Note: This post contains affiliate links. Thank you for supporting the brands that support Something Good.
I love jeans. I would spend most of my time wearing them if the world let me. Unfortunately, dress codes tend to get in the way of my love of jeans. However, I do enjoy showing people how wrong they can be about denim. In fact, when I was going to put together an outfit for this post, I was originally going to put together a simple outfit with a skirt. But instead, I figured that why not take this as a challenge? Why not instead use this as an opportunity to see how you can create classy looks from nontraditional pieces.
Everlane The Cashmere Wrap Sweater c/o
Aeo Jegging
Everlane The Day Boot c/o
Everlane The Form Bag c/o
How To Dress Classy
So let’s get into some of the Do’s and Don’ts of Dressing Classy First.
Do Wear Tailor, Well-Fitted Cuts
Do you know what the #1 trick is for the people who always look completely put together? They have their clothes tailored to fit them perfectly. When your clothes are perfectly tailored to you (not oversized, or super tight), you immediately look classy. Plus, you’ll feel confident when you know you look extra good.
Don’t Wear Anything Ripped
The epitome of classy to me? Coco Chanel. Would she ever wear something ripped? Nope. Now, do I own ripped jeans? Yes, yes I do, but do I wear them when I’m trying to keep it classy? No. They’re for my lazy days. If you’re keeping it classy, put away any ripped clothing immediately.
Do Pick Colors That Complement Each Other, But Aren’t Overwhemling
The nice thing about keeping it classy is that you can still wear your favorite bold colors, you don’t have to stick to neutral colored pieces (though I’ll almost always pick navy blue, haha). But, I would suggest sticking to one (or at most, two) colors to avoid overwhelming your outfit. If you choose to do two colors, check out my color blocking post for tips on to how to properly pick colors.
Don’t Wear Trend Pieces
Most of the time when we’re saying classy, it’s also a substitute for classic. So when you’re thinking of classic pieces to wear, avoid the trendier items in your closet. Some of them may work, but typically the super trendy pieces will not. Save them for another day.
Do Wear Simple Cuts
This also goes back to my point above about avoiding trend pieces. Again, most classic pieces tend to be classics because they have simple cuts that compliment most body types (like pencil skirts). And why wouldn’t you want to wear something that’s going to look good on you?
Don’t Hike Up Your Hem Line
I don’t think most women fully understand this until they start to get older and then all of a sudden feel really uncomfortable with their hemline halfway up their thighs. If you’re trying to keep it classy though, lower that hemline. Also consider raising your neckline. There’s nothing wrong with sticking to a little more to the conservative side and leaving them wanting a little more.
Don’t Pick Anything You’d Wear to the Gym
Ditch those yoga pants and leggings! I love my leggings. I would spend most of my life in them. But at the end of the day, they’re workout clothes. They aren’t the completer pieces for your outfits.
Do Pick Quality Clothes
In the opposite vein, start to consider investing in more quality clothes. Clothes that won’t rip as easily or end up becoming gym wear. These clothing might actually come with free tailoring or already be so great that you’ll want to pay to get them tailored so they look even better.
Classic Simple But Classy Outfits
For my primary outfit in this post, it’s simple for a few reasons. First, the denim works because I went with a simple dark wash. It has slim cut, with straight lines, so it wasn’t very distracting. Next, the cashmere sweater takes the whole outfit up. Most ballerina-style tops are quite often considered a classic style. Finally, the boots I’m wearing are a simple, elegant boot that adds to the outfit. I would feel comfortable wearing this outfit to work or on a date night.
This outfit is the embodiment of simple but classy.
This outfit is the embodiment of simple but classy. Here, I was able to incorporate a little black dress into a work look. I did this by picking a dress that was close to knee length and then pairing it with a low block heel. Then, I stuck to minimal accessories (only a scarf). I went with mostly neutral colors here, but I also added a pop of color for fun.
Seriously Dana, shorts? YES!
You can be classy with shorts, thank you for asking. What’s the trick? High waist shorts! It all goes back to what I said early about covering up a little more. The more conservative up you are, the classier you can look. Now, if there’s also one thing that girls in the (and Red Era Taylor Swift) taught me, high waist shorts don’t mean you have to sacrifice your fashion choices. Make it fun! Pick pairs with a cute bow, polka dots, or fun colors.
But I thought you said you can’t wear gym clothes, aren’t you wearing sneakers here? Thank you for pointing that out too. Don’t wear your ratty gym clothes. If you want to wear a tennis shoe, or sneaker, find a cute, clean pair! Notice how I picked out a CLEAN pair of converse? Check out Keds for cute pairs or one of the other billion brands that sells adorable sneakers that don’t belong in the gym.
This is still one of my favorite outfits.
This is still one of my favorite outfits. Also, one of my classiest (a favorite of the Capitol Hill moms, if I remember correctly). A crewneck sweater and a striped, knee length skirt. The sweater is well fitted and the skirt fits me at the perfect spots. It perfectly captures some of the points I made earlier.
Everlane The Cashmere Wrap Sweater c/o
Aeo Jegging
Everlane The Day Boot c/o
Everlane The Form Bag c/o
Photos by Heather Bien
