Casual Dressing with Jeans

I grew up wearing a uniform to school every day and I loved it. Once a month we could dress up and show our creativity, but I loved the everyday speed of throwing something on and not having to think about it.

 

This uniform dressing experience strongly influenced my approach to style. Studies show the average woman spends 45 minutes a day trying to pick what to wear. This is just a meltdown in the making, and stress no one needs. Having said that, what I do for clients culminates in their having key pieces that can easily be put together creating many fabulous outfits. There is no room in your wardrobe for pieces that fall into the mediocre category; you should be absolutely in love with everything in your closet.

 

BOTTOMS

 

Skinny & Flare-leg Jeans

These are absolute essentials in your casual dressing wardrobe. Both cuts are “must-haves” and make sure that you have variations of them in a variety of denim, color, distressed, etc. Not only do they need to be in your closet, but they need to be a substantial part of your casual wardrobe.

Khakis

After jeans, you may want to bring in khakis—skinny or baggy, you can’t go wrong. Pair your wide-leg pants with sneakers or sandals. Both flat and clog-like are fabulous, and a great look!

Shorts

I’ll include shorts in this list, but be sure if you’re wearing short them, you’re young enough to carry them off. If your legs aren’t your best feature, wearing short shorts is inappropriate. Style is here to suit and serve you; not the other way around.

Many of my clients love the longer Bermuda or city shorts—they’re often more comfortable and flattering to the body. They are also definitely a stylish alternative to shorter shorts.

Flirty Skirt

Let’s not forget the flirty skirt! This silhouette can be worn as a mini if you are young and at knee length, once you are in your 40s. It’s a wonderful summer piece and worn with a t-shirt, and strappy sandals, or even a flip flop, this look can be a real winner.

In the winter months, I only recommend this for the younger set unless you are dressing up… and in this case, we are focusing on casual looks.

Casual dressing with skirts and khaki pants

TOPS

 

White & Black T-shirts

Next, we’re going to look at tops. When dressing casually an item that needs to be in abundance in your closet is the white t-shirt.

I am a big fan of the crew neck, but if you have a round face or short neck, you may prefer to do a high v-neck. It still needs to cover everything so no plunging v, but this neckline does give you some length in your neck and face.

Possible sleeve lengths include a short sleeve, long sleeve, ¾ length, and sleeveless depending on your arms.

In terms of length and silhouette, you may consider longer, fluted, and tunic-style tees. You can also do short tees, but stay away from the stomach-baring variety, which is neither tasteful nor stylish. The asymmetrical fluted t-shirt is currently the flavor du jour and it very flattering to every body type.

Another item you could include in your wardrobe is a black t-shirt. A few black t-shirts are good to have and can change the looks you are putting together, especially for casual nighttime looks.

White Crispy Shirts

Another top that is a fabulous, versatile keeper is the white crispy shirt.

As far as length goes, I recommend longer shirts that fall below your backside, but no longer than mid-thigh depending on your height and what you’re going to wear with it.

These aren’t always readily available, so keep your eyes open for them. I sometimes go a year or more and don’t see one that is worth purchasing, so again, keep an eye out for a good one.

Chambray Shirts

And then there’s the chambray shirt which comes in all sorts of silhouettes. You can do a vest that you wear over a white t-shirt, a jean jacket, or a traditional button-down. Everyone needs one!

THIRD PIECE

 

Cardigans, Jackets & Blazers

Now it’s time to talk about the all-important third piece.

Cardigans are a great piece that you’ll need… along with the previously mentioned jean jacket. In terms of length you can go anywhere from long cardigans (as long as mid-calf or mid-thigh) that will give you length and make you look slender and can be worn over your t-shirts and jeans to cropped, shorter versions that can be worn layered with a longer t-shirt.

Jackets are another great third piece. You can also do blazers, but don’t get too preppy. Keep everything casual, relaxed, and fun.

SHOES

 

Booties, Clogs & Sandals

There are an amazing number of looks from which to choose where your shoes are concerned. I’m seeing fabulous suede and sandal-like booties that would go great with your jeans—I’ve recently seen white mule booties that are to die for! And some of our favorite 70s looks, like clogs and clog-like sandals, will be a wonderful addition to your shoe wardrobe.

Flip Flops

Nothing says “casual” quite like a flip flop. When it comes to flip-flops, I am only a fan of plain, unadorned styles—no sparkles, no jewels. Tkees are a great brand to look for.

Sporty Shoes

Another style of shoe that is perfect for this look is the sporty shoe. The slip-on sneaker (called the skater), Converse sneakers, and even high tops if you do them right, can add some fun edge to your look.

Oxfords & Ballet Flats

And last, but certainly not least, the oxford and the ballet flat (pointy or round) are wonderful pieces to round out your wardrobe as well.

ACCESSORIES

 

Now really all you have left are accessories. I suggest link bracelets. If gold is available to you then fantastic! You want to stack these things, so you need at least two, and wear a watch.

Mixing metals is great, and a big-faced watch is essential. Since this is casual, go for the fashion watch. Remember that odd numbers in decorating are the thing, so go for three or five pieces, but never two or four in total, including your watch.

NO necklaces in my opinion. They simply detract from the overall look and can come off as cheap or trashy.

For earrings you can go with anything—hoops, chandeliers, just have fun!

Unless you can’t get your colors to compliment, and notice I am saying compliment not match, all of this will go back and forth together. You literally can just walk into your closet, grab some bottoms, and pick from the rest.

SAMPLE LOOKS

Below are a couple of looks that you could quickly pull together base on the suggestions I’ve mentioned above:

Look 1:

White, wide-leg pants, Converse sneakers, white t-shirt, chambray shirt open and over the t-shirt, or use your denim jacket. Black t-shirts or striped t-shirts work great as well. The length needs to be short. Great bracelets and earrings and you’re ready to rock and roll.

Look 2:

If you’re in the mood for jeans, go grab your skinnies or flares in any color, pair with a white t-shirt and one of your cardigans (preferably in a longer length), and a shoe—anything from booties, flip flops, or ballet flats to sneakers or clogs—they all work beautifully! Combine any of these pieces together, and again, you’re ready to go!

Look 3:

If you want to do a skirt, pair a flirty skirt with a white t-shirt and add a shorter or cropped cardigan around your waist OR wear a denim jacket and grab your flip-flops (or mules, ballet flats, clogs, strappy, or platform sandals) and you’re good to go!

NEUTRALS VS. COLOR

I’ve suggested items you’ll want in your closet to make this all work for you, so just keep in mind if you stick with neutrals, it makes it easier to mix and match your looks.

We ARE talking casual clothing here, however, and color is a big deal. Feel like combining yellow jeans with royal blue shoes? Go for it and have fun!

BUDGET RIGHT AND SHOP RIGHT

If you play by these rules you never have to worry about emergency shopping! Think of building a wardrobe as a journey, not a sprint.

THREE CHEERS FOR “UNIFORM” DRESSING!

This gives you a number of ideas on ways to employ the “no-stress express” system for your casual looks. It is basically uniform dressing that will create variety in your wardrobe, make you feel chic, and take you no time to get dressed.