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The Top 3 Essential Wardrobe Items for Each Season of the Year
20 · 08 · 2020

The Top 3 Essential Wardrobe Items for Each Season of the Year

Written by Tigre Haller

Just like Vivaldi’s eternal composition, The Four Seasons, winter, spring, summer and fall strike different tones, arrive with their own particular challenges, are a lot of fun, and require special attention.

Here we will talk about the 3 essential wardrobe items (and then some) every man should have for each time of year. Even if you live in a climate that’s always cool or always warm, we’ve got you covered.


mens summer essentials


Men’s wardrobe essentials for summer is a pretty open field. 

Tucked in or free-flowing, solid colors or patterned, a long or short sleeve collared shirt is always a safe choice to pair with shorts. And, they look killer when layered over a t-shirt.

But, nothing says “summer” more than a t-shirt, nice pair of shorts and sneakers, right?

That’s why these items are summer essentials.

Even though this look can be the ultimate in summer cool, you really need to know how to select each item.

1. T-shirts

V-neck or crew tee? Believe it or not, this is a hot debate.

Which one you choose is a matter of personal taste and personal shape.

Crews work best if you have a slender build and frame as the shape of the crew neck creates the appearance of squarer shoulders. The crew is also ideal if you have a longer neck and / or a narrow face since it will help to balance those features.

V-necks on the other hand, literally open up some space to add some length to shorter necks and fuller faces. Be careful not to get a v-neck that plunges too deeply. Showing off some well-groomed chest hair and your sculptured shape can be attractive, but too much is too much.

The material your tee is made of is incredibly important. Opt for 100% cotton as it is a natural fiber that breathes, is comfortable, sturdy and doesn’t cling.

Whichever collar and material you choose, t-shirts should not be too baggy or too tight. If you are on the weighty side, opt for something with some room. if you’re fit, you can go a little slimmer, but not so much so that it becomes a muscle shirt. The key is to flatter your physique.

2. Shorts

Shorts should never be too loose or too tight. Try to avoid the cut-off or ripped jean look. As discussed in my blog A Man’s Guide to Wearing White Sneakers, shorts should sit above at about 2 to 4 inches above the knee. Look for twill or French terry for shorts that are relaxed and comfortable, and always look good.

3. Sneakers

Finish your summer look off right with a sleek pair of white sneakers, like our minimalistic Reids. Or, for a dressier but still casual vibe, go for the classic Penny Loafer like our Cohens.

Youll always need something to slip on when the sun goes on. That means a nice hoody, maybe a jean jacket or a sporty blazer.

And, oh - please dont forget the sun block, and follow these cool tips to Beat the Heat.


fall wardrobe essentials

Men’s wardrobe essentials for fall call for layering.

Fall is fantastic. Crispy cool days, chilly nights. Leaves start to change color, Halloween and Thanksgiving are on the horizon and you get to start layering up.

1. Shirts

That means a classic Oxford shirt or nice turtleneck. Look for fabrics that have a little heft, but not so much that you will feel smothered. You might also want to wear an undershirt as your first layer of defense.

2. Sweaters

Then, add a sweater like a v-neck or a cardigan. A rugby shirt is a great option for fall as it incorporates the best of shirts and sweaters.

3. Trousers

Choose wool, denim, corduroy or a heavier cotton twill for your trousers. Each of these fabrics have enough weight to keep the chill away, but they are still highly breathable.

Top off your look with a jacket made of tweed, leather, suede or corduroy and an autumnal scarf, and you’ll be ready to roll around in the leaves or to make a scarecrow. Don’t forget the hot apple cider. Yum.

Boots, like our sleek Bolton Chelseas, are another fall essential. The sleek profile looks amazing with all of the items mentioned above, and they are so easy to slip on and off. Trusty Dunham Derbies will also look very attractive with any of your fall outfits.


winter wardrobe essentials

Men’s wardrobe essentials for winter can get really heavy.

A lot of your winter wardrobe depends on how cold and wet it gets where you are.

1. Hats

Did you know that most of your body heat actually escapes through the top of your head? A hat, like a beanie, cap or a fedora is essential to keep the warmth in and avoid having to wrap your scarf around your head.

2. Scarves

Speaking of scarves, no winter ensemble would be complete without one. Long, short, in between, patterned, solid, it’s all good. Just make sure your scarf is made with a breathable material that won’t irritate your skin. When it’s extra cold, go ahead and wrap it around to protect your ears.

3. Jackets

A heavy jacket, like a parka with a hood or one stuffed with down, is a no-brainer. A shearling coat is another great choice, as is the classic camel top coat or a wool overcoat.

Trousers should be made of heavier, substantial material that will keep the chill out and the warmth in. 

Keep your feet warm and toasty with a substantial pair of Boots. They wrap you up like a warm blanket, provide security, balance and traction. Boots like our Dowler Boots, or shoes like the Dunham Derbies in rugged pull-up leather with rubber soles are excellent options to help you navigate snowy or slushy conditions.

Gloves are also a must-have. Wool or leather with a warm lining are always smart choices.

The nippiness of winter can really sneak up on you. So, please take care and follow these tips to Cope with the Cold.


essential spring wardrobe for men

Men’s wardrobe essentials for spring can be as fresh as a daisy.

Spring is a great time of year. The air is warmer, the days are longer, flowers are blooming, birds are singing. Romantic, isn’t it?

But, deciding what to wear can be confusing, It’s not really hot. Not really cold. Not really sure. Hmmm….

1. Pants

Chinos or khakis, jeans and shorts made with mid-weight fabrics, like blended cotton, are all good choices.

2. Shirts

Men’s shirts for spring come in a wide variety of cuts and fabrics which are perfect for the season. Remember, look for materials that breathe and flow, like linen, gingham, cotton or a cotton blend.

3. Sweaters

A nice, lightweight wool or cashmere sweater to throw on when needed is important to have on hand. Lightweight jackets such as a waist-length overcoat, a bomber or denim are also key, as is a gauzy scarf to protect your neck and throat from a springtime chill.

Pack all of your layers in an attractive leather bag, like the Gaston Messenger, which isn’t only practical, it’s beautiful.

Your spring footwear can run the gamut from sneakers like our Geller Trainers in water-repellent suede, to Oxfords, for example the classic Dean Oxfords will help to pull any outfit together. Handsome Roy Loafers also in water-repellent suede make for a fun alternative.


These are the basics, the fundamentals, the must-haves. Don’t be afraid to mix things up. Add some accessories like a bracelet, and don't forget to wear an attractive, dependable belt.

Let your imagination and your own sense of personal style guide you. And, please let us know what you’re sporting in each of these seasons in the comment section below. We all need some inspiration.


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