Thanks to George for joining us for this video and thanks to IWC, one of our favorite watch brands of all time, for helping make this video happen!
Now that we’re headed into Fall it’s about time you start thinking about your sweater rotation. While cashmere is expensive, it’s no longer just a true luxury item, and you can now find cashmere sweaters at multiple different price points. We get asked about cashmere sweaters a ton so we thought it was time we gave you our opinion on whether or not cashmere was worth it.
-Very light, soft, and warm. Cashmere is the ideal material for sweaters.
-They are extremely comfortable and layer easily.
-Have a nice finish that can be dressy or casual.
-Expensive to very expensive.
-Delicate and require extra care. Not as durable as merino wool or cotton versions.
-Cashmere sweaters now come at a huge range of price points so it can be tough to know the quality.
Ashley: Worth It
Dorian: Not Worth It
Building a stylish, versatile wardrobe starts with a solid foundation, and with shirts, you want to find simple, versatile options that are timeless and go with everything. Don’t be afraid to buy multiple colors of the same shirt to take out over-thinking about wardrobe. These are the five essentials shirts that every man should own!
Don’t forget to check out our shirt Fit Guides for more info.
1. White dress shirt
3. Black T-shirt
4. Chambray shirt
5. Solid colored polos
Make sure you have a good rotation of solid-colored polos in basic colors like black, grey, navy, and white.
A henley shirt is only recommended if you have a trim to medium build. If you’re a bigger or athletic guy it’s not the right shirt for you.
White Dress Shirts:
In my previous story, I mentioned that I didn’t like the biker style very much because they have a lot going on and should only be worn if you have a very specific rock and roll style. I still think this is true if you go with the traditional or classic-style biker jacket with the belt, chrome hardware and shiny leather. But, over the years, I discovered a slightly updated version that does away with the belt and replaces the shiny hardware and leather with matte options. Basically, this style of biker jacket removes all the things I disliked about the traditional versions, and now I’ve got to say, I’m much more of a fan.
As for how to wear them, I’d style with a t-shirt or sweater in white, black, or grey, dark wash or black jeans/chinos, and a pair of black boots. If you want to “dress it up” a bit, then pair with a casual collared shirt (leave untucked) in black, green, or burgundy, and some chinos or wool trousers.
$2395 – Burberry leather biker jacket – Burberry consistently makes some of my favorite leather jackets. You’ll pay for it, but if you can swing it, they’re totally worth the price and the fit is incredible. Remember, leather jackets are a BIFL piece.
$420 – AllSaints cargo leather jacket – all the hardware on this jacket is completely blacked out which I always prefer, but is tough to find. AllSaints’ leather jackets are worth the price and for the quality and construction, they’re a steal!
$420 – AllSaints leather biker jacket
$133 – AllSaints dark green shirt – this is the shirt Dorian wore throughout the video. The dark green color and cut of the shirt is super flattering for all shapes and sizes, especially if you’re thin or huskier.
Leather Bomber Jacket
I’ve said it a gazillion times and I’ll continue to say it, over and over again (all these articles feature bomber jackets) – regardless of your age and body type, from super thin to more rotund gentleman, every single man should have at least one bomber jacket in his closet because it’s a super versatile year-round item that can be worn a myriad of ways. Now whether you go with leather, suede or fabric options, that’s up to you. Frankly, I’d have each option, if your budget allows.
As for how to wear a leather bomber jacket, I always like to keep it simple. Pair with a crewneck sweater or t-shirt, dark wash jeans, and sneakers or boots. To make it more formal, I would pair with a white collared shirt, black tie, and wool trousers. The beauty of a bomber is that you can pretty much wear it with any kind of shirt – just pair with chinos, jeans or trousers on the darker side and you’ll never go wrong.
$500 – AllSaints leather bomber jacket – classic, classic, classic.
$500 – AllSaints leather bomber jacket in greyish blue – if you already own black, mix it up with this neutral-like color. Wear how you normally would with a black or brown jacket.
$465 – AllSaints leather and wool bomber – Dorian wore this in my Fall Shoes video and it’s such a sleek take on an all leather jacket. Super timeless and stylish.
The first outfit is a casual one, comprised of a black polo shirt, a well-fitting pair of dark wash jeans and some white low top sneakers. This is a solid casual outfit that will always look great and put together on every man, regardless of your age or body type.
$198 – John Varvatos Collection Hamptons Silk & Cotton Polo Shirt in black or charcoal (Best luxe polo shirt!)
$13 – H&M Polo Shirt Slim Fit in black (**THESE ARE THE BEST POLO SHIRTS!!!!)
$165 – J. Brand Tyler Taper Fit in slate resin (Love that the color, stitching, and hardware are similar color)
$55 – Levi’s 511 Slim Fit Stretch Jeans in dark hollow
$410 – Common Projects Achilles Leather Sneakers in white
$60 – Adidas Originals Stan Smith (colorway: white/white/fairway – Also available @ Footlocker)
$415 – Tom Ford ‘Snowdon’ Sunglasses
IWC Portugieser Automatic Watch
I like to call this outfit ‘dressy casual’ because it transitions well from day to night. Throw on a leather or cotton black bomber jacket with a black t-shirt, dark wash jeans and black leather chukkas.
If you’re thin to average build, you can also wear a white t-shirt. However, if you’re a broader man that’s not in shape, and you decide to take off your jacket, then a white t-shirt will actually spotlight how big you are (and not in a good way). Also, the reason why you want to go with black chukkas is because black is the dominant color in your jacket. I went with leather chukka boots over suede and lace-up boots because the latter options won’t look appropriate for every season.
$670 – All Saints Mower Leather Bomber Jacket in black (LOVE how minimal this jacket is – definitely a BIFL!)
$88 – Everlane Cotton Bomber in black
$60 – James Perse Clear Jersey Crew in black
$10 – H&M Crew-neck T-shirt in black
$170 – Diesel Buster 0607A Tapered Jeans (I’ve bought my fiance 3 pairs of these – they’re that good!)
$55 – Levi’s 511 Slim Fit Stretch Jeans in dark hollow
$175 – Johnston & Murphy Conard Cap Toe Chukka in black
Why a bomber over a blazer?
A bomber is a very stylish, modern alternative to a blazer that works in almost all the same occasions and looks great for every man, regardless if you’re a teenager all the way to a retiree. A younger gentlemen in high school or college, for instance, wouldn’t necessarily need a blazer, so that’s why I’m not recommending it over a blazer. If the occasion does call for a sport coat or blazer, in a pinch, you can use the jacket in my next recommendation and dress it up like I did in the picture below.
Lastly, my classic go-to formal outfit is a charcoal or navy suit with a white semi-spread collar dress shirt, black or charcoal tie, white pocket square, and oxford dress shoes. If you’re going with a charcoal suit, then pair with a black tie and black dress shoes. For a navy suit, pair with a charcoal tie, and dark brown dress shoes.
I love these two suits because it’s very easy to go formal by adding a tie or dress them down by forgoing a tie or swapping in a t-shirt instead of a collared shirt.
$1395 – Burberry Modern Fit Wool Part Canvas Suit (charcoal)
$498 – Brooks Brothers Red Fleece Grey Suit
$115 – TopMan Grey Slim Fit Suit (alternative for warm climates: Topman Charcoal Linen Suit)
$280 – Allen Edmonds Carlyle Plain-Toe Oxfords (black or brown)
$120 – Aldo Bandolla Dress Shoe (black)
$19 – The Tie Bar Grenafaux Tie (My, hands down, favorite solid tie – go with black or charcoal)
$10 – The Tie Bar Solid White Cotton Pocket Square
I love henleys, because they look sexy and masculine, especially when the top 1 or 2 buttons are undone to draw the eyes to your chest and shoulders to show off your physique in a flattering way. Hence, the image below.
BUT, and this is a big mistake I see a lot of men making – they’re not for every everyone. More on that shortly.
Let’s get into what to look for in your henleys based on the time of year.
Generally, henleys will be made out of cotton, so there’s really not much choice outside of that, but you still need to consider fabric weights depending on the time of year. The main thing to know is that lighter weights should be worn in warmer months or in warmer climates and thicker, heavier fabrics in cooler months or climates. You can get them in everything from a lightweight summer weave, where it feels like a t-shirt, to thicker, quilted versions which will keep you warm during the cooler months.
You don’t have to worry too much when buying them because, based on the time of year, the brands will carry the appropriate weights. But I still want you to be aware of it just in case.
Like all your clothing, including henleys, they should have a trim fit throughout the body and arms – no matter your body type. You never want it too loose anywhere because that’s when you’ll look sloppy and not put together. You shouldn’t be able to pinch more than 1-2 inches of fabric on one side of your stomach and no more than an inch around the bicep.
The image below highlights the proper fit around the torso and sleeves.
I mentioned earlier that henleys aren’t for everyone, so let’s get into that right now since we’re talking about fit.
For Thin Gentleman
If you’re a thin guy, no matter your height, if you want to wear a henley, you absolutely need to nail the fit, especially if you’re going to wear a long sleeve version. If the fit is too loose, it’ll make you look thinner and more frail than you are – not good!
I only like long sleeve henleys on thinner men if they’re layered underneath a jacket, like the below right image. When worn on their own, it really spotlights and elongates your thinner torso, like image on the left. So if you’re a thinner guy and want to wear a henley on its own, then wear a short sleeve version since it’ll look similar to your t-shirts.
If you’re a rotund gentleman (aka you’re not in the greatest shape and have a belly), you cannot wear a henley shirt, period. Allow me to show you why and explain. See exhibit A:
Because of the button placket on the front, coupled with the lack of a collar, a henley will shine a massive spotlight on your bigger neck and torso. This is when a polo shirt is perfect and should be used instead, because a polo shirt’s collar will visually keep your torso balanced and in proportion, so your top half doesn’t look so big compared to your bottom half. The image below of James Corden shows a guy with the exact same body type as the image above, but in a polo shirt. Talk about a night and day difference…
Best Ways To Wear A Henley Shirt
For a long sleeve, you would normally wear these during the cooler months as a layering piece, so I styled Dorian in a long sleeve henley shirt underneath a bomber jacket, dark wash jeans, and sneakers.
Burberry Lightweight Lambskin Bomber Jacket
J. Crew Wallace & Barnes Wool Henley Sweater
Diesel Buster 0607A Jeans
Allen Edmonds Decatur Ave Black Dress Belt
Johnston & Murphy Conard Cap Toe Black Chukka
IWC Portugieser Automatic Watch
Ray Ban RB4258 Sunglasses
During the warmer months you can wear them with the sleeves pushed up. As I mentioned in one of my other videos, women LOVE to see sleeves rolled/pushed up around your forearms.
My Favorite Henley Shirts
Here are some great short sleeve and long sleeve (lightweight and heavyweight) henley options that I love.
Short Sleeve Henleys
Long Sleeve Henleys
So let’s go through what you should look for in a Spring and Summer suit and the best shoes to wear during this time of year.
I love brown, green, and burgundy during these seasons, but I’m also a big fan of lighter colors such as: light to medium blues, light greys, and camel.
For bolder colors, like green and burgundy, I prefer that they’re solid because a pattern can be too bold of a look and make you look like a goofball.
Experimenting with patterns is a perfect way to inject some fun and personality into your suits. I love windowpanes, plaids, checks, and stripes (ie. seersucker striped pattern).
It is perfectly fine to wear a darker color, like navy, but I always prefer to go with a navy windowpane or a nice navy plaid suit to help slightly break up the big swath of a dark color.
During this time of year, there’s a lot of fabric choices to choose from – linen, cotton, seersucker, or a lightweight wool fabric.
Most Spring & Summer wool suits will generally be around 8 – 10 ounces, which is your typical year-round fabric weight. I tend to prefer 8-8.5 ounces as that’s a nice lightweight wool that’ll keep you comfortable.
If you live in a more tropical environment that’s hot and humid, I recommend going with fabric that is around 6 ounces, since it will be much lighter and more breathable. Linen is typically a very lightweight, breathable fabric choice although you will have to deal with the immense wrinkles that will accrue throughout the day – there’s just no way around it with linen, unfortunately.
Another really great fabric that doesn’t wrinkle and that’s quiet breathable is seersucker, which I really love. Traditionally, seersucker fabric is blue and white but there are a lot of different color variations these days.
Aside from pattern, this is another area where you can add some flair to your Spring suiting.
There are 3 different hem lengths I recommend:
Exposed ankle – If you want a little bit of your ankle to be exposed than hem pants so they hit the top of your outer ankle bone. Make sure your pants are tapered pretty slim towards the ankle so that there’s not a bunch of fabric flopping around.
No break – When you want to wear loafers, have your pants hemmed so they’re barely skimming the top of your shoes. Again, pants should be tapered pretty slim towards the ankle.
Slight break – More versatile and appropriate for all occasions.
Pairing Your Spring/Summer Suit with Dress Shirts & Ties
For dress shirts, I love using pastel colors like light pink, light green, and sky blue and patterned dress shirts, like gingham and stripes.
For ties, I love polka dots, florals, and fun patterns during this time of year. I also really like using silk knit ties in solid colors since they complement the visually lighter suits. Just please, make sure your ties are proportional to your body type.
If you want to inject some color in your charcoal or navy suit (that you already own), pair it with a gingham or striped dress shirt, or even a lavender or light pink dress shirt. This will help give a more Spring-vibe to your outfit.
If you go with a patterned suit, then make sure to keep your dress shirt and pocket square a solid color because you don’t want to go overboard with mixing patterns. The tie can have a pattern, though.
If you’re wearing a solid Spring colored suit, then gingham and striped dress shirts in pastel colors look really good here. You’ll want a bolder solid colored tie so that it stands out from the shirt and compliments your suit.
If you’ve watched or read any of my other shoe videos and articles, I’ve specifically mentioned that you should save your suede items for Spring and Summer, and guess what? Now it’s time to bring them out.
My 2 favorite shoes to use are suede monkstraps and penny loafers.
The Best Spring/Summer Suits
Lightweight Wool Suit
I love the Brooks Brothers navy plaid suit – it was so easy to style it in a couple different ways on my friend Jordan O’Brien from The Gentlemen’s Cove.
$490 – Brooks Brothers plaid suit
$300 – Topman Dark Brown Suit
The Burberry and J.Crew gingham print suit are incredible and will make a stylish statement this Spring!
$1995 – Burberry Linen silk suit
I’ll be updating this section soon as more seersucker suits hit the stores.
My Top 10 Men’s Spring Essentials
1. Lightweight, Spring Suit
Whether you go with a linen, cotton, seersucker, or lightweight wool suit, these options will make a statement and keep you cool throughout the Spring and Summer months.
2. Linen or Lightweight Blazer
These lightweight blazers are perfect for casual Fridays at work or heading to lunch or dinner with friends. They’re a great way to insert a stylish statement while keeping cool. Linen will wrinkle a bit, but that’s part of its character so embrace it.
3. Gingham Button Up Shirt
I love gingham shirts for the Spring because they can be worn dressed up with a suit or blazer or dressed down on their own or underneath a sweater. I included some great lavender, navy, and light grey gingham options below.
4. Silk Knit Tie
There’s no other brand that I love more than The Tie Bar. The quality, construction, and color/pattern choice can’t be beat by any other brand. Like I’ve always said, they’re not paying me to say this.
5. Polo Shirt
Polo shirts instantly make an outfit look more put together and Spring is the perfect time to start wearing them. I like John Varvatos, but be careful if you’re not in shape or have erect nipples because their silkier shirts will highlight these areas. The fit on Theory and Fred Perry polos is excellent and H&M is my go-to when I’m more price-conscious. You’ll need to replace those roughly every 8 weeks though due to fading.
6. Short Sleeve Button Up Shirt
Not only do short sleeve button-up shirts look stylish, but every man (regardless of age or body type) can wear these. There’s currently so many great options from J.Crew and come March/April, Topman will have an equally great selection.
$480 – Prada Slim Fit Star Print Cotton Poplin Shirt
$128 – Todd Snyder Short Sleeve Floral Print Shirt
$60 – J.Crew Short-Sleeve Shirt in Jungle Print
$60 – J.Crew Short-Sleeve Oxford Shirt in Blue
$60 – J. Crew Short-Sleeve Shirt in Striped Heather Poplin
$55 – TopMan Blue Abstract Print Short Sleeve Casual Shirt
7. Suede Bomber Jacket
I’ve maintained in some of my other videos and articles that you should save your suede for Spring. Well, it’s time to break out those items. I love the options below – you can choose from navy, light grey, and brown suede jackets. The A.P.C. jacket is a BIFL piece and will never go out of style.
8. Penny Loafers
Finally we’re entering ankle season, which means penny loafers can finally be worn. I love Ferragamo’s loafers (I got a pair for my fiance Dorian 2 or 3 years ago) and they’re totally worth the price because they definitely hold up and still look great after years and years of wear.
9. Suede Monkstraps
Suede monkstraps, whether you get a dark brown, grey, or navy pair, can just take an outfit to another level. It’s such a stylish touch to any outfit and can be worn with a suit, chinos, or jeans. Make sure to Scotch Guard them before you wear them for the first time – always gotta protect your suede items!
$698 – Brooks Brothers Navy Suede Double Monk Strap
$398 – Brooks Brothers Suede Double Monk Strap Shoes
$275 – Crosby Square Conley Double Monk Strap Shoe (Espresso and Navy)
$80 – H&M Suede Monkstrap Shoes
Chinos should only be worn in Spring, Summer, and early Fall and that’s it. They’re a great alternative for those days when you don’t feel like wearing jeans and when you want to just feel cool and comfortable.
Jordan’s 10 Men’s Spring Essentials
These as well as other great alternatives were included in my Summer Essentials E-Book. A lot of Jordan’s picks I actually included in that e-book so be sure to check it out if you haven’t already 🙂
2. Linen Suit
Linen, as well as the other lightweight fabrics I also included in my list, is very breathable and will keep you cool during the warmer months. Here are some of my favorite items currently available.
3. Panama Hat / Straw Fedora
Whether you need some extra sun protection or want to look stylish while staying cool, straw hats are super breathable and lightweight. Every year I get J.Crew’s panama hat, but it only lasts the season before it starts to fall apart. I’m currently eyeing Loro Piana, Brooks Brothers and Stetson’s hats because I know I can count on the quality and construction.
$735 – Loro Piana Laurence Straw Panama Hat
$298 – Brooks Brothers Straw Fedora
$287 – Lock and Co Napoli Hat
$105 – Stetson Men’s Centerdent Fine Panama Hat
$65 – J. Crew Paulmann panama hat with striped band
4. Basic Striped T-Shirt
Striped t-shirts are super easy to insert into your current wardrobe. They look great with your suits, blazers, bomber jackets or just on their own.
$90 – Todd Snyder Slim-Fit Striped Cotton T-Shirt
$88 – Todd Snyder Fine Stripe Button Pocket T-Shirt in Maroon
$60 – J. Crew Wallace & Barnes Indigo T-Shirt in Stripe
$45 – J. Crew Garment-Dyted T-Shirt in Microstripe
$35 – TopMan Selected Homme Navy and Off White Stripe T-Shirt
5. Long Sleeve Henley Shirt
I like long sleeve henleys when they’re worn as a layering piece, so underneath a casual button down shirt paired with some dark wash jeans and boots or sneakers. If you’re a slim or wider gentleman, I highly advise against wearing henleys on their own because they emphasize your body size even more (and not in a good way).
6. Denim Jacket
If you’re new to wearing denim jackets, I suggest going with a black or dark grey version because it’ll be a lot easier to wear, especially if you wear jeans a lot because you don’t want to look like you’re wearing a Canadian tuxedo.
7. Lightweight Jacket
On those windy or rainy days, having a lightweight jacket that can combat the elements while looking stylish is always what I strive to find.
$280 – Saturdays Travis Windbreaker (Sage or Clay)
$200 – J. Crew Field Mechanic Jacket
$160 – Under Armour Sportswear Meters Panelled Shell Hooded Jacket
$40 – Uniqlo Lightweight Packable Hooded Jacket
8. White Sneakers
I have a whole video and article dedicated to white sneakers because I truly believe every man, regardless of age or body type, should own a pair.
9. Classic Timeless Pair of Sunglasses
Be sure to check out my Sunglasses story for specific options I recommend based on your face shape.
10. NATO Strap
Interchanging your watch straps is an easy way to insert some fun and personality into your outfit.
Here’s a great place for straps that I love – these are my favorite for Spring:
$8 – Navy Perlon Nato Strap
$8 – Navy and Grey Nato Strap
$8 – Dark Brown Perlon Strap
$8 – Grey Perlon Strap
$9 – Black, Red, And Green “JAMES BOND” PVD Nato Strap
As far as watches go, see my Watch article/video.