No matter how casual our everydays may be, having a dress, two, three, or even four that you can depend on for looking appropriate for the occasion, but also feel entirely yourself, is an absolute necessity. Nope, not a luxury. 

The tricky part often becomes knowing which dresses to buy that you can wear year after year and not look dated. 

I’ll admit, I have gone through my share of dresses, BUT, I also have quite a few dresses that I purchased over 10 years ago that I still wear and love. They are timeless. In today’s post, we’ll talk about what details to pay attention to that will ensure this timeless quality. 

Just a reminder that in our series, and thus in today’s post, we’re going to focus on everyday dresses, not special-occasion dresses. Focusing on dresses you will wear to work, to social get-togethers with family and friends of all types – indoor, outdoor, winter, summer, and in between. Dresses you will want to wear while traveling to stay cool as you peruse the farmers’ markets in the Provençal heat, but that you will want to wear when you return home when the temperatures soar. You get the idea. These will be dresses that you love, and that love you right back because you look great in them, and YOU wear the dress, the dress doesn’t wear you. 

But first!

How did you do on your task from Part Quatre/Four? Have a look below as a reminder:

Part Quatre Wardrobe Task

Take your measurements. Then, determine which style/design of button-down shirts you feel most comfortable in and that you need in your wardrobe to provide more options with what you already have or will be adding during this 12-month wardrobe project. Peruse the brands above to determine which brands speak to you, and even save the ones you would love to invite into your closet. Do this no matter their price point. Put the ones you have chosen on your KarmaNow list of favorites so that when/if they go on sale, you can check whether the new price works in your budget. Either way, you have begun to clarify what you love and what would work for your everyday life. And keep in mind, when it comes to button-up shirts, when you find what you love and fits you well, it is a great idea to buy multiples of that exactly item as they are separates that get mixed and matched with so many different pieces, and often are not the star of the outfit, but are necessary to complete a polished ensemble.
 

Before we dive in, I have some exciting news! There is a new, updated page for what used to be called the Capsule Wardrobe page here on TSLL. Now titled the Lifetime Wardrobe page (find the link in the drop-down menu under ‘Shop’ just below the blog header), you will find this series organized for easy perusal should you want to return to any of the posts, along with the most recent Spring and Fall Annual Shopping Guides, and finally, below the shopping Guides, you will see the continually updated Shopping Finds of clothing and accessories I recommend, love, and offer timeless style. Check out the page here. 

If you are new to our series, be sure to read Part Une/One as it details the full approach, which is an approximately 12-month-long wardrobe project, buying one (sometimes two) items each month, adhering to the list that we have created of about 12-15 items.

Now to Part Cinq!

Today, we’re going to explore the many different styles of dresses available, take a look at what components to consider to ensure a timeless purchase, where to shop to find what you love, and I will also share with you the dress I added to my wardrobe as I moved through this project. Let’s get started!

Part Cinq: Dresses to Flatter Your Silhouette And Style

Where to begin — Know Your Physique’s Strengths

When it comes to choosing a dress, having them in our closet, ones we love, makes getting dressed super simple. A dress is the entire outfit: one item of clothing, maybe we add a layer over our shoulders, and then, of course, accessories, but the clothing decisions are far simpler when we choose a dress. But we need to know which dress styles will make this feeling possible.

A dress works best when it is tailored to your body’s proportions. This sounds obvious, and no, I am not recommending going to a tailor to have a bespoke dress made, but you absolutely can do that. What I want to bring to your attention is that we each need to know which part of our bodies we want to bring attention to and which we want to camouflage or leave alone.

FIRST: 

Assess what parts of your body you feel comfortable choosing as the silhouette. Now, I am choosing my words very carefully here because I don’t want to say ‘star’. After all, you – the human being wearing the clothing, are the star – your being, your self, and all that you offer in your words, actions, and heart. Remember, your clothing is here to support you, not objectify you. 

Consider the following:

• Visage – face
• Long legs
• Narrow waist
• Arms 
• Shoulders (broad, narrow, etc.)
• Neckline 
• Back
• Calves
• Toned legs
• Hips 
• Hair 
• Bust

Notice, we’re focusing on what we love first. But we also want to think about what we don’t want to accentuate. However, I do think it is important to focus more on what we love, because it is amazing how, when we find an item that flatters a particular part of our body, we forget about what we may not like as much. It is all about drawing the eye, whether with a style created by a drape, a seam, or a pleat, the fabric’s print, texture, and weight, and many other details that, when done well, work with our bodies to bring our attention, as well as others, to what works best for us. 

SECOND: 

Determine your body’s proportions. Where does your body break into thirds? We don’t want to cut our body in half with the clothing we choose, so where do the thirds fall? If you have long legs, it’s likely that your waist is in the top third. This helps tell you that your legs may be one of the body parts you want to accentuate, or maybe it’s your waist. Either way, neither, you know that one of your thirds is your waist. This isn’t the case for everyone, and that is why we often will create the illusion of a high waist to elongate the leg if that is what we want to bring attention to. 

THIRD:

What is your body’s shape? 

Macy’s does a great job in a detailed post breaking down the four different, classic body shapes – pear, apple, rectangle, and hourglass (they also explore slim, athletic, plus, and petite) – so I won’t repeat what I have a feeling you’ve read about every time you pick up a style book. But what I will underscore as important is knowing your body shape or what it most closely resembles. If you, like me, find yourself fitting into more than one, even three, then don’t fret. Simply understanding your body’s stature and how certain items will accentuate certain features is helpful knowledge to have – for example, I don’t necessarily want to purchase any shirt, sweater, or blazer with shoulder pads as I already have broad shoulders, but having a nice square angle at my shoulders does sharpen and elongate my entire silhouette, so finding the balance is helpful.

Types of Styles to Consider

Why we want to do our personal silhouette homework (above) first is that it will help us eliminate certain dress styles immediately, narrowing down our choices and helping us find the dress that suits us best more quickly. Once we most the distractors, we get closer to finding the treasures that will both catch our eye and look good on our physique.

The key really begins with knowing what you want to accentuate. For example, if you have an hourglass figure, and you want your hips to be noticed, a body-con dress is a wonderful option. But on the other hand, maybe you want to play down your hips and focus on your waist or shoulders instead, your dress choice will be entirely different, with a full skirt and flattering sleeve length that brings the eye up. 

Let’s take a look at how we can narrow down our search simply by knowing the terms to search for when we shop, and what to ignore as well:

Lengths:

• Knee-length: Just as it sounds! ☺️
• Midi: a hemlength that falls between the knee and ankle, often, mid-calf, thus the name
• Maxi: a hem length that falls near the ankle.
• Mini: While this is typically not a lifetime option, worn with tights or nylon, or if you have killer gams, this is the dress to consider as the hem-length falls mid-thigh.

The various style terms of dress types:

Below are the types of dresses often worn during the day or evening, but not for special occasions.

• A-line: appears as the silhouette of an A as it is narrow at the hips and widens toward the hem. 
• Bodycon: Silhouette fitting from shoulder to the hem that is usually a knee-midi length. Dresses are usually made with a stretchy material.
• Boho/Bohemian dress: Loose, flowy, and often features bohemian patterns, ruffles, sometimes lace and other details such as embroidery. Lengths vary, but many are longer.
• Halterneck dress: the name speaks only to the neckline, as the rest of the dress could fall under many different dress categories.
• Pencil/Column dress: the dress from the waist to the hem is narrow and straight, fitted similar to a pencil skirt. Sometimes these dresses have a blouse-like top of the same color, others have a structured button-up style or zipper closure. Sometimes, the top is a different color from the bottom.
• Peplum dress: Anne Hathaway wore a handful of versions of this traditionally styled to have short, gathered, or pleated strip of fabric attached at the waist, and a narrow column shirt. Check out her voluminous striped Louis Vuitton version here, and her more classic one made by Stella McCartney here.
• Shirt dress: Resembling a classic button-up collared shirt, often with a belted waist, lengths can vary from above the knee to maxi.
• Shift dress: loose and hitting above or at the knee, they hang from the shoulder to give it their swing, sleeve-lengths vary.
• Sheath dress: A tailored, close-fitting dress that falls to the knee or midi-length.
• Slip dress: think the 90s – CBK, Kate Moss, looks like a chemise or underslip with thin straps made of silk or satin fabric.
• Sweater dress: coming in a variety of styles, most are body-on, wrap or column.
• T-shirt dress: a casual dress often made of jersey, slub, or a blend of cotton for a comfortable fit, various lengths, short sleeves, and looks like a t-shirt.
• Wrap dress: provides adjustability, so long as the neckline closes to a V for your comfort preference. A front closure created by wrapping the dress around itself and tying at the waist.

An Investment Worth Making: Which Details Make a Dress Timeless

Fabric that will last and have the opacity that you feel most comfortable wearing

There are many different types of fabric to consider, and blends are wonderful when it comes to dresses for the proper draping, texture, weight and to ensure proper coverage. Feel the fabric. Will it last multiple wears? One of the many details I appreciate about the dress I will share with you below that I have added to my wardrobe is that it is a sturdy fabric that will last, but it’s not too heavy either. The perfect balance.

Of course, natural, breathable fabrics are a dependable choice (cotton, linen, cashmere, silk, chambray, but with casual, everyday dresses, blends are helpful for a bit of stretch, a beautiful drape, or a touch of shine – satin, for example. However, for investment purposes, if you stick to natural fabrics, and as we will discuss below, the construction is high quality, you will have the dress for a good long time.

Look at the seams

You want sturdy seams, so either French seams or bound seams instead of a basic serged edge. This detail will ensure your dress lasts and maintains its proper shape. What’s a French seam? Brought to us from the world of couture, as fancy as they sound, they aren’t difficult (or so I’m told) to make, so for the shopper, it’s worth making sure your dresses have them because “they wrap the raw seam allowances in fabric, creating a smooth, beautiful finish on the inside of the dress.” Here’s a tutorial with visuals.

A bound seam also creates a beautiful interior finish by taking the raw edges of a seam allowance and encasing them in a separate strip of fabric to prevent fraying and add strength. There are various versions of a bound seam, but the idea of using a separate strip of fabric straddles all of them.

Look at all of the closure features – zippers, buttons, ties (wrap dresses) – do they align properly?

Just because it looks like it has what it needs – a zipper, buttons, and matching holes (do they line up and is the spacing correct?), the loops and holes for the wrap dress belt to move through – doesn’t necessarily mean it aligns the way it needs to to hang properly on your body. Also, check the quality of these items to make sure they are secured well.

As someone who is broad-shouldered (mentioned previously), there have been many times when I have tried on a wrap dress, and it just wasn’t going to happen. No matter what size in the vicinity to fit me reasonably, it wouldn’t close enough to be able to move comfortably.

Stitching – how many stitches per inch?

You want more stitches rather than fewer. In other words, a high stitch density. This will give you durability as the seams will remain tighter and stronger. Also, look at the stitching – they should be straight and flat (no puckering) and no loose threads.

Lining quality

While not every dress will have a lining, if it does (and you want it to), look at it closely. It should make the dress more comfortable to wear as well as help the dress drape beautifully (no sagging or bunching). The lining should also be breathable and not make the dress heavier than necessary.

Check the internal structure pieces

Similarly to the button and zipper alignment above and how well they are made and if they are properly placed, check that all the internal details that provide the proper fit are in place, securely attached and will last multiple wears. This could be an attached belt, internal structuring, etc. Most day dresses likely won’t have too much internal material, but just in case they do, always take a look.

Lastly,

How do you feel when you wear it?

Can you move with ease? Can you sit down without a worry of ripping something? Is it so comfortable that you forget you are wearing it and can just go about whatever you are doing?

Sometimes, we buy a dress because we want something to happen outside ourselves when we wear it. This could be any number of things, but what I have learned, having made such ill-guided purchases in the past, is that I will always be the one wearing the dress. I finish the look. So I need to feel comfortable wearing it, and so long as I can just be, just do what I need to do without fidgeting with the dress, then I know I have found a dress I will love, and wear for many occasions and years.

The Dress I Added to My Wardrobe During this Project

In Part Une of this series, the steps for creating our list of 12-15 items were shared. Be sure to check that post out. You will get a glimpse of my own list and learn how to choose the items you select.

One of the items on my list, as I assessed how to best fill the gaps, and provide what I needed for everyday and the outings I want to be prepared with an outfit that speaks to my signature style, but is versatile enough to suit many occasions, while also being timeless, was a midi-length long-sleeve dress.

My preference is a collared dress, a V-neck, not too tight a top, but a more fitted skirt, and midi-length. I then wanted a color that wasn’t too dark, so it could be worn in multiple seasons.

I first saw Staud’s Scout dress this past summer, and saved it to my KarmaNow favorites list. The full price was a bit steep, but I immediately knew the style was to my preference. So, I put it on my list and waited to either see if it went on sale or I could purchase it full price.

November arrived, and I discovered the dress was out of stock, no longer available in my size. Oh well, at least I tried, and finding it helped narrow down what style really caught my eye as I continued to think about the dress throughout the autumn months, which, for me, is a sign that I really do know it is my style, not just a passing trend that catches my eye and then I forget about it.

Then, much to my surprise, I received an email in late December/early January from my KarmaNow alert of a sale on my saved item. The Staud Scout dress was on sale and in my size! What! I was completely shocked, and funnily enough, when I went to the site (not using the link through Karma), the dress was no longer on the site. BUT through my link that I had saved, it was still available!

This is a lesson I also want to share: Sometimes online shops reorganize their sale pages, main pages, and search terms. When they do this, older items will often get buried and be unable to be found unless! We have the original link that we saved earlier. This is exactly what happened in this situation. I wasted no time, as I hadn’t found a dress to replace this one that I had originally placed on my list, and I scooped up the dress, saving over $150.

Why I love this dress:

• An adjustable waist: It’s hard to see, but there are side belts that can be loosened or tightened to cinch the waist and create a blouser effect with the top.
• Adjustable neckline: I also love this for being able to fit my physique perfectly and no gaping (as would be the case with buttons).
• Long sleeves that can be pushed up, rolled up, whichever suits the occasion
• The blouse top is oversized enough that you can wear a shirt underneath – a turtleneck in the winter, a crew-neck striped tee or brighter color, the options are many.
• The fabric is super lightweight and comfortable against the skin.
  • This also makes it easy to pack and steam for travel.
• The grey isn’t too dark or light – just right; and is a perfect neutral giving me many different options of shoes or boots I can wear with it.

Once we know which colors, styles, fabrics, and lengths look and feel best, we may find that over time, we have a good handful of dresses for cold-weather and warmer weather. If you take a look at my dresses below, my preferred color palette is evident, and you will also notice I have a few of the same exact dresses, but in different colors – my two sweater dresses, for example. Stripes are a favorite, but then too are my neutral solid colors.

Three of the dresses I have had for over 10 years, and the Staud dress is the most recent addition. The previous most recently purchased dress was purchased two years ago. I also have a few linen dresses and cotton shirt dresses that I wear exclusively in the summer months. For the most part, the dresses you see below are for winter and the shoulder seasons of spring and autumn.

Where to Find Dresses You Will Love for Years

When it comes to dresses, just about every brand will offer a new dress, a new style, new colors, etc., each season. Unlike jeans or shirts, my dresses come from a wide swath of brands.

Of course, shop your favorite brands, but then shop at department stores or boutiques (online or in-person) whose sartorial tastes you love. They will make available a wide range of brands, often in a similar style or taste you love, and maybe introduce you to new designers you didn’t know about who create what you prefer to wear.

The key is to know what looks good on you, and to look for quality craftsmanship. Look inside the dress, try it on, and don’t be afraid to return it if you order it online.

Lastly, if you love a dress, the fabric, the style, just about everything, but the length is too long, or the slit is too high, or the size is too large, these are all (for the most part) fixable with the help of a tailor. I have three dresses in my closet that I simply took to a local tailor and had them either shortened or close the slit because I loved the rest of the dress. I am so glad I did this because when we find what we know we will wear, it is sometimes just a small tweak away from being perfect.

In the monthly Outfits of the Month posts, often dresses are included, and in fact, tomorrow’s May’s Outfits of the Month will include a few dresses for late spring and summer. But first, here’s your homework for this month before you start shopping for the dress or dresses you need in your everyday wardrobe:

1. Determine which or what physical part of your body you want to bring attention to and which you want to minimize or not accentuate.
2. Take a look at the list shared above of the various styles of dresses. Which style would help you achieve your goal of looking and feeling confident?
3. Once you have narrowed down the type of dresses you are looking for, this will help you refine your online searches and save time when shopping in stores.
4. Similar to Part Quatre and Part Trois: Know the colors and various prints or stripes that would flatter your skin tone, hair, as well as eye color.
5. Decide for what recurring occasions you want to have a dress available in your closet that you can depend on to wear.
   • Examples: work, presentations, interviews, weekly family gatherings, evenings out with various people, different types of outings for fun, outdoor activities – markets, beach, lunch, brunch, etc.
   • Reflect back over the past year or two and try to recall when you would have loved to have worn a dress, or did wear a dress, but it just wasn’t what you had hoped you had in your closet. Think carefully about what you would have preferred, and then be willing to purchase well, so that forever moving forward, that dress will be in your closet and when you wear it, you will feel your best and be able to enjoy yourself fully engaged in the moment without giving a thought to what you are wearing.
6. Now begin to peruse your favorite brands, and save any that fit your above criteria to KarmaNow.

The Series Continues!

The series, How to Build a Wardrobe to Love and Live In Every Day, continues with Part Six next month on Tuesday, June 9th. 

Between now and then, tend to the personal style assignment above, and then be patient, that spring dress that catches your eye this season may not go on sale until July, but at least you know that if it does, you will want to wear it year after year, and it isn’t just a passing trend.

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