Do you ever find yourself stuck wondering if this goes with that?

Have you ever asked yourself:

• “Does this shirt go with that pair of pants?”
• “Can I wear these jeans with that shirt and tie?”
• “Is it OK to wear a parka with a suit when it’s cold out?”

The missing piece in all this is understanding how casual or formal something is, and then successfully wearing it with other clothes that are similarly casual or formal.

When you’re in a tuxedo, it’s obvious you’re dressing formally. If you’re in sweats and a T-shirt, clearly, that’s a casual outfit.

What about everything in the middle?

You have a lot of outfit options between “sweats and a T-shirt” and “tuxedo”, but it’s not always easy putting outfits together, and knowing exactly if this goes with that.

This is where the Spectrum of Style Formality comes into play!

How to use the Spectrum of Style Formality

Within every category—shirts, pants, shoes, outerwear—clothes are listed in order of formality, from least to most formal.

Clothes on either end of the spectrum are more obvious—a T-shirt is clearly casual, a tuxedo shirt is clearly formal—it just gets confusing somewhere in the middle.

Now that you have these as a reference, you’ll never wonder how casual or formal something is.

Quick tip: If they’re relatively close in level of formality, they probably go together.

Let’s break it down…

Spectrum of Style Formality: Shirts

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T-Shirt (also V-neck shirts)

Everlane, $18

Tees (and V-necks) are the base of any man’s wardrobe. They’re also the most casual shirt you can wear.

Henley

Gap, $40

The henley is a more interesting alternative to your basic T-shirt, and can be worn as a layering piece, as well as on its own.

They come in long and short sleeve versions, and many of them are made from a waffle weave fabric.

Polo shirt

J. Crew, $55

The polo shirt is my preferred casual shirt. Just make sure you get one that fits well in the body and has sleeves that hit above the bicep (read: aren’t too long, don’t flare out).

Sport shirt / chambray work shirt / OCBD

Sport Shirt, $69 | Chambray, $88 | OCBD, $69 – all J.Crew

Sport shirts—everything from your favorite casual gingham or plaid shirt to your workhorse chambray and Oxford cloth button-down—are arguably the most versatile out of the bunch, able to be worn with everything from shorts and sneakers, to suits and sport coats (that whole high/low look).

I put the OCBD on the spectrum as slightly more formal, because it’s a traditionally preppy (and common American office) style and can be worn with khakis, a tie, navy sport coat, and brown loafers.

Dress shirt

BOSS, $125

Dress shirts come in a variety of patterns and textures, and most are made from fine gauge fabric, have stiff cuffs and collars, and are usually longer in the body so they stay tucked in.

(You should always tuck in your dress shirts.)

Tuxedo shirt

Hackett, $210

Only for the most formal of events, the traditional tuxedo shirt has a pleated front, option to use studs, conservative spread collar (not cutaway) and french cuffs.

If you’re attending a white tie event—the most formal of formal events—go with a pique bib and wingtip collar. The tuxedo shirt shown in the spectrum is an example of a pique bib.

Spectrum of Style Formality: Pants

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Shorts

J. Crew, $69

Perfect for warm days, tropical climates, summer season, hanging out by a body of water, etc.

Joggers

Uniqlo, $20

Joggers are usually made from twill or fleece and have elastic at the cuffs and waistband. While the twill version steps up the formality a bit, the silhouette (think sweatpants) is still inherently casual.

Denim

Levi’s, $128

There’s a range of formality with jeans. The lighter and / or more distressed your pair is, the less formal it is. The darker-wash, raw, non-distressed versions are considered more formal.

Chinos

Uniqlo, $40

There’s a range of formality within chinos as well. If your chinos resemble 5-pocket denim, they’re more casual. If they’re modeled after dress trousers both in silhouette and fit, they’re more formal.

Dress trousers

Brooks Brothers, $198

The most formal option of the bunch. Typically made from (though not restricted to) wool, with dressier details like side seam pockets, welt back pockets, tab closure, suspender buttons, and cuffs.

Spectrum of Style Formality: Casual Shoes

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Flip flops (also sandals, or anything that shows your toes)

Havaianas, via Amazon $20

Flip flops are perfectly fine for hanging out, or when heading to, the pool or beach. Also great for when you’re at the sauna, steam room, or shower at your gym. They don’t belong in any other situation, really.

Sneakers

Greats, $159

Your most casual shoe option. I always recommend a minimalist white sneaker in canvas or leather. Leather elevates your look a bit more (meaning you can dress up white leather sneakers), and they’re also easier to keep clean.

Boat shoe

Sperry, via Amazon, $ varies

Boat shoes aren’t just for preppy New Englanders on yachts these days. Grab a pair in standard tan leather and wear them with denim or chinos for a look that’s a step above sneakers on the formality scale.

Chukka / Driver

Clarks chukkas, via Amazon | Cole Haan drivers, via Amazon ($ varies)

A chukka is the perfect transitional weather boot, as well as celebrity chef Anthony Bourdain’s preferred footwear of choice when traveling. It also happens to be comfortable as hell and extremely versatile, working with plenty of different outfits.

The Clarks desert boot—desert boots are a type of chukka—comes with a crepe sole, but other brands make sleeker versions with slim soles that are easier to dress up with trousers and a sport coat.

The driver (or driving moc) is another worthy alternative for your casual shoe collection. These work well in warm weather, my preferred model being made from suede, with a minimal rubber sole.

Casual boots

Thursday Boots, $199

A rugged casual leather boot sits one step above your desert boots and drivers, as far as formality is concerned, yet still very much on the casual end of boot styles.

We’ll get into other, more formal, boot options in the next section.

Spectrum of Style Formality: Formal Shoes

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Dress boots

Allen Edmonds via Zappos, $445

Dress boots, such as sleek Chelseas (with slim leather soles), Jodhpurs, and other styles are great alternatives to dress shoes, though I wouldn’t replace all my dress shoes with boots.

While Chelseas and Jodhpurs have distinct looks, most laced dress boots can look like regular brogues or cap toes, and people won’t notice it’s a boot unless your pant leg is lifted.

Because dress boots come in many different styles, it’s difficult pinpointing exactly where they lie on the formality spectrum.

Dress loafers

Allen Edmonds via Zappos, $395

Loafers are the most casual of dress shoes. There are different versions, from the traditional American beefroll penny loafer, to the moc toe loafer with a longer toe and a sleeker silhouette.

Brogues / Wing tips / Cap toes

Wing tips, $395 | Cap toes, $395 (both Allen Edmonds via Zappos)

There are a wide variety of brogues, from wing tips (brogues with the decorative perforations on an extended toe cap and often throughout the uppers) to more simple cap toes (with broguing only along the edge of the toe cap).

In general, the more broguing, the less formal the shoe is.

Plain toe oxford

Allen Edmonds via Zappos, $395

The plain toe oxford is a very clean, classic option for business wear, a notch above cap toes in formality. Remember, the fewer decorative flourishes on a shoe, the more formal it is.

Wholecut oxford

Kingsman via Mr. Porter, $950

Wholecut oxfords have no cap over the toe box, but it may or may not have minimal decorative broguing at the toe. It is cut from one whole piece of leather.

Patent leather loafers, oxfords, or opera pumps

Tom Ford via Mr. Porter, $1390

These shoes are reserved only for the most formal black and white tie events.

Spectrum of Style Formality: Outerwear

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Technical outerwear (activity-specific)

Nike, $100

Any jackets that are specifically made for certain activities (running, skiing) and / or constructed from a water- and weather-resistant material (windbreakers, rain coat, down coat) would be the most casual outerwear option.

Vest

Uniqlo, $30

Perfect for layering, a vest’s formality can vary. Anything obviously designed for performance, water-, or weather-resistance would be more casual. Quilted vests made from twill or wool in somber colors can be considered more formal (though still, by all means, casual).

Field jacket / Denim jacket

Alpha Industries, via Amazon, $140 | Levi’s, via Amazon, $70

Field jackets (like those modeled after the military-spec M-65) and denim jackets are inherently more casual, though there are ways to combine it with more formal items for that perfect high/low look.

Quilted jacket / Bomber jacket

Barbour + J.Crew, $179 | Schott G-1, $725

Quilted jackets, though often made from nylon, can work well with outfits ranging from casual to business casual and provide the warmth and weather protection you may need.

Classic bombers are shorter and hit at the hips, have ribbed cuffs and a ribbed hem, and a front zip closure. Some models have collars, while others don’t. You can find the bomber style made in a variety of materials, from leather and wool to nylon and fleece.

Natural materials in somber colors (leather, wool) would skew more formal, while man-made materials and brighter colors skew more casual.

Pea coat

J.Crew, $298

Pea coats are the most versatile option for a smart or business casual look. They’re warm (especially when lined with an insulating layer) and easily worn with trousers as they are with jeans.

Some pea coats are made a bit longer, which is perfect if you want to wear a suit jacket or sport coat underneath, but in most cases, an overcoat would work better, simply because most pea coats are too short and you would see the suit jacket peeking out at the bottom hem.

Trench coat / Duffle coat

Burberry via Mr. Porter, $1795 | Gloverall via Bloomingdale’s, $645

The trench coat is a dressier alternative to sporty, nylon rain jackets.

They’re traditionally double-breasted and made from 100% khaki gabardine and are longer (to the knee). Trenches also have a few military-inspired details such as epaulettes and a gun flap, as well as features to keep you dry in inclement weather, like sleeve straps, a deep yoke, and storm pockets.

While the Burberry trench is iconic (with a price tag to match), you can find a great model from London Fog. Another option would be to snipe a used Burberrys trench coat from eBay.

According to my buddy, Raphael, over at Gentleman’s Gazette, the older Burberrys trenches are better anyway (pre-1999) and were made almost entirely in England.

Just like the trench, there may be many variations of a duffle coat today. The traditional models are longer in the body (anywhere from mid-thigh to knee length), with two distinctive details: 3-4 toggle closures and a hood.

Overcoat / Topcoat

Suitsupply, $639

Overcoats—nowadays used interchangeably with the term, topcoats—are coats specifically worn over suits and sport coats. These can range from knee to ankle length.

Stylistically, they can be single or double breasted, made from heavyweight wool or cashmere in somber-colored wools like grey, black, and navy, to more interesting colors and patterns.

They come with either flap or patch pockets, and notch or peak lapels. Notch lapels are considered less casual than peak lapels, though overall, the coat is appropriate to wear with formalwear.

“Now that I know how formal or casual something is, how do I use it to put together outfits?”

The two ends of the spectrum are a bit more obvious.

• If you’re wearing a casual shirt and pants, then keep all the other elements of your outfit casual as well.
• If you have to wear a tuxedo, keep all the other elements of your outfit formal.

Where it can get tricky is everything in the middle, where clothes range from the dressier side of casual, to the more laid-back side of formal.

Here’s a secret, though: As long as you stick with stuff in the middle of the spectrum, you can’t really go wrong.

Let’s look at an example

1. Start with a pair of dark denim, right in the middle of the spectrum.
2. Next, a shirt. Let’s go with a polo shirt.
3. For shoes, a pair of chukkas.
4. And finally, a light jacket. Let’s go with the field jacket.

Levi’s, $128 | J.Crew, $55 | Clarks via Amazon, $70 | Alpha Industries via Amazon, $140

See how easy that was? You’re basically picking and choosing anything within that middle section of the spectrum.

And don’t forget, you have to imagine the shoe spectrums as one continuous image, from casual to formal.

The chukkas, while farther right on the casual shoe spectrum, is still in the middle of the shoe spectrum as a whole (once you stick the two together).

Here’s another example

1. Starting with pants, let’s go with chinos this time.
2. For the shirt, an OCBD.
3. And shoes, we’ll go with work boots.
4. For the outerwear, a pea coat (assuming it’s cold out). If it’s not that cold, then a denim or a field jacket.

Uniqlo, $39 | J.Crew, $69 | Thursday Boots, $199 | J.Crew, $298

The lesson here: For the majority of your everyday outfits, just pick and choose from the middle of the formality spectrum.

“Can I mix the super casual stuff with the clothes in the middle of the spectrum?”

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Sure. You can throw shorts into the mix if it’s warm out. Or maybe you want to wear a layering vest with denim and a sport shirt, or a windbreaker with chinos. Go for it!

On the formal end, I would certainly stick to tradition as closely as possible—I’m talking about black tie and white tie—but even with suits, you have a bit of leeway, especially in a business casual environment.

What other questions do you have?

Now that you know everything in the middle of the formality spectrum is fair game, you should have an easier time putting together outfits, because you know those clothes go well with everything else in the same range.

You can also throw more casual pieces into the mix, and still be in the clear.

Just make sure to respect the tradition of formal wear, should you ever find yourself in the position of going to a black or white tie event.

If you have a combo you’re unsure goes well together, let me know in the comments, and I’ll help you out!