule wardrobe. Be aware, however, that no matter how carefully you try to plan, you will discover that your tastes will change, your life circumstances will change, and what you thought was a “complete wardrobe” in the past has become lacking in some critical way. That’s okay. Continue evaluating, always being honest with yourself and never stop paring down.

How to Build a Capsule Wardrobe, Pt. 1

We’ve all wondered how to build a capsule wardrobe: that ideal state where your overtly materialistic tendencies are replaced by Zen-like peace of mind; you dress how you want every day, you own only what you wear, and you are one with the Force. Nobody lives this way, but it’s a nice goal. In this two-part article, I’ll elaborate a bit on the thought processes you can take to work towards it. In part 1, we’ll focus on who you are, and what you’d like to wear.

Appraise your current wardrobe and where you are in your menswear journey.

Are you a newbie who’s just getting into clothing? That is, you’ve just come across Styleforum and are realizing that everything you know is wrong? Or have you already amassed a large wardrobe of clothing, but still find it difficult to decide what to wear?

In either case, you have much to learn, and I’m not just talking about the “rules.” I mean about yourself—your style; the version of yourself you want to project through your clothing that is most sensible for your lifestyle and life’s circumstances. If you’re just starting out, resist the urge to buy any and every awesome piece of clothing you see on B&S/eBay/deep discount. You will do yourself a great favor by just making do with your current wardrobe while you figure things out. How do you “figure things out?” You observe and participate in discussions here, and find the “Coherent Combinations for Beginners” cached Internet Archive thread from Voxsartoria.

If you’ve got an already-large wardrobe, pay attention to what you come back to time and again. Pare your closet down to what you actually wear. I alway put my most recently worn shirt to the furthest right in my closet. I almost never get more than 8-10 shirts deep before I’ve washed them and start over again with those same shirts. All the shirts to the left of that are either: 1- Seasonal shirts (madras or linen or Oxford), or 2- Shirts I don’t wear. You can probably safely get rid of the non-seasonal shirts you don’t wear except for the ones you need for special occasions. Figure out a similar system for trousers, jackets, and even shoes.

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A capsule wardrobe will free up closet space, which just feels good. And unless you have unlimited funds—and assuming what you own is quasi-valuable—you can get actual money out of these obsolete possessions. Sell them on the buying and selling forum, and use that money to upgrade what you keep.

Make a list of what you would want to make your dream capsule wardrobe. 

Making a capsule wardrobe is like packing for vacation: you need versatility, where everything goes with almost everything else. But this is more aspirational—you are picturing what you really want in order to become the best-dressed version of who you want to be. In my case, I actually created a Pinterest board with photos of cool clothes (I found out later a bunch of those pics were of @NickPollica – the Creatie Director at Eidos – before I knew who he was; go figure). I wanted to have a “complete wardrobe,” and I had a bookmarks folder with links to actual products that matched those inspirational photos.

how to build a capsule wardrobe building a capsule wardrobe styleforum capsule wardrobe

This step is the most important, because you’ll find all kinds of awesome stuff on sale that you’ll love and which would totally make your life better if you owned it. But your goal isn’t to buy everything that’s awesome, it’s to make a lean, wearable, flexible wardrobe. Having this list will help you when you’re three sheets to the wind and that Mt Fuji kimono is on clearance at No Man Walks Alone. You can pull it up and remind yourself of what you actually need, not just what would make you the coolest dude this weekend at Acme on Broadway in Nashville.

Having this list also helps you to upgrade what you already have systematically, piece by piece. For instance you may have a workhorse Brooks Brothers suit, but now prefer Italian tailoring. Once you know what in your wardrobe needs to be upgraded, you can start looking for the best replacements.

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