The Two-Season Wardrobe: My Menswear Essentials

two season wardrobe menswear essentials

One of the requests I occasionally get here is to write a piece on my “essentials.” These sorts of articles are always fun to read, but I didn’t really feel that I had anything new to add to the mix. Navy or gray suit, raw denim, OCBD, etc – what more is there to write about? Well, now that my wardrobe is pretty filled out and I have most of the things I need, I’ve started to notice an interesting pattern in my purchases. Without really planning it, I’ve built the same “essential wardrobe” twice – once for warm weather, once for cool weather. I wasn’t really an intentional method of building out my closet, but I’ve since put some thought into it and think it’s actually a fun way to approach things. So without further ado, here’s my go-to clothing – the Two-Season Wardrobe.

The main concept here is that most of my core items come in two variants for the two major seasons. This has given me a healthy amount of variety while still being able to settle into a comfortable pattern of dress. It’s also allowed me to keep my “look” fairly consistent between seasons (although admittedly some of this is due to San Francisco’s mild climate). I should note that not all of these items were ones that I expected to use a lot; in a sense, this wardrobe was sort of self-selecting. When things worked well, I made sure I had enough of that thing to get me through the whole year. This is the result of that.

I should also mention that what I highlight here is a result of how put together I need (or choose) to be on most days – others will undoubtedly be more or less formal that what’s shown. Like many men, I’ve found that my day-to-day style requirements are fairly middle-of-the-road in terms of formality. In other words, it helps to be a little put together but formal dress is certainly not required (and would likely be too much).

With that, here’s what I’m almost always wearing, starting from the bottom:

Calfskin Longwings

For me, longwings have become the most versatile shoe in my wardrobe. I wear them with denim, chinos, odd trousers, and, on the rare occasion, suits. They’re also my favorite welted shoe to travel with, since they cover so much of the formality spectrum. You could easily substitute another brown blucher (like a plaintoe blucher for instance), but I enjoy longwings for their added visual interest.

Shown: Alden 979 and Allen Edmonds MacNeil

Other favorites: Carmina, Meermin, Grant Stone

Suede Chukkas

I wear suede chukkas more often than any other shoe. I have three pairs currently, and might pick up another. They’re my go-to with jeans and often with chinos, and even sometimes with odd trousers. They look great in calfskin or cordovan too, but I just like the knockaround look (and low maintenance) of suede. It’s unlikely that anyone will get super excited about chukkas (well, I guess there was that one time) but it’s a shoe that you can rely on all year round. What they lack in sex appeal they more than make up for in wearability.

Shown: J. Crew “Bennet”, Allen Edmonds x Massdrop unlined chukka (a product I designed, so close to my heart)

Other favorites: Alden, Meermin, Carmina


It’s not really news that denim is a cornerstone of a modern wardrobe. I never got deep into raw denim like many others did (I’m just not a huge fan of wearing uncomfortable clothing), but I do respect the people that are able to turn denim into art projects. For me, I tend to stick with two pairs – a new, raw (or just dark) pair that I usually start breaking in during the fall, and then a well-worn pair that gets used mostly in the summer (all the holes are just extra ventilation, I guess). The colors sync up well with the rest of my seasonal clothing, too – deeper, saturated colors in the winter and lighter, more dusty tones in the summer.

Shown: A.P.C. and 3Sixteen SL-100

Other favorites: too many to list.


Back when I was working on the In-Between Wardrobe miniseries, I wanted to write an entry on pants. The problem was that it was going to be a really short article – just wear chinos. Chinos are the ultimate middle ground option, case closed. I wear chinos almost every day. If denim is casual and trousers are formal, chinos are right there in the middle. I’ve experimented a bit with different fabrics but always come back to classic cotton. I’ve tried a variety of colors as well, from three different shades of white to Nantucket Red, and have found that I like earth tones (olive, caramel, brown) in the cool months and pale colors (cream, white, light gray) in the warmer seasons.

Shown: J. Crew 770 chinos in off white and caramel

Other favorites: see here.

Brown Belts

 Nothing too wild here, just some belts to keep my pants up. These are 1.5″ across, which I find to be the most versatile width in terms of formality. Although I don’t subscribe too deeply into the “match the belt to the shoes” mantra, I do generally wear the lighter belt in the summer since my footwear tends to go from dark brown to mid-brown and tan (as seen above). Buying nice belts is worth it since you can wear them thousands of times in your life – it’s an easy box to check and then never have to think about again (just one more reason to keep your waistline in check).

Shown: Equus Leather in Australian Nut and Oak Brown bridle

Other favorites: The British Belt Co, Guarded Goods, Allen Edmonds

Blue Dress Shirts (with a textured fabric)

Ah yes, the classic OCBD. Dress it up, dress it down, etc etc. While I tend to stick with oxford cloth for my “in-between” shirts in the fall/winter, my spring/summer shirts are often made of chambray. It’s usually a bit lighter and feels more appropriate for warm weather. Besides that, they’re pretty similar – cut long enough to be tucked, a hearty soft collar, and always in some shade of blue.

Shown: Proper Cloth in chambray and heavy oxford.

Other favorites: Kamakura, Brooks Brothers

Plaid Shirts

 Here’s where things get a bit more casual in the shirt department. While I certainly have dressed these shirts up, I usually wear them untucked over denim or chinos. For spring I “spring” (heh) for madras, and when the weather cools I switch to flannel. Both are usually adorned with fairly bold patterns to make them more casual (and to help me camouflage in a tech-y city).

Shown: Proper Cloth madras and flannel from a couple years ago.

Other favorites: Kamakura, Brooks Brothers

“Greige” Sweater

My high internal temperature keeps me from wearing sweaters too often, so I relish any day that I get to slide into one. For me, crewneck is the only way to go. While I get how a V can look good in theory, I just love the preppy appearance of a button-down collar popping up through a crew. Also, a crewneck is a bit more casual so looks good in a broader spread of formality. Plus, I think Vs had a bad run in the last 10 years, where they were generally portrayed as thin, shiny merino under a too-skinny suit. I much prefer sweaters with heft and texture. For spring, I’m more likely to reach for a sweatshirt since it’s significantly lighter. It’s also more casual (I wouldn’t wear it under a sportcoat, unlike the shetland wool one), and I think that it works well under light jackets and with jeans. Either way, things in the tan/gray spectrum are what I always end up getting – since I often wear sweaters against navy, brown, or olive, I want a color that will look good with any of those (and isn’t too dark, since most of my pants and outerwear is in a more saturated tone).

Shown: O’Connell’s Shetland and Velva Sheen Sweatshirt

Other favorites: Inis Meain, RRL, J. Crew, Club Monaco, John Laing

The Navy Blazer

If you’re reading this article then you probably don’t need me to explain why a navy blazer is a great thing to have, so I won’t bore you with that. These sportcoats are identical in many ways – a slightly lighter hue of navy, three roll two closure, hip patch pockets, half lined. There are only two differences – fabric and buttons. My warm-weather blazer is hopsack, for higher breathability and a touch of sheen. I paired it with mother-of-pearl buttons to give it a sporty, almost nautical vibe (especially when paired with white pants). The other is a mid-weight flannel, a classic fabric for cool weather (natural horn buttons seemed like a perfect pairing). Either way, these are what I usually reach for when I want to look a bit dressed up but no so much as to draw attention to myself.

Shown: Beckett & Robb blazers in hopsack and flannel

Other favorites: Suitsupply, Eidos, Ring Jacket

Field Jacket

I absolutely love field jackets. There are plenty of other types of jacket that are equally approachable, but for my tastes the slouchy, pockety-y style of a field jacket is what I always gravitate towards any day I’m not wearing a blazer (which, these days, is most of the time). I’m using the term ‘field jacket’ loosely here – to me, it’s a piece of outerwear with a shit-ton of pockets and usually some sort of belt or drawstring and a standing collar. M-65s are the classic example, but there are many styles out there. My warm weather coat is a lightweight cotton layer, and my cool weather one is made up in hearty waxed cotton.

Shown: GANT Bouquet Garni (Spring 2011), Private White VC Twin Track

Other favorites: J. Crew, GAP, and others

The Rest

It’s worth noting that there are some pieces that I have omitted here that I would still consider essential, but they tend to be “four season” pieces and don’t change so much with the weather (they also tend to be a bit more formal or more casual than I regularly dress). Examples of this would be a navy suit, black captoes, gray pocket tees, and white sneakers. Those are go-tos regardless of the season if the level of formality (or lack thereof) calls for it.

Beyond that, that’s pretty much it. As the seasons start to change, I tend to blend these two sides together a bit, and between all this i almost always have something appropriate to wear. It’s nothing new or wild, but it works for me. What are your essentials? How does seasonality affect what you wear?