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.

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$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: What to Wear When Going To The Gym or Airport

I’ve been getting a lot of questions and emails from you about what to wear when going to the gym or airport so you’re still stylish, yet comfortable.

Thus, my POTW are John Elliott’s grey sweatpants because they’re the only item you need to add to your closet in order to create this sharp outfit below. You should already have three out of the four items if you’ve been following my Men’s Wardrobe Essentials Series for any length of time.

John Elliot Sweatpants POTW Ashley Weston

Here’s why this outfit is great:

Sweatpants

I love John Elliott’s clothes because he always does such a great job with creating high quality basics and these sweatpants are no exception. The construction and fabric choices are a cut above the rest, so if you’re able to swing it, I highly recommend these.

$190 – John Elliot Grey Escobar Lounge Pants (also in black)
$40 – Topman Grey Peached Skinny Joggers 

T-Shirt

You already should own a navy, black, and/or white t-shirt. These colors are perfect for the gym because they won’t show your sweat prominently like a grey tee will. Also, they look great with this outfit outside of the gym as well.

$80 – John Elliott Mercer T-Shirt
$30 – Armani Exchange Pima Crew

Jackets

Next, you should also already have a bomber jacket, whether it be navy or black, in your closet because as I’ve said before, bombers look great on every man, regardless of your age or body type. You can easily switch out the bomber for a zip-up hoodie if you want, but I wouldn’t change a single thing in this outfit.

$610 – Ami Navy Twill Bomber Jacket
$80 – Zara Technical Bomber Jacket 

Shoes

And finally, add some white tennis shoes or athletic sneakers from your closet to complete the look.

$120 – Nike Roshe Flyknit 
$75 – Adidas Stan Smith Sneakers

 

 

Lightweight Wool Spring and Summer Jacket

POW: Lightweight Wool and Cotton Jacket

Last Sunday I was getting a client ready for the Oscars, and a friend of his was wearing this incredible lightweight wool jacket that I knew I had to share with you. It’s been quite awhile since a jacket got me this excited.

There’s several reasons why I love this jacket for Spring and Summer, or year-round if you live in a warmer climate: lightweight wool and cotton fabric, incredible construction, texture and color, and its so damn stylish. Normally, I’m not a fan of pockets on the front of a jacket for all body types, as they can add bulk and throw off your proportions if you’re a thinner guy, but, as you’ll see in the video above, these pockets blended in so seamlessly that it isn’t an issue at all.

Wear it with a t-shirt, jeans, and sneakers or dress it up with a collared shirt, wool trousers, and dress shoes – it will go with most casual and dressy casual outfits. Yep, this jacket is that good.

Apolis Indigo Wool Chore Jacket

Jacket

I went into the store and had my friend Michael, who’s average height but a broad build, and Dorian, who’s 6’3″ and slim, try the jacket on and they both looked great in it. See the video above to see what I’m talking about. Also, Dorian ended up picking up the blazer version of the Chore jacket for himself.

$278 – Apolis Indigo Wool Chore Jacket

How To Wear It

Crewneck Sweater

$158 – J.Crew Lightweight Italian Cashmere Crewneck Sweater  (in Heather Dove)
$122 – Life After Denim Lacrosse Crew
$40 – TopMan Grey Ripple Textured Raglan Slim Fit Sweater

White T-Shirt

$60 – James Perse Short Sleeve Crewneck
$10 – TopMan White Slim Fit T-Shirt

Jeans

$228 – JBrand Tyler Taper Fit in Rasalas
$70 – Levi’s 511 Slim Fit Stretch Jeans (Blue Flame or Dark Hollow)

Sneakers

$509 – Common Projects Achilles Low Premium 
$65 – Converse Jack Purcell Classic Low Top (in White or Black)

 

21 Things Men Should Never Wear

In this video, I talk about the 21 things men should never wear! These are the things that’ll curl your toenails, and offend even your grandmother. Just don.do.it.

 

1. Gaudy Rings & Pinky Rings

2. Too Much Cologne
Too Much Cologne Ashley Weston

3. Socks with Sandals

4. Sandals In General

5. Shorts That Go Past Your Knees

6. Old dirty shoes
Dirty Shoes Ashley Weston

7. Cartoon printed boxers

8. T-Shirts with Brand Logos

9. Baggy, Ill-Fitting Clothing

10. Tank Tops
Tank Tops

11. Skinny Jeans

12. Pointy & Square-Toed Shoes

13. Deep V-Neck T-Shirts
Vneck

14. Big, Square, or Monogrammed Belt Buckles

15. Leather Bracelets

16. Elongated Shirts

17. Soul Patch
Soul Patch Ashley Weston

18. Crocs

19. Earrings and Facial Rings

20. Short-Sleeve Sweaters

21. Dress Shoes with Tennis Shoe Soles

THE #ASKAW SHOW: EPISODE 09 W/ Andrew Snavely FROM PrimerMagazine.com

In this episode, my special guest – Andrew Snavely from PrimerMagazine.com answer some of the most scintillating questions for the readers/viewers.

Have a question you’d like me to answer? Ask in the comments of the above youtube video or send me an email.

In this episode, we answer:

Q: I’ve lost a significant amount of weight and now all of my clothes are clownishly large on me. Can a tailor make my clothes fit again or should I just buy all new ones?

A: See the video above for the answer and my men’s clothing fit guide for how your clothes should fit.

Q: I watched your T-Shirt video and if I have a nice looking tee with a pretty minimalist design, does that hinder a look the same way a straight up graphic tee would?

A: Short answer – sort of. See the video for the longer answer.

Q: As a shorter man (5’6″), I find it difficult to find stuff that fits me and looks good. I was hoping you can provide some general style tips for shorter men.

A: See TheModestMan.com for a great site for shorter men style. But in our experience, as long as your clothing fits properly, there’s not much else to worry about.

Q: I recently picked up a Briefcase in a navy/ tan leather color way, would I match my wallet/watch/belt/etc. To the bag? What would you do in my situation?

A: Don’t think about it too much. Andrew is less of a stickler here, but I am more of a stickler. See video for details.

Men’s Summer Essentials Ebook

In this ebook, I’ll detail the items you need for summer, why you need them, and where to get them – in designer and budget-friendly options.

These items will work very well with the rest of your year-round essentials, so if you haven’t seen that series, check it out first.

My goal is to ensure you’re comfortable, wearing appropriate colors and items for the season, while looking amazing and not like a douchebag.

So download the book, pour a glass of… something (I prefer rosé) and let me show you the good stuff!






How Should A T-Shirt Fit?

Just like with polo shirts – if I had a dollar for every poor-fitting t-shirt I’ve seen a man wearing, I’d have two moneybins! So let’s make sure you look amazing in your t-shirts, as well.

When I first start working with clients, I always get pushback when I utter the next sentence, but they later admit I was right when they’re getting complimented all the time.

These rules apply to all men, no matter your age or body type. So trust me on these rules. I’m here to make you look amazing, not like some doofus who’s trying too hard.

Neck Opening

Crew necks are pretty standard, but just make sure it doesn’t fit too tight around your neck, or too loosely. If the collar looks stretched out or you can see some of your shoulder when wearing, that’s too loose.

If you’re wearing v-necks, you need to avoid deep v’s at all costs. Man cleavage is just… no. Some brands will have deeper v’s than others, so be wary of how deep it is. Just make sure the bottom point of the “v” doesn’t go past the top of your armpits and you’ll be fine.

Sleeves

Crew Neck T-Shirt Fit Guide Ashley Weston

The sleeves should hit around mid-bicep and lightly hug your arms. The sleeves shouldn’t be too tight where it looks like your biceps are being strangled. The image below has sleeves that are perfectly hitting the right place and hugging the arm to perfection.

You also don’t want there to be bunch of slack or room around the bicep, either. That just looks cheap and tacky and makes your arms look really small in the worst way possible. If the t-shirt fits well everywhere else, have your tailor slim the sleeves to fit your arms better. I have to do this with clients all the time.

Body/Torso

Armani Exchange Grey Pima V-Neck Tee

Like I say in all my shirting videos & articles, the perfect fitting t-shirt will be when you can pinch (not pull) between 1 to 2 inches of fabric on either side of your stomach, like the image above. This goes for EVERY SINGLE BODY TYPE. A lot of my larger clients fight me on this… until the compliments start rolling in. 🙂

Length

Crotch Measurements

The shirt should end somewhere between upper to mid crotch. I would rather it be closer to mid-crotch than upper-crotch because this avoids showing stomach when reaching up for things and allows it to be lightly tucked into the front of your belt/pants to break up your proportions – if you want.

The Best T-Shirts For Men

See my T-Shirt Essential Article for my favorite t-shirts that every man should own.