3 Outfits Every Guy Needs

My articles and videos almost always center around a specific piece of clothing or accessory, so I thought it would be fun to switch it up and talk about 3 head-to-toe foundational outfits every guy needs. Once you have these 3 outfits, you can build an entire wardrobe around them. And here’s the beauty of them: from these 3 outfits, you can switch things in and out to add your own personal touch and truly make them your own.

Outfit 1

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.

3-Outfits-Every-Guy-Should-Own-Ashley-Weston-1

$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

Outfit 2

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.

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$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.

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Outfit 3

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.

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$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

POTW: Johnston & Murphy Burgundy Cap Toes

I was prepping for a fitting, and I came across these Johnston & Murphy burgundy cap toes that I thought you should know about. I’m not normally a fan of burgundy shoes because I often find the color to be difficult to wear and usually ends up being too much of a statement piece. But, these are different because the darker color is closer to a burgundy brown instead of the more reddish-oxblood color you often see with other “burgundy shoes” and that makes them much easier to wear. So, I had to make them my pick of the week!

 

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$155 – Johnston & Murphy Burgundy Conard Cap Toe 

Best Ways to Wear

The decorative broguing along with the brown soles adds a casual look to them making them easy to wear with your summer suits, like a green or navy cotton suit, or with some chinos or dark wash jeans. Blues, greens, and khaki go great with burgundy. If you’re ever unsure how to wear these, just know that whenever you wear brown dress shoes with a more casual outfit, you can easily wear these instead.

I also want to address the contrasting stitching. On more formal shoes it can be very distracting and pull the attention away from your outfit and really focus it on the shoes. But on a casual dress shoe, such as these, it works because you’re never going to be wearing them with a really formal outfit. So if you’re thinking about doing that, then please don’t.

Like I’ve said before, accessories are a great way to add some fun touches to your outfit and these shoes do exactly that.

BurgandyCapToeOutfits_AshleyWeston

 

Look 1

$40 – J. Crew Slub Cotton Deck-Striped T-Shirt
$68 – J. Crew Navy or Green Stretch Chino Pant in 770 Fit
$30 – Uniqlo Slim Fit Flat Front Chino in Navy

Look 2

$69 – Brooks Brothers Selvedge Oxford Sport Shirt
$70 – Levi’s 511 Slim Fit Stretch Jeans (in blue flame, dark hollow and stump town)
$228 – JBrand Tyler Fit in Blue Hood

Look 3

$358 – J. Crew Ludlow Suit Jacket in Italian Cotton Oxford
$188 – J. Crew Ludlow Suit Pant in Italian Cotton Oxford
Shirting – See my dress shirt article
Ties – See my ties article

16 Accessories Every Man Needs

These are, to me, the 16 accessories every guy needs to own, regardless of your age, occupation, and lifestyle. Some of these items you may not wear often, but there will be an occasion, as a grown man, when you will need them and you’ll be thankful that you thought far enough ahead to take care of them before it’s too late and you’re scrambling at the last minute. I’ve also included my favorites for each of these items below. But these points below are just skimming the surface compared to the much more through Men’s Essential Accessories Series I did recently.

Have questions? Curious what others think?

Join us in the comments section of the video above.

16. White Pocket Square

Like I’ve mentioned before, every man should have at least a grey suit. Even if you only wear it once every year, you’re going to need a suit. Along with that, looking well dressed is always about the details and a white pocket square is an easily overlooked item that really does make a big impact and it’ll only set you back a couple of bucks.

White Pocket Square Ashley Weston

$175 – Tom Ford Solid Classic Silk Pocket Square
$60 – Boss Solid Silk Pocket Square
$10 – The Tie Bar Solid White Cotton Pocket Square

15. Silver Tie Bar

This is another overlooked item. I talked about this in my article about the 12 Things Men Wear That Women Love, but a tie bar is something that adds that special touch to your outfit. It’s also so cheap to own so order it once and you’ll never think about it again.

Silver Tie Bar Ashley Weston$15 – The Tie Bar Silver Shot Tie Bar
$70 – J. Crew Sterling-Silver Tie Clip 

14. Solid Black and Navy Tie

These two ties will work for any suit you have in your closet, making them an absolute must have. Make sure the width of your tie complements your body type.

Black and Navy Tie Ashley Weston

$19 – The Tie Bar Grenafaux Tie (available in black and navy)
$60 – J. Crew American Wool Navy Tie
$60 – J. Crew American Wool Black Tie

13. Dress Socks

Get rid of your white socks. These socks can and should be worn as your everyday socks. If you need heavier duty, thicker socks for your job or because of the weather, there are plenty of companies that offer warmer versions.

Solid or Patterned Dress Socks Ashley Weston

$4 – Uniqlo Argyle Socks
$20 – Brooks Brothers Egyptian Cotton Jersey Knit Crew Socks
$15 – J. Crew Tipped Microstriped Socks

12. Sunglasses

Whether you’re a sunglass man or not, sunglasses are important because they’re going to protect your eyes from the sun, prevent you from squinting, which creates wrinkles around your eyes, and they can add a stylish, cool touch to your outfit. Check out my sunglasses story so you choose the right frames for your face shape.

Sunglasses 1 Ashley Weston 2

$415 – Tom Ford Snowdon Sunglasses
$98 – J. Crew Jack Sunglasses
$95 – Warby Parker Winston Sunglasses 

11. Baseball Hat

We all have those lazy days, myself included, where you just say F it, I’m gonna throw on a hat. When it comes to baseball hats I have very specific opinions about them so I shared some of my recommendations below.

Baseball Cap Ashley Weston

$48 – Gents ‘The Directors’ Baseball Cap
$22 – Flexfit Blank Snapback 2014

10. Black and Brown Oxford or Derby Shoes

Not only do these oxford dress shoes look great with your suit, but they also look nice with chinos, jeans, and trousers when you want to dress up a more casual outfit.

Black and Brown Shoes Ashley Weston

$395 – Allen Edmonds Carlyle Plain-Toe Oxfords
$750 – Prada Plain-Toe Bluchers
$175 – Johnston & Murphy Melton Cap Toe Oxfords

9. Black and Brown Dress Belts

Since you’re going to own dress shoes, you absolutely need to match your leather belt to your shoes.

Black and Brown Dress Belt Ashley Weston

$98 – Brooks Brothers Leather Dress Belt
$98 – Allen Edmonds Poplar Dress Belt
$25 – H&M Leather Belt

8. Weekender Bag

Everyone travels. Whether it’s to some exotic country, or across town, you’ll need to put your clothes in something AND trash bags are not an option. Like every accessory you own, it should not only serve it’s purpose, but look damn good at the same time. I have a whole article about weekender bags you should check out.

Weekender Bag Ashley Weston$965 – Frank Clegg Signature Travel Duffle (in black, chocolate or chesnut)
$800 – Killspencer Weekender 3.0 (in black leather or charcoal grey leather)
$115 – Everlane ‘The Dipped Weekender’ (in black/black, navy/black or reverse denim/black)

7. Dopp Kit

This item goes great with your weekender bag. Again, doesn’t matter if you’re traveling to another city or to the gym, a dopp kitt is essential because it’ll keep your grooming products organized and contained in a respectable manner.

Dopp Kit 1 Ashley Weston 2

$148 – Jack Spade Mason Leather Zipper Top Dopp
$300 – Shinola Travel Kit
$200 – This is Ground Tech Dopp Kit

6. Backpack or Briefcase with Detachable Strap

Depending on what you do for a living, if you live a more casual lifestyle or you’re a student, then a backpack is great. If you are in a more professional environment, a briefcase is best.

Backpack Briefcase Ashley Weston 1

Backpack

$800 – This is Ground Venture Regular Backpack
$210 – Cõte & Ciel Rhine Backpack
$120 – Aer Fit Pack Backpack 

Briefcase

$990 – Frank Clegg Zip-Top Briefcase
$895 – Shinola Slim Briefcase
$325 – Uri Minkoff Pebbled Leather Fulton Briefcase 

5. Casual or Dress Watch

Like the last point, which one you go with will depend on your lifestyle. Whether you’re a watch guy or not, any self-respecting man should own a watch or two.

Casual and Dress Watch Ashley Weston

Casual Watch

$7,000 – Rolex Submariner 114060
$3,400 – Omega Speedmaster Professional Moonwatch
$375 – Orient Diver Mako USA II

Dress Watch

$12,700 – IWC Schaffhausen Portugieser Automatic
$532 – Hamilton Intra-Matic Silver Dial Leather Watch
$195 – Tissot T-Classic Tradition Silver Dial

4. White Low Top Sneakers

Everyone has casual days, and white sneakers look so sharp on every guy regardless of your age or body type. If you’re really scared of wearing white, or think that it doesn’t look right, ease yourself into it with a nice low top lace-up black or navy sneaker.

White Sneakers 2 Ashley Weston

$370 – Acne Studios Adrian White Leather Sneakers
$75 – Adidas Stan Smith Sneakers
$65 – Converse Jack Purcell Classic Low Top

3. Boxer Briefs

All women find boxer briefs, specifically darker colors, so sexy on a man. And all men should be wearing them. Period.

Boxer Brief Ashley Weston

$26 – Exofficio Give-N-Go Boxer Brief
$13 – H&M 3-pack Boxer Shorts
$6 – Uniqlo Supima Cotton Boxer Briefs

2. Black and Brown Casual Leather Belts

Whenever you’re wearing jeans, chinos or shorts, throw on a casual leather belt because it’ll add a visually nice touch to your outfit.

Black and Brown Casual Belts Ashley Weston

$98 – Allen Edmonds Sun River Casual Belt
$295 – Salvatore Ferragamo Reversible Leather Belt 
$18 – H&M Leather Belt

1. A Quality Wallet

The things a man carries tells a lot about him and that’s no more true than with your wallet – check out my  article to the left for bifold, card cases, and phone wallet recommendations.

The below are only a few recommendations for bifold wallets.

Wallet Ashley Weston

$195 – Shinola Slim Bifold Leather Wallet 
$525 – Louis Vuitton Slender Wallet
$80 – Bellroy Low Down Wallet

Top 4 Shoes For Spring Men

Top 4 Men’s Shoes for Spring

These are the top 4 men’s shoes for Spring that I really love. You’re probably not going to wear these with your Fall and Winter wardrobe, so it’s time to pull these shoes out of your closet and let them shine! Footwear is a great way to inject new life in your existing wardrobe, and these 4 shoes will make a stylish statement during Spring and Summer. 

Here are my top 4 favorite shoes for Spring:

4. Suede Double Monk Straps

I included these in my Top 10 Essential Items for Spring as well. 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!

 

$685 – Crockett & Jones Lowndes Espresso Calf Suede
$398 – Brooks Brothers Suede Double Monk Strap
$275 – Crosby Square Conley Double Monk Strap (Espresso and Navy)
$80 – H&M Suede Monkstrap Shoes

3. Penny Loafers

I absolutely love penny loafers. They look so good when worn with no-show socks and a little bit of ankle exposed. Whether you cuff your jeans or chinos, or hem your pants so there’s no break or a little ankle showing. A leather loafer looks so chic and luxurious. I love Ferragamo’s loafers (I got a pair for my fiancé 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.

Penny Loafers

$760 – Ferragamo Penny Loafer Shoe
$185 – Johnston & Murphy Stratton Penny

2. Suede Driving Shoes

Think of them as the middle ground between sneakers and penny loafers. They’re just as comfortable as sneakers, yet dressier like a penny loafer. I also included these in my Men’s Summer Essentials ebook because they work during the warmer months in general.

My hands down, favorite suede driving shoe is from Tod’s. Everything about that shoe – construction, design, and color choice – is so damn sexy and incredible. It’s worth every penny, and there is no close second for me.

 

$475 – Tod’s Gommino Driving Shoe (in brown, navy, and grey)
$115 – Jack Erwin Parker Driving Loafer (in navy, chocolate, caramel)

1. Navy or Grey Sneakers (Canvas or Leather)

Outside of your white sneakers, I love a great navy or grey low top sneaker. They’re neutral colors so you can wear them with everything you have and they definitely won’t get dirty quickly.

If you want to splurge, Common Projects makes my favorite sneakers and a close second are by Lanvin.

 

$570 – Lanvin Shiny Cap Toe Sneaker (in navy or grey)
$509 – Common Projects Achilles Low Premium in Grey (or navy suede)
$75 – Converse JP Jack Sneaker (leather)
$65 – Converse Jack Purcell Ox Sneaker (canvas)

Spring & Summer Suit Guide

There’s going to be some items in your closet that’ll need to transition for the Spring and Summer seasons, and that definitely includes your suits. If you’ve seen my other suiting articles and videos, then there’s some suits that’ll work year round, but there’s always room for some seasonal specific suits.

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.

 

Colors

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.

Patterns

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.

Fabric

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.

Hem

pants - hem break - ashley weston
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.

Pro Tips

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.

Shoes

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

Linen

The Burberry and J.Crew gingham print suit are incredible and will make a stylish statement this Spring!

$1995 – Burberry Linen silk suit

$546 – J.Crew Ludlow Gingham Linen-Cotton Suit

$150 – H&M Linen blue suit (see matching pants here)

Seersucker

I’ll be updating this section soon as more seersucker suits hit the stores.

$498 – Brooks Brothers Seersucker Suit

Cotton

$2795 – Ermenegildo Zegna Cotton Suit
$456 – J.Crew Ludlow Italian Chino Khaki Suit (and matching pants here)

 

Top 10 Men’s Spring Essentials

There’s only a few weeks of Winter left, so pretty soon we’re all going to have to start thinking about transitioning to our Spring wardrobe. So in addition to your year-round Men’s Essential staples that are already in your closet, Jordan O’Brien from The Gentlemans Cove and I each came up with a list of 10 Spring Essentials that every man should own.

 

 

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.

Lightweight Suit Ashley Weston

$650 – J. Crew Ludlow Geyser Grey Italian Wool Suit
$500 – Brooks Brothers Red Fleece Navy Windowpane Suit 
$300 – TopMan Dark Brown / Burgundy Suit 
$105 – H&M Dark Green Cotton Stretch Suit

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.

Lightweight Blazer Ashley Weston 1

$400 – Suitsupply Havana Green Check Sportcoat
$358 – Brooks Brothers Windowpane Linen Sportcoat
$168 – J.Crew Unstructured Ludlow Cotton-Linen Blazer
$99 – H&M Linen-Blend Navy Blazer  

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.

Gingham Button Up Ashley Weston

$450 – Ralph Lauren Purple Label Aston Gingham Dress Shirt 
$88 – J.Crew Ludlow Navy Gingham Shirt
$80 – Banana Republic Grant Fit Silver Gingham Shirt
$55 – The Tie Bar Grey Gingham Shirt

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.

Silk Knit Tie Ashley Weston

$25 – The Tie Bar Scramble Knit Blue Polkas
$25 – The Tie Bar Knit Strip Brown
$25 – The Tie Bar Knitted Wine
$25 – The Tie Bar Midnight Navy

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.

Polo-Shirt-Ashley-Weston-Mens-Clothing-Fit-Guide $198 – John Varvatos Collection ‘Hampton’ Silk & Cotton Polo Shirt
$95 – Theory Cotton Polo
$85 – Fred Perry Navy/White Tipped Polo Shirt
$13 – H&M Polo Shirts

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.

Short Sleeve Button Up Ashley Weston $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.

Suede Bomber Jacket Ashley Weston$1,455- A.P.C. Louis W Suede Bomber Jacket
$1,085 – Hackett Mayfair Suede Bomber Jacket
$160 – TopMan Light Grey Faux Suede Formal Bomber Jacket
$160 – TopMan Faux Suede Formal Bomber Jacket

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.

Ferragamo Penny Loafer 2 Ashley Weston$760 – Ferragamo Penny Loafer Shoe
$195 – Jack Erwin Archie Penny Loafer Hazelnut
$185 – Johnston & Murphy Stratton Penny

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!

BB Suede Monk Straps Ashley Weston$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

10. Chinos

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.

Chinos Ashley Weston$575 – Maison Margiela Cotton-Twill Chinos
$75 – J.Crew Broken-In Chino in 484 Fit
$30 – Uniqlo Slim Fit Chinos
$30 – H&M Chinos Skinny Fit

Jordan’s 10 Men’s Spring Essentials

1. Huaraches

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 🙂

Huaraches Ashley Weston $165 – Vintage Artisan Classico Brown
$88 – Chamula D.F. Dk. (Brown or Navy)
$88 – Chamula Cancun with Natural Crepe Sole

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.

Linen Suit Ashley Weston$2,000 – Burberry Slim Fit Wool Silk Linen Three-Piece Part-Canvas Suit
$349 – Brooks Brothers Milano Fit Check Linen Suit
$99 – H&M Linen-Blend Suit Jacket
$50 – H&M Linen-Blend Suit Pant 

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.

Panama Hat Ashley Weston 1$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.

Stripe Tshirt Ashley Weston$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).

Long Sleeve Henley Shirt Ashley Weston$150 – Rag & Bone Slim-Fit Mélange Cotton-Blend Jersey Henley T-Shirt
$59 – L.L. Bean Signature Slub Henley
$39.50 – J.Crew Slim Broken-In Henley

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.

Denim Jacket Ashley Weston$295 – Rag & Bone Standard Issue Washed-Denim Jacket
$195 – All Saints Mens Hockett Denim Jacket
$90 – Levi’s The Trucker Jacket (in rinse or lamar black stretch)
$40 – H&M Denim Jacket

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.

Casual Jacket Ashley Weston$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.

White-Sneakers-Ashley-Weston-Mens-Wardrobe-EssentialsHeader$100 – Nike Tennis Classic Ultra
$75 – Adidas Originals Stan Smith Sneaker
$65 – Converse ‘Jack Purcell’ Classic Low Top Sneaker

9. Classic Timeless Pair of Sunglasses

Be sure to check out my Sunglasses story for specific options I recommend based on your face shape.

Rayban Wayfarer Ashley Weston$325 – Oliver Peoples L.A. Coen Sun
$140 – Ray Ban RB2132 58 New Wayfarer
$95 – Warby Parker Barkley Sunglasses
$95 – Warby Parker Beckett Sunglasses

10. NATO Strap

Interchanging your watch straps is an easy way to insert some fun and personality into your outfit.

NATO Strap Watches Ashley Weston

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.

Spring/Summer Suede Jacket Outfit

I came across this image that I thought would be a perfect Spring & Summer men’s suede jacket outfit because it’s a great, casual everyday outfit that you can wear when you’re going out with friends or if you work in a casual work environment. It has the added benefit of being able to be dressed slightly up or down as well as layered depending on the weather.

 

Jacket

A suede jacket is perfect for Spring and Summer and will look great on every guy, regardless of age or body type. But if you’re not into suede, or like other styles, look no further than the Harrington jacket or a wool bomber jacket.

$1,455- A.P.C. Louis W Suede Bomber Jacket
$1,085 – Hackett Mayfair Suede Bomber Jacket
$160 – TopMan Faux Suede Formal Bomber Jacket

Shirts

The plaid shirt underneath the grey sweater can be switched out for your classic white or blue oxfords or other fun colors or patterns like navy and/or green plaid or gingham.

$188 – J. Crew Albiate 1830 Ludlow shirt in red plaid
$139 – Steve Alan Masters Shirt
$92 – Brooks Brothers Non-Iron Milano Fit Mini-Madras Sport Shirt
$85 – TopMan SELECTED HOMME Navy And Grey Check Button Down Shirt

Crewneck Sweaters

On warmer days, you can ditch the crewneck sweater and just wear a collared shirt.

$298 – Brooks Brothers Golden Fleece 3-D Knit Fine-Gauge Merino Wool Crewneck Sweater
$158 – J.Crew Lightweight Italian Cashmere Crewneck Sweater (in heather dove)
$40 – TopMan Grey Ripple Textured Raglan Slim Fit Sweater 

Chinos

As for chinos, Spring and Summer is when you pull these bad boys out or you can swap them for a pair of dark wash jeans as well.

Make sure, that you know how either your chino pants should fit or how your jeans should fit, based on your body type.

$75 – J.Crew Broken-In Chino in 484 Fit
$30 – Uniqlo Slim Fit Chinos
$30 – H&M Chinos Skinny Fit

Shoes

Lastly, the brown suede chukka boots in the image are great, but you can also swap them out for brown monkstraps or even white sneakers.

$225 – Vince Camuto Branx Two-Eye Chukka 
$175 – Johnston & Murphy Conard Cap Toe Chukka 
$75 – Aldo Granges Chukka

Wool Blazers & Sport Coats

I’m sure you’ve already seen my article/video about a Navy Wool Blazer in my Wardrobe Essentials Series, riiiiiggghhht? If not, then please read and watch it first before we talk about Fall and Winter wool blazers/sport coats, because I’m going to assume we’re on the same page in regard to the differences between a blazer, sport coat and suit jacket as well as how your blazer should fit your body type as well as the finer details of what to look for in a quality blazer. Otherwise, you will probably be lost or think this article is a little anemic. There will be a few critical differences between your year-round blazers and your specific Fall and Winter wool blazers. So let’s get into them.

1. Fabric Weight

The most important difference during this time of year is the fabric weight of your blazer.

You want a much heavier wool fabric, like Harris Tweed, for three reasons:

  1. It will keep you much warmer during this time of year.
  2. The heavier weight pairs better with similar weighted fabrics during this time of year – Like your wool ties and pocket squares, wool trousers, sweaters, cardigans, etc.
  3. If it has a tighter weave, like Harris Tweed, it’ll be more durable, robust and repel water and snow better.

To get technical for a moment, a typical weight you should look for is around 12 ounces, but you can go all the way up to 16 to 20 ounces. For year-round wool blazers, I prefer a fabric weight of between 8 to 10 ounces, depending on your climate. In comparison, for hotter climates/seasons, I usually go with somewhere around 6 ounces for the fabric weight.

You’ll instantly notice the difference of fabric weights when you feel the blazer in-person. It’s a little harder to see it in in pictures, so I would suggest going to a store that carries suits to see it for yourself.

Long story short, you want a thicker wool for this time of year.

2. Color

The second difference is the colors for the time of year. Unlike the year-round wool blazers, this is the time of year where you can wear richer, more jewel-toned colors, all based on your skin tone, of course.

The best way I can describe colors is to think of the leaves changing to their fall colors and those are the colors you want for the season. So that typically means these colors:

  • Browns
  • Burgandys
  • Greens
  • Blues
  • Oranges

I went over all these colors and how to wear them based on your skin tone in my introduction article & video to this series.

3. Patterns

The last and final thing to consider for your Fall & Winter wool blazers are the patterns. Since you’ll be wearing heavier items, bold and heavier patterns work great this time of year.

My favorites are:

All of these patterns are included in my selects from various brands below.

Best Ways To Wear A Wool Blazer During Fall & Winter

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H&M Dark Khaki (Green) Blazer
J.Crew Cotton-Cashmere Crewneck Sweater in Jacquard
The Tie Bar Kingsley Attune
H&M Wool Suit Pants
Aldo Acerrassi boot
Rolex Submariner Date
Tom Ford Snowdon Sunglasses

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Topman Light Brown Wool Rich Formal Coat
The Tie Bar Chambray Shirt 
The Tie Bar Wentworth Plaid 
The Tie Bar Kingsley Attune Pocket Square 
The Tie Bar Metallic Navy Tie Bar
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Johnston & Murphy Cormac Double Buckle Monk Strap
John Varvatos Prince Sunglasses

MensFallWinterEssentialsWoolBlazerAshleyWeston-12

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H&M Wool-Blend Blazer Slim Fit
Brooks Brothers Milano Spread Collar Dress Shirt
The Tie Bar Score Check Tie 
The Tie Bar Olive Green Tie Bar
The Tie Bar Southeast Plaid Pocket Square
Diesel Buster 0607A Jeans
Allen Edmonds Poplar Dress Belt
Allen Edmonds Strand Cap-Toe Oxfords with Dainite Rubber Sole
IWC Portugieser Automatic Dress Watch
Tom Ford Snowdon Sunglasses 

All of these blazers are from companies that I love. Zegna, Canali, and Brooks Brothers’ blazers have superior construction and the fit, color, and pattern are exactly what I look for in a standout blazer for my clients. For more budget-friendly options, I really like J.Crew’s english tweed sportcoats. The weight of these blazers are perfect and the solid textured colors (brown, grey, and navy) will never go out of style. For a nice camel or dark green blazer, Topman and H&M, respectively, make these nice blazers. The fabric isn’t as thick as I’d prefer, but the price point is hard to beat so I’m willing to overlook that.

$2,895 – Ermenegildo Zegna Windowpane Two-Button Sport Coat
$1,595 – Canali Tic Two-Button Sport Coat
$538 – Brooks Brothers Milano Fit Multi-Windowpane Sport Coat
$418 – Brooks Brothers Fitzgerald Fit Blue Harris Tweed Tic with Windowpane Sport Coat
$350 – J. Crew Ludlow Legacy Blazer in American Wool
$220 –Topman Light Brown Wool Rich Formal Coat
$200 – TopMan Selected Homme Navy Blazer
$70 – H&M Dark Khaki Blazer