Perfect Fall Capsule Wardrobe

Most people, I find, don’t like cold weather. I love it. I hate being hot. It makes me feel anxious and sick. Like I can’t breathe. Does anyone else feel this way? Cold air feels clean and refreshing and calming. Like having a cool glass of water by your side when you’re in an interview.

As the days grow longer and I look forward to the coming snow, I have to remind myself to slow down and appreciate what’s happening now. Namely, weather that swings from relatively warm to pretty chilly and back again. Precipitation is still in liquid form. Everything is just a little more unpredictable in these “middle seasons” and that can make it seem like dressing for whatever is more complicated. But it doesn’t have to be. I’ve discovered the perfect capsule wardrobe for fall (and spring, incidentally). This is how I did it.

About 7 months ago (when the weather was almost identical to what it is now), we moved to a larger house. A couple months prior to the move, I packed everything I could as early as was reasonable. For a few weeks I lived out of whatever I could fit in a small weekender bag. Everything else was packed and ready to go as soon as we knew what our closing date was. I was still working from home, and it was still in the middle of the pandemic, so my choices leaned casual. But I still made some allowances for if I wanted to dress up a bit for a Zoom meeting. This forced me to pare my wardrobe down to a handful of versatile key pieces. I think you’ll find that this list covers everything from bumming around the house, to playing outside with the kids, to work meetings or dinner dates (pandemic-permitting). I also found this capsule to be perfect for any sort of light travel, as we were frequenting my in-laws’ house for sometimes days at a time.

Here is the list…

Denim Button Down Shirt or OCBD

Flannel Shirt

Olive 5 Pocket Pants

Khaki Chinos

3 Solid T-Shirts (white/black/grey)

Undies and Socks

Brown Leather Chukka Boots

Oatmeal Aran Cable Knit Sweater

Field Watch

Brown Leather Belt

Pajama Pants or Gym Shorts

Tweed Jacket

Harrington Jacket

Newsboy Cap

Not all of these things fit in my weekender bag at the same time, but that’s only because I was wearing a portion of them at any given time. If I ever had to travel anywhere during early spring or autumn, this would be my packing list. Below you will find an explanation for each item and a rationalization for why it’s included in the capsule.

Denim Button Down Shirt OR Oxford Cloth Button Down – I’ve written before about my love for my J. Crew denim shirt. It’s amazingly versatile. It can be worn alone and look perfectly unpretentious, or it can be dressed up under a sweater or sport coat. It’s also a darker wash so stains don’t show up readily, which is helpful if you are looking to stretch each item for days at a time (especially with kids around). I list the denim shirt interchangeably with the OCBD. My preference is the denim shirt, but the OCBD can do almost all the same things. Go with the OCBD if you need that extra edge of formality under a jacket for work. Brooks Brothers obviously does OCBDs but for my money it’s hard to beat the Lands End Hyde Park Oxford (although they have gone to S/M/L style sizing recently instead of specific neck and arm measurements, which makes me skeptical). My only knock on the Hyde Park is that the collar roll isn’t as robust as I would like. But when it can be had for sometimes $14, I’ll put up with some minor imperfections.

Flannel Shirt – This covers any “casual shirt” need that may arise where you need something a little heftier than the denim shirt or OCBD. Also, it can be worn as a pajama shirt on especially cold nights. I recommend the L.L. Bean Organic Flannel, specifically because of its softness.

Olive 5-Pocket Pants and Khaki Chinos – That’s right; no jeans here. What can jeans do that these two items can’t? The olive 5-pockets are just as casual but can be dressed up with a sport coat if need be. The khaki chinos are a bit smarter but can be dressed down with a sweater or denim shirt. Also, jeans wouldn’t pair as well with the denim shirt. Remember, we are going for maximum versatility here.

3 Solid T-Shirts and Undies/Socks – You don’t need as many t-shirts are you think. They are mainly for sleeping anyway as you will more than likely be wearing your denim shirt or OCBD during the day. Yes, you’ll wear it under the flannel shirt, but that’s why you have 3 of them. Choose white, black, and grey and don’t give it another thought. For the undies, I couldn’t care less. For the socks, don’t worry about it as much as I know you will. Choose some inoffensive, mid-weight socks in colors like burgundy, olive, or tan and that’s all you need. Choose as many undies and socks as you can fit in your bag.

Brown Leather Chukka Boots – Sorry guys, you only get 1 pair of shoes. You need to save space in your bag and there is no room for an extra pair of shoes. It’s hard to argue with a good pair of chukkas. They will hold up to you tromping through the mud with your kiddos, but, cleaned up, will cut the mustard at most any office or restaurant. I went with my Rancourt Acadia Chukkas, but I think a better bet would be something a bit simpler. Nisolo makes chukka boots that are sleek enough for a business casual setting, but hearty enough to carry you through all your informal adventures. They’re also pretty reasonably priced so you don’t have to feel precious about them.

Oatmeal Aran Cable Knit Sweater – This is your big gun for when the weather gets really chilly. Even though it is chunky, it is far from inelegant. Like everything else on this list, an Aran sweater can look easy and carefree when worn over a t-shirt and casual pants, or you can toggle up the formality slightly and pull it on over a collared shirt and chinos. Go with a classic, neutral color. The oatmeal or “natural” hue goes with everything and in my mind is what an Aran sweater should be.

Field Watch – I chose a field watch since it jives with the casual, “country” look that this capsule seems to strike. But really, any sort of watch will do, as long as it’s robust enough to stand up to everything you can throw at it. Don’t bother matching it to everything else you are wearing (see my earlier post on rules to keep/discard). Anything from a field watch, to a dive watch, to a dress watch will work (as long as it can handle some bumps). Yes, I understand that you can probably fit 10 watches into the crevices of your weekender bag, but the fun of this exercise is to identify the one absolute best choice. The watch I chose is my Timex Navi with an olive green strap. I have had this watch for about 3 years and it’s an absolute tank (although much cheaper than those other “Tank” watches). I’ve had to wash the strap a few times to remove the dirt, sweat, and seawater, but this thing just keeps going. I think I paid $120 for it. Money well spent. My only gripe is that the bezel is almost impossible to rotate. Oh well.

Brown Leather Belt – My personal choice on this front is a rather casual 1.5” belt with a thick silver buckle. Although a more conservative “dress” belt would work here too considering you won’t be wearing jeans. I’ve found the incongruence of the casual belt with smarter pieces like sport coats isn’t nearly as noticeable as I originally thought it would be. And the thicker belt looks more at home with the 5-pocket pants anyway. Honestly, though, any brown leather belt will do here.

Pajama Pants or Gym Shorts – You will most likely need something to sleep in. If your kids are old enough to get out of bed and randomly show up in your room in the middle of the night, you know the importance of covering your (to your children’s eyes) horrendously grotesque adult body. Let’s all try not to scar our kids for life. If the weather is skewing colder, opt for the pajama pants. Remember, if you need to, you can always pair it with the flannel shirt for bed. If it’s going to be a little warm, pack the shorts. I always think full length trousers are a better bet than shorts (when not engaging in actual exercise) so I recommend the pants.

Tweed Jacket – I recommend a tweed jacket here instead of the usual go-to navy blazer based on the tweed jacket’s ability to also act as a legit piece of outerwear. Also, I find a tweed jacket a little easier to wear in more situations. For more formal occasions you are “wearing a jacket” but in more casual situations, the rougher tweed looks more at-home than the smoother worsted wool of a traditional blazer. Tweed is also pretty rough-and-tumble so you won’t worry about it too much if the toddler is eating yogurt on your lap and spills a giant dollop on your jacket. Lastly, the tweed jacket won’t wrinkle as much when folded up and placed in your travel bag.

Harrington Jacket – It’s autumn so you’re definitely going to need some form of proper outerwear. This was a close call between the Harrington and the Barbour, but the Harrington edged out the Barbour by a nose due to its lightness and smaller size (ie easier to pack). If it’s very cold, you can always layer your Aran sweater underneath it. If it’s warm, the Harrington jacket is light and breathable enough where you won’t feel like you’re going to overheat. The only downside to the Harrington compared to the Barbour is that the Harrington cannot be worn over your sport coat the way a Barbour can. But if you need to wear your sport coat and the weather is inclement, you’ll be fine in your tweed jacket anyway (provided you’re not out in the elements for too long).

Newsboy Cap – Last but certainly not least we have the trusty newsboy cap. Easier to wear than a fedora in casual situations and you won’t look like “the hat guy”. Smarter and much more handsome than a baseball cap. Roll it up, toss it in your bag, stuff it in your pocket, pull a casserole out of the oven with it. It really does everything. My dad would be proud.

I get a kick out of whittling down my wardrobe for certain situations. It really forces me to think critically about how valuable each piece is. Consequently, I start to identify items in my wardrobe that I don’t actually need. Less stuff leads to greater satisfaction with the stuff you have. After living with just this capsule for a few weeks I developed a new love for things I had long stopped thinking about. The belt I’ve had for years, for instance. “Wow, this really is a great belt” I’d say fondly, and remember that my wife gave it to me as a gift many years ago. It also made me miss the stuff I excluded and I was excited to rediscover them when I unpacked in the new house. It was like opening a ton of Christmas presents!

We should have fun getting dressed. We all do it every day so shouldn’t it be something that gives us as much pleasure as possible? Sometimes in order to have fun with something, it needs to be simplified. That’s what I tried to do with this capsule.

Let me know what you think. Do the items I listed apply to you? Would you have gone more formal? More casual? What would you have changed?

You Might Also Like

Leave a Reply