How to Style Jeans – Casual vs. Dressy

How to Style Jeans – Casual vs. Dressy

I love jeans, and I’d wear them every day if I could. Your jeans style can take you from super casual to dressed up for a night on the town. It’s all in how you create your look with complementary pieces of clothing and accessories. It’s easy and it’s fun!

Here are some things to keep in mind if you want to build your jeans style to be versatile and classy.

Think of every jeans purchase as an investment.

This might sound strange and you might need a minute to wrap your head around this idea. But there really is a difference between $100+ jeans and jeans that are priced below $100. I would rather have one pair of premium jeans than 4 inexpensive pairs. The quality of the denim is the first noticeable difference. The fabric in more expensive jeans has the ability to stretch for comfort but also to hold its shape and not stretch out. The quality of the construction is better. Premium priced jeans also last longer (especially if you launder them gently – see below for that).

Note: Most of my premium jeans have been purchased on sale. Find a brand that makes you look amazing, and keep your eye out for sales. Sign up for your favorite denim brand’s email newsletter, and you’ll be the first to know when there’s a friends and family sale. It’s hardly ever necessary to pay full price!

Build a jeans wardrobe the includes a variety of styles.

Variety is the spice of life, right? Let’s extend that to our jeans style. Your denim collection should include different styles – you want to have styles that go with your moods, with the occasion you’re dressing for, styles that work for when you’re feeling less svelte . . . You get the picture. The tried-and-true 5-pocket style is probably what we think of when talking about jeans. And, YES, we all need at least a pair or two. And how about straight leg, cigarette leg, flares, skinnies, bootcut, trouser style, crop, distressed. Then there’s color! Jeans come in every color. You want to have a pair of white and a pair of black to start. Then be sure to add at least one fun color – choose a color that you love and that makes you feel great when you wear it.

My first pair of colored jeans was a pair of bright blue AG Jeans. I loved them and wore them so much that their perky days are behind them, and they are now relegated to errand running attire. My colored jeans wardrobe has grown and now includes: pink, sage green, olive green, black, white, off white, and gray. On my wish list is red and purple.

Treat your jeans with TLC!

So you’ve made an investment in jeans you LOVE. Now you want to make them last and look great every time you wear them. Here are a few do’s and don’ts”

  • Always wash you jeans in cold water, gentle cycle, inside out.
  • Never dry your jeans in the dryer – it’s the fastest way to age them. Here’s my formula for drying: Keeping wet jeans inside out, toss them in the dryer on a low heat setting for 10 minutes. This will relax any wrinkles or creases and will prevent them from drying stiff. Remove them from the dryer after 10 minutes, turn them right side out, and hang them to dry on a pants/skirt hanger.
  • If there is ever any mending needed, do it right away to preserve the quality. If you have distressed jeans, you may want to apply an iron-on patch behind the tears or abrasians for longer life.
  • Store your jeans neatly when you aren’t wearing them by hanging or folding them.
  • Here’s a trick I’ve used for front pockets that just won’t stay tucked in or when pockets show through the fabric of white jeans: Sew the pocket closed and then trim the pocket as close as possible to the seam you’ve created. This can also be done by a seamstress if you’re not comfortable hacking away at your new premium jeans.

You’re ready to create great jeans style!

When you want to keep it casual, remember to have fun with it. Casual doesn’t mean sloppy or boring. Pair your jeans with a cute top and fun, casual shoes or sandals. Don’t leave out the accessories! Even when I’m running to Target, I feel slightly undressed if I’m not wearing earrings.

For more dressy occasions, your jeans can hold their own when styled with dressier fabrics, maybe a tuxedo-inspired top or jacket. Add a great pair of heels, a fun purse, and special occasion jewelry, and you’re set.

Remember to dress to impress . . . YOU! Don’t focus on what anyone else will think of what you are wearing. You can be the style setter.

And photos

The photos below feature 8 different jeans styled two ways: as a casual look as well as a “going out” look. Some of the looks here may give you ideas you hadn’t thought about. Go shopping in your closet! I’ve included the brand of jeans below each photo for reference in case you want to check it out.

*Thanks to my husband John for playing the role of photographer with my  new Sony A6000 camera I just purchased from my son!

Distressed Jeans Casual

YOGA JEANS DISTRESSED – This is one of my favorite pairs of jeans (they aren’t to wear for yoga!). I have to admit, I did pay full price for them, which I think was around $200 (yikes!). But they are amazing, totally worth it, and I haven’t had one minute of buyer’s remorse. I rationalized buying them because I had purchased a gift certificate at an fundraiser auction for the boutique that was selling them – I had to spend it on something! They are kind of fun with a bit of distressing that you can see in this casual look shot. I did add a light blue iron-on patch behind the largest abrasian on the front so it wouldn’t fray more. I really like that the rise on these jeans is a little higher than some. I styled these with a denim on denim look and my fun $24 Gap perforated pink slip-ons. I added my favorite Stella & Dot mixed metal Sutton necklace that has an industrial feel.

Distressed Jeans Dressy

Here are the Yoga Jeans styled as a dressier look – not super dressy, but something that’s perfect for a lunch date or even dinner out. The top is one of my Stitch Fix scores from my Fix #1! I love that it’s lightweight and flowy and can be tucked in or worn out. The shoes are a fun pair of Borns that I purchased a few years ago and the purse is an inexpensive trendy style from Charming Charlie (check out one of the stores if you haven’t yet – great, inexpensive accessories!).

Skinny Jeans Casual

AG SKINNY JEANS – These skinny jeans have so much stretch that they fit almost like leggings, but they aren’t! I love the dark blue color and since the fit is so nice, I can wear them with long and short tops. I bought these on sale a few years ago at Anthropologie. I love Anthropologie, but the prices are pretty high. If you shop there, be sure to check out the sale rack, usually located in the back of the store. I’ve found several pairs of AG Jeans on different occasions at great sale prices. Here I’ve styled the jeans with a long white shirt (Chico’s No Iron Lia Shirt – love it!), and I’m wearing my Banana Republic Dalmation print flats (animal print is a staple in my closet) and the same Stella & Dot Sutton necklace.

Skinny Jeans Dressy

This look with the AG skinny jeans is not super dressy, but nice enough that it could be appropriate in some work environments. I’m wearing another of my Stitch Fix tops (came with my Fix #2) and my favorite Vince Camuto peep toe booties (the ones I couldn’t stop thinking about until I bought them). The heels are really high (almost 4″) – way higher than anything else I have. Despite that, they are pretty comfortable and I’ve been wearing them a lot and really enjoying the slimming effect of higher heels!

Boot Cut Jeans Casual 2

MOTHER DENIM BOOTCUT JEANS – I discovered Mother Denim on a long weekend getaway to Seattle at Anthropologie. These were another full-price purchase. But they were so soft and comfortable and long legged! I’ve styled this bootcut with a casual and bright summer top (from Ann Taylor a couple of years ago) and my Vince Camuto peep toes. Bootcut jeans really look great with a higher heel and it’s a super slimming look. It’s probably the most flattering jeans style that works for just about everyone. I wish the necklace in this shot was easier to see. It’s one of my favorite pieces from the Liquid Metal Jewlery line: Lioness Necklace. The great bag (I love stripes!) is the Fillmore Tote from Stella & Dot.

Boot Cut Jeans Dressy

I love this look with the dark wash Mother Denim bootcut jeans paired with a sleek black top (another top I love from my Stitch Fix #1 shipment). The top has a bold gold zipper on the back, which gives it a polished and shiny look. Dark denim automatically has a dressed up feel. The heels are a strappy and HIGH heel cage style from Banana Republic (bought several years ago for some special occasion). I love the shoes, but with the narrow and high heel, they are best suited for dinner in a restaurant when I’m mostly sitting – but what’s the point when they are under the table most of the time? The chunky gold link necklace is also Banana Republic (received as a gift). This is a classy and svelte look for an evening out.

Flare Jeans Casual 2

DAVID KAHN FLARE JEANS – David Kahn jeans were my very first pair of premium jeans (a different pair, not these). I’m not sure this brand is still available – when I was looking up their website to link here, most of the search results were for retailers like eBay or Poshmark that sell used clothing. I think I purchased these flare jeans about 8 or 9 years ago. The flare style isn’t my favorite – flares are a little wider than bootcut. This particular pair is too short to wear with a higher heel, which would probably be flattering. I styled this as a VERY casual look with a simple striped tee from Target and a pair of white flat slide sandals. I don’t love the belt with this outfit – I think it would have looked better with a wider belt.

Flare Jeans Dressy 2

In this photo the David Kahn flares are styled with a fun top from Gap that has a boho feel style-wise but a contemporary stripe print. I’m wearing one of my three pairs of Eric Michael Cody wedge sandals (yes, they are really that awesomely comfortable). The iconic Speedy LV bag was a 30th birthday gift from my husband (then fiance). I’m making it last as replacing it is not in my budget! The jeans style here is a more casual dressed up look with the faded jeans. The accessories, especially the designer bag, elevate it.

Trouser Jeans Casual

BLACK HOUSE WHITE MARKET TROUSER JEANS – These are a fun trouser style that to me has a bit of a dressy look no matter what is paired with them. The length is long, which is appropriate for trouser styles, so even with a casual vibe, a chunky heel, wedge, or platform is best. I bought these several years ago for a night out to dinner and a live show, and I don’t think WHBM has anything like this now. Their jeans hover around the $80-$90 price range. If you like this look, search for trouser style jeans. I’ve paired the jeans with a navy and white stripey t-shirt from Uniqlo (bought on sale for $5.90!) and a pair of muti-color (black and tan) wedge sandals from Target. The necklace is probably the one that attracts more attention than any other piece of jewelry I wear! It’s a tiny vintage-look flask (it really opens). I purchased it from Jewelmint, a subscription fashion jewelry site that doesn’t appear to be operating any longer. It’s my go-to necklace  – easy to wear and goes with everything.

Trouser Jeans Dressy

This outfit looks like it can take me to dinner, a show, or even to the office. I’ve paired the trouser jeans with a sheer black with white polka dots blouse and my Banana Republic high heels. The red purse is Anne Klein – I’m pretty sure I’ve had it since the 1990s! I love the pop of red. Don’t forget to bring some fun accessories into play when you are styling your jeans outfits. The necklace I’m wearing is beautiful, super cool, and sparkly: the Swarovski Stardust Deluxe Bracelet (can be worn as a choker to, like I am here. (It’s on sale right now for $49.50.) This look is classy and sophisticated.

Gray Jeans Casual

BANANA REPUBLIC GRAY SKINNY JEANS – I love jeans in different colors. Somehow we think of blue denim as dressed down, and when we wear jeans in a different color, they seem a little more . . . well, just more. I’ve paired these gray skinnies with a Gap pink linen boyfriend shirt – it’s oversized and kind of cool.  (Similar boyfriend shirt in the link – I sized down.) I’m wearing my favorite Bucketfeet slip-on canvas shoes (artist designed – check out their website). The bag was another Stitch Fix win from Fix #2 – it’s been my almost everyday bag since I got it.

Gray Jeans Dressy 2

Here are the gray BR skinnies with an dressier feel. The long polka dot, chiffony sleeveless top and the strappy , block heel sandals (I’ve hung on to these since the 90s!), make a comfortable look but can take this outfit to a baby shower or girls lunch date. The small purse is also a cool throwback – from the 80s (gifted to me from a friend who was closet editing).

White Jeans Casual

AG WHITE CIGARETTE LEG JEANS – White jeans should definitely be a foundational piece in everyone’s wardrobe. These were a great purchase on sale at Macy’s a few years ago. I love these jeans – they are soft and comfortable and keep their shape. I like the cigarette leg – just between skinny and straight. I’ve styled these white jeans with a casual black and white striped tank (J. Crew) and some super fun Melissa sandals (they’re plastic!). The purse is canvas – not sure where I bought it several years ago (maybe Target). Love the pairing of black and white – so classic.

White Jeans Dressy

In this dressier version, I’ve styled the AG white jeans with a black and white striped tank and sheer jacket ensemble. It still has that classic black and white look but with the black pumps, fabric of the top and jacket, and sparkly necklace (part of the Stella & Dot Sutton necklace), I’m ready for a night out.

Colored Jeans Casual

LEVEL 99 PRIMROSE SKINNY JEANS – I love the color of these jeans – kind of between pink and coral, or primrose! Believe it or not, it’s a pretty versatile color. This was another Stitch Fix item that I loved and kept. These are super soft and stretchy. I’ve paired the casual style with a white tank and gray cardigan (both Banana Republic). The shoes are my gray camo Rothy’s. These shoes are AMAZING! They come in the point style that I’m wearing ($145) as well as a traditional ballet flat style ($125). They are like wearing slippers and are completely machine washable. Check out their story and, seriously, try a pair – they are worth the price.

Colored Jeans Dressy 2

I actually love the combination in this outfit and wish I had a place to wear it! The black satiny top (from Macy’s a long time ago) and the primrose color in the Level 99 jeans look elegant. The satin clutch and strappy high heel sandals (I swear I need to figure out a place I can wear these shoes) complete the pretty look of the outfit. I would definitely feel great wearing this look to a fun evening party.

I hope this tour of my closet (and my backyard!) has given you some ideas to try with your jeans – both casual and dressy jeans styling. Don’t be afraid to try something different and remember to have fun with accessories!


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