5 Shirts Every Man Should Own

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

Simple, timeless and will go with everything.  Every man should have a few crisp white dress shirts in his closet. Wear with everything from a suit to jeans.

2. Oxford

Another classic, make sure to get these in blue or white.  Oxfords are the ultimate casual staple for jeans or chinos and can be easily dressed up for business casual with a blazer.

3. Black T-shirt

I love the versatility of a black t-shirt.  It can be casual with jeans and sneakers or even dressed up with a blazer or suit.

4. Chambray shirt

This shirt has a cool, denim-like vibe and is perfect with chinos or as a more casual substitute for a dress shirt with a blazer and a tie.

5. Solid colored polos

Make sure you have a good rotation of solid-colored polos in basic colors like black, grey, navy, and white.

Bonus: Henley

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.

Shirt Picks

White Dress Shirts:

Burberry

Brooks Brothers Milano Non-Iron

The Tie Bar

Uniqlo

Zara

Oxfords:

Norse Projects Oxford

Brooks Brothers Milano Fit Oxford

Club Monaco Oxford

JCrew Oxford

Uniqlo Oxford

Chambray:

Brunello Cucinelli

Saturdays NYC

JCrew

Banana Republic

Amazon Goodthreads

T-Shirts:

James Perse

Rag & Bone

American Apparel

Uniqlo

H&M

Polos:

Brooks Brothers

Lacoste

James Perse

H&M

Uniqlo

Henley:

Rag & Bone Classic Henley

Rag & Bone Giles Henley

John Varvatos

James Perse

J. Crew

H&M

How To Wear Patterned Shirts

Whether you want to level up your business casual and weekend wardrobe or complement dressy looks, the right patterned shirt can do wonders. No matter if I’m dressing my clients formally or casually, I rely on patterned dress shirts to add both style and visual interest to whatever they’re wearing, and I’m going to show you how to do it so you look great – every time.

First, a quick word on formality.  While it’s not a hard and fast rule, in a basic sense, the bigger or bolder the pattern, the less formal the shirt is. For most of you dressing casually or in business casual, you’re home free, most patterns will definitely work. But, for some of you guys that work in more formal office environments or if you’re dressing up for a fancy wedding or evening event, keep in mind that the more subtle patterns will be much more appropriate. So now that we’ve got that established, let’s get some patterns in your life.

Stripes

Stripes can come in all manner of widths, from wide (sometimes known as Bengal stripes), to medium (pencil stripe), to thin (pinstripes) and since they tend to lean a bit more conservative, they’re also an easy place to start if you’re new to the game.

How Best To Wear Striped Shirts

As a general rule, the wider the stripe, the bolder the statement, and just like matching colors, the bolder the choice, the more simply you should approach the rest of your look. For casual and business casual looks, a simple pair of chinos or dark denim is a great option.  I also like stripes when worn with solid-colored or textured suiting and under a solid v-neck sweater with dress pants, denim, or chinos.

Checks

The world of checks is a wide one, but there’s no better way to add some instant personality to your shirt arsenal than with a few carefully chosen checked shirts.  There are many different options available, but, in my opinion, the three with the most versatility and style are windowpane, tattersall, and gingham. Both windowpane and tattersall feature types of graph patterns that can range in size and thickness and gingham goes one step further with a bolder, thicker check pattern that often combines a base color like white and one other color.

How Best To Wear Checked Shirts

As with stripes, the level of statement can vary, but my go-to rule remains, keep the rest of your look simple.  Dark-colored denim, chinos, and dress pants are the ticket, and if you’re going to dress them up, I recommend solid-colored suits and solid or subtle ties. On the tie front, I think geometrically patterned ties can look a bit too matchy-matchy with checked shirts, so be wary. Protip: for a less formal tie option, try a knit tie in a solid, complementing color. The texture and slightly less formal nature of a knit tie work really well with blazers, chinos, and denim for a dressy hybrid that’s great for business casual or a dressed-down Friday.

Geometric and Floral Prints

Now more popular than ever, print shirts are a great way to add a cool, modern edge to your casual looks and even suiting and dress clothes. Small-scale geometric prints are a great place to start if you want to keep it subtle but, I definitely recommend trying a bolder floral print too, it’s an easy, fun way to add a bit of stylish personality to your vibe.

How Best To Wear Geometric and Floral Prints

The printed shirt is all about letting the shirt do the talking, so I highly recommend denim or dark chinos in navy, tan or gray, especially if you’re going with a floral print, and finish with sneakers or loafers (I like driving mocs). Don’t be afraid to dress up a printed shirt too, pair it with a slim dark suit and some penny loafers or dressy leather sneakers for formal-but-not-stuffy settings like a cocktail party, fun summer wedding or night out. For a black belt-level move, try rocking the air tie (top button buttoned, no tie).

Plaids

When you’re talking plaid shirts, usually the pattern involves multiple colors and lines/boxes and the more things happening with the pattern (color, width, etc) the better suited the plaid will be to casual dressing. Be warned, though, it’s a slippery slope to full lumberjack hipster, so chop firewood at your own risk!

How Best To Wear Plaids

Ultimately these patterns are busy, and I recommend keeping plaids casual and subtle, so try them with denim, chinos, and shorts in solid colors, and finish them with shoes like sneakers or chukka boots. You can always “turn down the volume” of a plaid by layering it under a solid-colored sweater, lightweight jacket or pairing it with a dark-colored blazer in dressier situations.

Now that you’ve got some know-how and a few tips in your pocket, have confidence and make these patterns work for you! Your shirt rotation (and your wardrobe in general) are about to get an upgrade.

POTW: The Best Affordable Dress Shirts For Men

One of my favorite companies for ties, tie bars, and pocket squares – that I’ve been using way before I had this site – recently released a line of affordable dress shirts for men and I was… skeptical, to say the least. Well, I finally had the chance to test them out this past week and I’ve got to say – WOW! These really are the best affordable dress shirts for men that I’ve seen in a long, long time. Let me explain why in the video and below. Now I’m really excited for whenever they start expanding their offerings to include oxford button down dress shirts, too!

 

why I’m a fan

  • Two different fits are offered: Trim or Classic. Dorian tried the Trim fit (he has a lean build) which was the best fit I’ve ever seen in a budget-friendly brand. The sleeves and body of the shirt lightly hugged his body – it was as if the shirt was custom made for him. If you’re in larger man, whether from fat or muscle, then go with the Classic fit.
  • Two different collars: Semi-Spread and Point. I always recommend semi-spread for all body types.
  • The 100% cotton fabric is soft, but has just the right amount of thickness so it wasn’t see-through – which plagues a lot of cheap shirts (especially noticeable with white shirts!).
  • The price: $55. All I have to say is: This is a steal!
  • Sizing Tip: I did notice the sizing for the neck ran a little big, so go down 0.5″ of your regular neck size.

My favorites

$55 – The Tie Bar Pinpoint Solid Shirt in white
$55 – The Tie Bar Textured Solid Shirt in blue
$55 – The Tie Bar Chambray Shirt
$55 – The Tie Bar Multi Tone Gingham Shirt

2 Budget-Friendly Men’s Summer Essentials

Linen shirts and chino pants are 2 Men’s Summer Essentials that are also great if you live in a tropical, warm climate year-round. I more-than-briefly discussed them in my Summer Essentials Ebook, but since I’m about to leave on a tropical getaway (follow me on Instagram for all the fun), Dorian and I stopped by one of my favorite budget-friendly stores to show you what to get and why.

$20 – Uniqlo Premium Linen Shirt – white, light blue, light grey, and navy
$40 – Uniqlo Slim Fit Flat Front Chino Pants – navy, khaki, and white

Why I love them

  • Their linen shirts are super breathable, well-constructed, have a good, slim fit without being too slim, and they’re budget-friendly. What’s not to love? Be sure they fit according to these fit rules, though.
  • You can pair the shirts with chinos or shorts, either tucked or untucked and throw on some white sneakers, penny loafers, suede driving mocs with a casual belt and you’re good to go for casual or more dressy casual outfits.
  • The chinos have a fantastic slim fit (one of the best I’ve seen, actually) and I love that Uniqlo will hem them for free right after purchasing them in-store. There’s no other budget-friendly brand, that I know of, who does this. Be sure your chino pants are fitting properly before buying, though!

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

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!






Best Undershirts For Men

If you own any of the collared shirts I recommend in my Men’s Wardrobe Essentials Series, specifically the Oxford Button Down Shirt and a Semi Spread Collar dress shirt, you need to own some crew and v-neck undershirts. And before we get into it, there’s no scenario when you should ever wear a tank-top undershirt, AKA a wife beater – ever. You’ll see the lines underneath any shirt you’re wearing, and it just looks terrible. So let’s talk about the best undershirts for men and why you should own them. 

Undershirts are essential because

  • They provide a barrier between your sweaty, oily, deodorant-riddled skin and your dress shirts.
  • Due to this barrier, you may not have to get them cleaned as often, which will prolong their life.
  • They make dress shirts, specifically light-colored ones, look much better by not showing your skin and/or nipples through them.
  • They add another layer to your outfit for a little extra warmth or moisture wicking – depending on the weather.

How to Wear an Undershirt Under a Dress Shirt

You would think this is simple, right? Me too, but it’s very rare when a client knows how to wear an undershirt properly. A good undershirt is not something anyone should ever notice. If it’s noticeable, you’ve failed.

These are the 2 rules for wearing an undershirt:

  1. If you’re wearing a collared shirt without a tie, with the top button or two open, you need to wear a v-neck undershirt. Remember, no one should ever see your undershirt – even a bit of the collar.
  2. If you’re wearing a tie, you have to wear a crew neck undershirt. Otherwise, you’ll be able to see the v under the shirt and it looks like crap.

When should you go without an undershirt?

The only time I’d suggest not wearing an undershirt is if you’re wearing a white collared shirt. If you’re a lighter skinned guy, this is more geared toward you. Because most other undershirts might be seen through. But you can still try wearing a nude or gray undershirt to see if it’s not visible.

This problem isn’t as bad if you’re darker-skinned and wearing a similar-colored undershirt. That said, if you have darker nipples or nipples that tend to stick out a little bit, then an undershirt is required for you no matter what. Just make sure it matches your skin tone relatively closely.

Are Undershirts Supposed to be Tight?

A lot of my clients ask this question and the short answer is:
Sort of.

They shouldn’t be skin tight, but they should absolutely fit close to the body. Ideally, you want an undershirt to fit this way in the body and sleeves so you don’t see wrinkles or creases underneath your shirt. If the sleeves or body is loose, you’ll definitely see the line under the sleeves and wrinkles in the body – no matter the color of shirt you’re wearing over it.

Are Undershirts Supposed to be Thin?

Yes! They should be thin because they’re an underlayer and a thinner shirt will feel better and not add bulk to your frame. You don’t want this to happen regardless of your body type.

Should I have only white undershirts?

Not necessarily. I always have my clients wear undershirts that are closer to their skin tone. So if you’re darker skinned, you can go with a darker gray, brown, or black undershirt. Lighter skinned men should stick with light gray or white. A warning though, if you’re lighter skinned: a light gray undershirt under white or light-colored shirts is ok, but honestly, I’ve tried this a few times it and it tends to make the dress shirt look dingy or kind of faded. It’s not a good look, so I usually say to go without an undershirt in these instances.

Another quick note while we’re talking about white undershirts

I see this often with guys – if I can see exactly where your undershirt starts and ends around your neck or sleeves, (this only happens with light blue and white collared shirts), this means your shirt’s fabric is too thin and/or you need to change the color of your undershirt to match your skin tone better.

The Best White and colored Undershirts

These are the best undershirts that my clients and I love the most. Having tried all the major ones out there, these are my favorites:

Tommy John Second Skin Undershirts

Buy Tommy John’s Second Skin Crew and Deep V-Neck Undershirts

TommyJohnMensCrewNeckUndershirtsAshleyWeston12

Second Skin Crew and Deep V-Neck undershirts are my favorites. I like these a lot because they fit snugly on all body types and the fabric is super soft and has a little bit of stretch to it, so they won’t leave winkles showing through your shirts. But these niceties don’t come cheaply. Unlike their underwear, though, which I discussed here, they are very durable and will last you a good long while. They also make a nude and black colored undershirts to cover most men out there.

A quick note about their V-necks. Their images aren’t quite accurate and their titles are misleading.

Their “Deep V-Neck” is actually a regular v-neck length, so get that one and don’t waste your time with the regular v-neck, because the regular one is way too high and will absolutely be visible if you wear your collared shirts unbuttoned. I know the pictures look like the v is quite deep, but trust me, in person they’re not that deep.

RibbedTee Tri-Blend Undershirts

Buy RibbedTee’s Undershirts

 

RibbedTeeMensCrewVneckUndershirts Ashley Weston1

RibbedTee makes some of the softest, most comfortable undershirts I’ve tested. My clients said it was like wearing a soft fluffy layer of air. Their gray undershirts are great for lighter skinned guys, too, but they make many colors. You honestly can’t go wrong with any of their undershirts, but my clients were partial to the Tri Blend, Supima cotton and their Evo Tencell ones.

Calvin Klein Undershirts

Buy Calvin Klein Undershirts

CalvinKleinMensCrewandVNeckndershirts Ashley Weston12

For a budget-friendly option, I really like Calvin Klein’s Cotton Classic undershirts because the fit is great and the fabric is not too thick or thin, which is a problem with most other undershirts in this price range.

I like them because they also have different fits based on your body type – like slim and regular – which fit my larger or taller clients very well. They also make a similar undershirt to Tommy John called Body Modal, but I say just spend the few extra bucks and get the Tommy Johns instead because they’re just all around better.

Spanx Undershirts

Buy Spanx Cotton Compression Crew & V-Neck Undershirts

SpanxCrewVneckMensUndershirts Ashley Weston

I mentioned these in one of my AskAW videos because my clients who wear these LOVE them. If you’re looking to slim down your waist, belly or chest area, these are perfect. I like to say that they are like visual airbrushing tools. They’re not so snug that it feels like you can’t breath, which is important because I think a lot of men assume they’ll be too restrictive, but they’re just a little bit tighter than your average shirt, but they will literally drop you down a waist or shirt size in most cases.

Alright, that’s it. Those are the best undershirts for men – period!