How To Roll Up Sleeves

This article is part of my Quick Tips series.

I’ll just cut right to the chase – there’s really only 2 good ways for how to roll up sleeves. Do one of these and never think about it ever again.

How NOT To Roll Up Sleeves Ashley WestonA quick note:

The images for how to roll up your sleeves below are from Esquire, whom I love and work with, but they’re rolling their shirt sleeves above the elbow. You should NEVER do this, because, while it looks great in pictures, it usually looks like the image to the left in person – lumpy and just, not good. It will never look as good as the pictures, I promise you.

 

The Basic Roll

How To Roll Up Sleeves - The Basic Roll - Ashley Weston

  1. Unbutton both buttons of the cuff. If there’s a button in the mid-forearm area, unbutton that one too.
  2. Flip the cuff over. Your cuff will dictate the width of your roll. If you have a stiff cuff, normally found on dress shirts, do not fold the cuff in half to make a slimmer roll. It will ruin that shirt’s cuff forever. If it’s not stiff, like with an Oxford button down dress shirt, then you can fold it in half for a less wide roll, although I wouldn’t advise doing a half roll. It usually looks better with the full cuff.
  3. Roll it again, and again, and one more time so that the top of the roll should stop just below the elbow, or mid to upper forearm (see the video for details).
  4. If you go above the elbow, the roll starts to get really bulky and it’s just not a good look. As a woman, I love when the shirt cuff hugs the muscular part of the forearm. It looks very… raaaaawwrrr!

The Italian Roll AKA The GQ Roll

How To Roll Up Sleeves - The Italian or GQ Roll - Ashley Weston

  1. Unbutton both buttons of the cuff. If there’s a button in the mid-forearm area, unbutton that one too.
  2. Fold the sleeve up, so the entire cuff is an inch or so above your elbow.
  3. Next, roll your sleeves up onto the cuff, using your thumb to sort of tuck in the shirt into the roll, but still allow a little bit of the cuff to be exposed at the top.
  4. The top of the roll should hit just below the elbow, by about half an inch. Then you hopefully have about an inch of shirt cuff exposed above the elbow.

The Oxford Button Down Dress Shirt

This article is part of my Men’s Wardrobe Essentials series.

One of the best collared shirts to own and what I recommend for all my clients, regardless of age or body type, is the Oxford Button Down Shirt. It’s versatile, comfortable and one of the more durable items you’ll have in your closet.

What is an Oxford Shirt?

Oxford Shirt vs. Dress Shirt – What’s the difference?

In my best Jerry Seinfeld voice: “So what’s with all these dress shirts?”

A dress shirt is any type of collared shirt with a stiff collar and long sleeves that may be worn with a suit or blazer. An Oxford Shirt is usually considered a type of dress shirt, but the Oxford shirt is different from a regular dress shirt in two ways:

  1. They usually have a button down-style collar which eliminates that problem of collars flopping around and/or laying flat and disappearing underneath a jacket’s collar.
  2. The Oxford Shirt is named after the specific weave of the fabric called, you guessed it, Oxford cloth. It has a basketweave structure and a lustrous aspect making it a popular fabric for a dress shirt.

While you can wear Oxford shirts with suits, I don’t dress my clients this way. The buttoned-down collar lends a more casual vibe to the shirt and takes attention away from the formality of a suit. Unless you’re going without a tie when wearing a suit, it’s just not my preference, but it’s acceptable. I normally pair them with a Gray Notch Lapel Suit (no tie), Blazer, Harrington Jacket, sweater, or by itself with the sleeves rolled up.

Why Should I Own Oxford Dress Shirts?

Well, because they’re awesome. But most importantly, because of these 3 points:

  1. Looks Good, Is Versatile
    They look great on every body type and they pairs easily with the rest of your essential wardrobe. They can also be worn in casual and professional settings and feel equally appropriate. Roll up the sleeves and leave it untucked over a pair of dark wash jeans and you’ve got a casual outfit. Button the cuffs, throw on a tie (or not) and wear under a suit or blazer and you’ve got a dress shirt. It’s one of the most versatile shirts in a man’s closet.
  2. Comfort
    The oxford material is typically woven in a basketweave pattern which allows it to be soft and comfortable and less prone to wrinkling than typical dress shirts made of silk or silk blends.
  3. Durability
    Due to the heavier fabric and weave the shirts are very resilient and durable, as opposed to non-weaved fabrics like silk or silk blends. I’ve got clients who’ve been wearing their Oxford shirts for over 5 years and they look good as new.

How should an Oxford Dress Shirt fit?

An Oxford Shirt should fit just like any other dress shirt you own.

The Best Oxford Button Down Shirts For Men

Since they’re all generally made of the same fabric and weave, the color is what matters most.

For my clients, I only recommend two colors to start because they look good on every skin tone, can be paired easily with the rest of your essential wardrobe and will cover any situation where a collared shirt is appropriate.

The colors are:

  • Light Blue
  • White

Designer Options

Brooks Brother Milano Fit Button-Down Collar Dress Shirt

Rag & Bone Thom Browne Oxford Shirt

Budget-Friendly Options

Club Monaco Classic Fit Oxford Shirt   

Uniqlo Mens Easy Care Long Sleeve Shirt

3 Ways to Wear Oxford Button Down Dress Shirts

Brooks Brothers Milano Fit Button-Down Collar Dress Shirt

Levi’s 511 Slim Fit Stretch Jeans 

Daniel Wellington Classic Sheffield 36mm

Allen Edmonds Newland Ave Casual Belt

Converse Jack Purcell Signature Leather

Brooks Brothers Red Fleece Merino Wool V-Neck Sweater

Brooks Brothers Milano Fit Button-Down Collar Dress Shirt

Brooks Brothers Milano Fit Plain Front Trousers

Daniel Wellington Classic Sheffield 36mm

Allen Edmonds Poplar Dress Belt

Allen Edmonds Carlyle Plain-toe Oxfords

Brooks Brothers Red Fleece Micro Check Suit Jacket

Brooks Brothers Milano Fit Button-Down Collar Dress Shirt 

Levi’s 511 Slim Fit Stretch Jeans

The Tie Bar Solid Pocket Square with Black Border 

Allen Edmonds Poplar Dress Belt 

Allen Edmonds Carlyle Plain-toe Oxfords

Outfit Inspiration

The Semi-Spread Collar Dress Shirt

The Semi-Spread Collar Dress Shirt is *the* holy grail of dress shirts. When I was conceiving the idea of this series, this was the article of clothing that started it all because it embodies everything an Essential means to me:
  • It works for everybody – regardless of age, face shape or body type.
  • It works in all scenarios.
  • It will never go out of style.

A semi-spread dress shirt will look great dressed up or down, with or without a tie, with the sleeves rolled up, underneath a v-neck sweater or even a leather jacket.

In all your outfits, but especially when dressing up, you want to put your best foot forward, and a pillar of a sharp outfit is the dress shirt.

If you’re new to dressing, looking and feeling better, it’s extremely easy to get bogged down by the minutia. So let me save you the time and just say don’t worry about other collars until later on in your style journey.

What is a Semi-Spread Collar?

Let me show you via the simple image below. There are other types of collars such as the club, mandarin, tab and contrast collar, but those have extremely specific use cases and won’t work for most people, so let’s stick to the most common ones below:

DressShirtCollarTypes

Why A Semi-Spread and Not..?

The collar is very important. It makes or breaks an outfit. The collar of a shirt borders your face, so this is the first thing people see when looking at you since our natural tendency is to look at the face/head and move down.

Also, the type of collar informs the viewer, often unconsciously, what the rest of your outfit should be and how to perceive you.

Point vs Semi-Spread

A point collar, the most common one you’ll see in stores, simply doesn’t look good on most guys because it doesn’t fit most faces or body types. I rarely dress my clients in them because it’s just not worth the hassle when there’s something that looks good on all men. Whenever I see someone wearing a point collar, they almost always shouldn’t be wearing it because it’s not for them. I’ll do a more detailed post about this later, because I can go on forever about my dislike of the point collar.

Full Spread vs Semi-Spread

The full spread collar is similar to the point collar in that it is acceptable in only specific contexts and body shapes. These have gotten more popular over the last few years and I’d choose them over a point collar, if given the choice.

They’re great if you’re wider or broad shouldered, but I see a lot of guys wearing them who really shouldn’t be. These are also the same guys who have a full windsor knot to fill in the space of a spread collar, and on thinner guys, this is style suicide! Don’t do it!

What Colors Should I Get?

You’ll want to stick with white and light blue because like the gray suit, it’s a blank canvas that goes with anything you pair it with and you can easily add your personality via accessories (ties, pocket square, etc). Later on, you can play with the color and pattern, but for right now, these two colors are timeless, sharp, and don’t require any thinking when you put an outfit together.

How Should a Semi-Spread Collar Dress Shirt Fit?

I’m glad you asked. Head over to my Fit Guide for details about how all your dress shirts should fit.

The Best Semi-Spread Collar Dress Shirts

Budget Friendly

J Crew Ludlow Semi Spread-Collar Shirt
Zara Semi Spread Collar Shirt 

For the price and quality, I love J.Crew’s and Zara’s semi spread collar dress shirts. The collars are just the right spread and height, and the fit is nice and tailored. It’s a staple shirt that they always have year after year that I can always count on.

Designer

Burberry London Slim Fit Stretch Cotton Blend Shirt
Brooks Brothers Milano Fit Shirt 

My, hands down, favorite dress shirts come from these designers. The quality and fit is spot on. Burberry London and Emporio Armani’s collar height is perfect for most men, while Brooks Brothers’s tends to be a tiny bit taller so if you’re slim and under 5’7′, then I’d advise to go with the former brands. Side note, the Brooks Brothers dress shirt says it’s a spread collar, but it definitely fits like a semi-spread.

3 Ways To Wear

Ashley-Weston-Semi-Spread-Collar-Dress-Shirt-Look-1-Full Ashley-Weston-Semi-Spread-Collar-Dress-Shirt-Look-1-Detail

True Vintage Revival TVR504Burberry Lightweight Lambskin Bomber Jacket 
Brooks Brothers White Milano Fit Spread Dress Shirt
Brooks Brothers Milano Fit Plain Front Flannel Trousers
The Tie Bar Knitted Tie
The Tie Bar Brushed Straight Silver Tie Bar
Brooks Brothers Calfskin Belt
Allen Edmonds Carlyle Dress Shoe
True Vintage Revival Glasses

*NOTE: You choose the type of lenses (shaded, etc.) during checkout for the sunglasses above.

Ashley-Weston-Semi-Spread-Collar-Dress-Shirt-Look-2-Full

Ashley-Weston-Semi-Spread-Collar-Dress-Shirt-Look-2-Detail

Brooks Brothers Red Fleece Grey Suit Jacket 
Brooks Brothers Red Fleece Grey Suit Trousers
Brooks Brothers White Milano Fit Spread Dress Shirt
The Tie Bar Grenafaux Midnight Navy Tie
The Tie Bar Solid Pocket Square with Navy Border
IWC Portugieser Automatic Watch
Allen Edmonds Carlyle Dress Shoe

Ashley-Weston-Semi-Spread-Collar-Dress-Shirt-Look-3-Full

Ashley-Weston-Semi-Spread-Collar-Dress-Shirt-Look-3-Detail

Burberry Prince of Wales Virgin Wool Suit Jacket 
Brooks Brothers White Milano Fit Spread Dress Shirt
J Brand Tyler Taper Fit in Rasalas
The Tie Bar Solid Pocket Square with Burgundy Border
IWC Portugieser Automatic Watch
Brooks Brothers Calfskin Belt
Allen Edmonds Carlyle Dress Shoe

Outfit Inspiration

 

Model: Michael Tribby

Barbour Jacket & Gingham Shirt

Take note of the functional, well-designed Barbour Jacket.  With more pockets than you’d ever need, the Barbour jacket is practical, and like a leather jacket, will look age nicely.  Pair with a blue gingham shirt and navy trousers to complete this outfit.  For added warmth, throw on a navy sweater.

 

Designer Option:

 

Vince Utility Suede Trucker Jacket, $895
Ermenegildo Zegna Gingham Dress Shirt, $450
ATM Anthony Thomas Melillo Modal Jersey Tank, $70
John Smedley Bryn Fine-Knit Merino Wool Cardigan, $320
Rag & Bone Fit 2 Chino, $295
Tom Ford Andrew Sunglasses, $455

 

Budget-Friendly Option:

 

ASOS Slim Fit Jacket In Khaki With Utility Pocket Detail, $44
Zara Gingham Check Shirt, $30
Alternative Apparel Basic Tank Top, $24
Uniqlo Extra Fine Merino V-Neck Cardigan, $50
J.Crew Broken-In Chino in 484 Fit, $75
Warby Parker Black Thatcher Sunglasses, $95

 

Photo Credit: Tommy Ton