Mens fashion dress shirt and jeans

How to Dress Up Denim tallNo one wants to give up his blue jeans.

But do you have to, if you want to move into the world of stylish dressing? No way, says modern fashion.

Style has embraced denim and then some. It’s the new millennium, baby! Jeans have shown up everywhere from the meatpacking plants to the red carpet.

If you’re looking to keep denim at the center of your wardrobe — a smart, sensible choice, given its durability and comfort — look no further than this short guide to walk you through updated looks that’ll keep your jeans looking sharp.

The Key Ingredient: High Quality Jeans

Here’s the key to looking good in jeans: get good-looking jeans. Makes sense, no?

There’s a limit to how far you can dress things up if you’re wearing a pair of battered old Wranglers. To really pull off a sharp look, you’re going to need jeans that are:

a dark color — deep indigo works best, or a deep blue-gray.

closely fitted — not “skinny jeans” tight, but without any sag in the crotch

straight-legged — boot cut can work, but it’s not as versatile

clean and neat — no obvious wear and tear from work on them

simple — no bells, whistles, straps, flap pockets, etc.

Don’t be afraid to spend a touch more than you’re used to spending on jeans to get the right pair. The difference between a pair of store-brand jeans and a  pair from a name brand can startle you, especially where the quality of the denim is concerned.

It’s worth spending a few extra bucks to get a good fit and a dark, dressy-looking dye. Cheap jeans will make whatever you wear them with look cheap as well.

The other key to all these looks? Skip the tennis shoes. No sneakers. Seriously. Maybe a pair of colored canvas sneakers, if you know what you’re doing and you want a little bit of a punk feel. But for the most part, these looks will look best with casual leather footwear — brogues, saddle shoes, suede of all kinds, chukka boots, Dr. Martens, you name it. Gym shoes are the kiss of death for a denim look.

Dressing Up Denim: Classic Looks

Don’t want to push too many fashion boundaries all at once?

Turns out the classic ways that men have been wearing jeans for decades can still work for you.

Most of these are “casual” styles. They aren’t meant for business. Wear them around town, or to low-formality settings like ballgames and taverns — but don’t be afraid to wear them in those settings. Done right, they’ll look better than some fancier outfits would.

Jeans and a T-Shirt

In a lot of fashion writing “jeans and a T-shirt” gets used as slang for “sloppy dressing.”

That’s something of a disservice. Marlon Brando and James Dean became heartthrobs and instant style icons when they appeared in Hollywood films wearing dark jeans and plain white T-shirts.

You can pull off that same classic look — if you’re smart about your shirts and your accents. You’ll need a plain-colored T-shirt (no graphics or logos) with a close fit, a sturdy-looking belt, and some leather work shoes or work boots.

As soon as you throw gym shoes or T-shirts with splashy graphics into the mix, you’re no longer classic. The look is ruined. Same goes for a baggy shirt — the T-shirt should be tight on your chest, and it fashion shouldn’t fall past your belt. But if you keep it close, plain, and paired with rugged accents, this look can be a great one.

Jeans and a Work Shirt

Upgrade slightly from a T-shirt and go with a long- or short-sleeved work shirt instead: something with a soft, turndown collar and a buttoning placket up the front.

This is a classic workwear look that does fine in social settings too. Just avoid the rookie mistakes: nothing in a blue that’s too close to the color of you jeans, and nothing with a company logo or (worse) one of those rectangular name patches with the cursive script on them.

The goal is to look rugged and a little rebellious, not like a grease monkey. Leave the shirt untucked for maximum devil-may-care effect.

Jeans and a Dress Shirt

To dress things up a notch while still remaining in the realm of timeless, working-class looks, pair quality blue jeans with a tucked-in dress shirt. Plain white, light gray, or light blue all work fine here, as do white shirts with light stripe or check patterns on them.

Make it look a little more relaxed by unbuttoning and rolling the cuffs. (Especially important with plain white shirts — dark pants and a long-sleeved white button down has a tendency to make you look like a door-to-door Mormon witness).

This look works best when you’ve got a nice belt, maybe with a big, decorative buckle on it, and some sturdy leather shoes or boots to go with it.

Dressing Up Denim: Fashionable Looks

Want to go a little beyond the classic and timeless style of wearing denim?

No problem — guys have been working blue jeans into more fashionable, sophisticated-looking outfits for a while now.


These are good looks for when you want to look a little dressier, and a little less blue-collar or working class. Whip them out for cocktails at fancy bars, evenings at trendy concerts or theater productions, and other “sophisticated” — but casual — settings.

Jeans and a Sweater

A fall/spring classic: dark jeans, light shirt, medium sweater.

There are a lot of ways to vary this one up. V-necks with collared dress shirts underneath look great. So do cardigans with T-shirts. You can wear the dress shirt tucked or untucked, sleeves showing past the sweater cuffs or hidden under them —  play with it to your heart’s content.

It’s beautiful in its simplicity. If you’ve got a good pair of jeans and a plain, solid-colored sweater, throw pretty much any sort of shirt on under the sweater and you’ve got an outfit.

Jeans and a “Busy” Sports Jacket

Most sports jackets have some sort of active visual element to them — either a textured weave, a colored pattern, or in some cases both (think a mottled herringbone tweed jacket, for example).

These “busy” jackets go well with the simplicity of jeans. Throw one on over a plain- colored dress shirt and a pair of dark jeans and you’ve got a nice visual mix that’s interesting but not overwhelming.

Get a good fit in the jacket to make it work well. A little softness and slouch is all right — this is a casual look — but you still want the shape of your torso to be defined.

Jeans and a Light Blazer

Solid-colored blazers are a little dicer with jeans, but you can still make them work.

The key here is to keep it pretty slim. Stay away from the boxy, squared-off “country club” flavor of blazer. If it’s got brass buttons on it, think twice about pairing it with jeans. Some will work and some won’t, but don’t take anything for granted.

Your other concern is colors — the traditional deep navy can be too close a match for some deep indigo jeans. You end up looking like you tried for a matched suit and failed. Make sure there’s a good, strong contrast between your jeans and your blazer that’ll be visible even at a distance.

Jeans and a Suit Jacket

Want to get a little funky? Take an old suit jacket (thrift stores are a great source for these) and throw it on over jeans and an eye-catching belt.

This is a look that’s built around deliberate contrast. You’re purposefully defying norms (a suit jacket should match its trousers, and you’re breaking that rule), so don’t go halfway here.

Wear a T-shirt under the suit jacket instead of a collared shirt, pair the outfit with some brightly-colored sneakers, add a colored vinyl belt instead of leather — some small touch that really jazzes it up makes this into a fashion look rather than an amateur mistake.

Exercise some caution here. Not all suit jackets are going to work with jeans. But if you find a color and a cut that works for you, go ahead and try the suit jacket/denim pairing — in the privacy of your own home. Double-check yourself in the mirror before you take it out for a spin.

Other Considerations

As we said above, footwear is key to a good denim look. Most jeans-based outfits look sloppy with gym shoes. Keep it leather, or go for funky colored canvas — nothing that looks like it’s actually seen a basketball or tennis court lately.

You should also put a little thought into your outerwear, if it’s cool enough to require any. Jean jackets are right out — that combination is called the “Canadian tuxedo,” and it’s not a compliment. There are a handful of men in the world who’ve pulled off a good jean jacket/blue jeans combo, and you’re probably not one of them.

Long, dressy overcoats are also a tough match. Stick to short, sturdy jackets that end around the waist or just below it. Blousons, field jackets, and leather jackets of all varieties work well here, as do corduroy jackets cut along the same lines as a classic jean jacket.

Finally, relax and have a little fun. Nothing makes jeans sexy like that slightly rebellious, come-what-may attitude, even when you’re dressing them up.

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