Easy Dresses for Every Season

Summer has just begun, but we must look forward to the upcoming seasons in order to make our wardrobe work overtime. In your closet, you may already have some easy dresses for every season that you've overlooked. Like that favorite summer dress you just can’t live without? If you could wear it all year long you would, right? With a bit of creative styling, you can! Layer and combine texture and pattern in an artful way to extend the life of your most cherished pieces.

The key to carrying over lightweight dresses into the colder months is to keep things simple. This can also work with heavily beaded dresses or cut-out dresses. To have the greatest success, a short body hugging dress works best as a base for your cooler weather accessories. Keep casual cocktail dresses, either in prints or in solid colors, in mind for this application. Easy dresses cut in simple forms and light fabrics make versatile additions to your closet.

Mixing it Up With Some Hot New Styles

Easy Dresses - Sherri Hill 50146 Strapless Floral Black and Pink Print Cocktail Style Sherri Hill 50146 Strapless Floral Print Cocktail Dress

Sherri Hill 50146 is a great example to illustrate how to pull this off. A bold graphic floral print doesn’t have to be confined to summer or spring. Since this dress has a strapless sweetheart bodice, it would go well with a solid color cardigan, solid knit stockings, and a pair of biker boots that hit just below the calf. This gives off a look that says sweet but edgy. Playing with contrasting textures is a great way to emphasize the best of each piece. The satin-like finish on the dress against a knit fabric can look sumptuous and rich. Depending on the color cardigan you chose, you can pop one color out of the floral pattern. A pale pink or a bold fuchsia makes for an interesting statement. Putting leather boots with this look makes it feel like fall, but keep them simple. The main focus is the pattern design on the dress. Neutral earth tones go well with this look. Deep blues or slate grays are colors that could pair well with this cocktail dress.

Faviana 7429 Perfect Lace Cocktail Dress is another perfect example of an easy dress for every season. Pairing lace with leather, or the look of leather, is a classic combination. Close fitting leggings with a leather look to them would work well here. Top it off with an oversized blazer with the cuffs rolled up and put on a black or white shoe and this look is ready for a brisk night in the city.

Faviana 7429 Black Sleeveless Short Lace Dress Black lace and leather accents make a classic statement

Even with Shail K. 3234 Beaded Cocktail Dress you can easily wear this beyond the summer. Just pair with a solid color legging and a cute shoe. Keep accessories to a minimum with embellished dresses like this. An open draping lightweight sweater or a long sleeve shrug will work well with this look.

Shail K. 3234 Cap Sleeve Cocktail Dress RissyRoos.com Go to a casual hang out or a black tie affair by changing up accessories

Make your Wardrobe Bigger without a Shopping Spree

Layering with your favorite dresses also adds great value to your wardrobe. Learning to wear certain dresses two ways or more cuts back on your dry cleaning bills. This is especially useful if you are traveling light. When I travel for work I can get away with one sweater, two pairs of leggings, one dress, two pairs of shoes and one tee and one pair of jeans and a baggie of lingerie for the whole week. The key is layering. You can wear a dress multiple ways without it looking tired. This opposite is also true, sometimes it can look like you tried too hard to make it work. Picking pieces in the same color family will help you mesh it all together. Have some variety in textures as well, this makes things fresh while ensuring that you have light weight and heavier weight options depending on the seasonal weather changes.

Wear a light slip in summer or pair with leggings and riding boots for fall. Loose cuts can be worn as a beach cover-up or belt it and wear a cropped jean jacket for a day out. Once you get the hang of it, layering works for everyone. It doesn’t have to be frumpy or haphazard. Having a plethora of accessories in different styles, like different cuts in sweaters, can bring a look together. Knit stockings, leggings with a metallic sheen or a leather finish, closed toe shoes from pumps to ankle boots to riding boots, have all these elements on hand to transition to the cooler months without sacrificing your favorite party dresses.

Going Casual

These principles also work well with your lower end everyday easy dresses. If you don’t have a small wardrobe of casual dresses, there are many places around the web where you can shop at any price point. Inexpensive dresses on thredup, wish, or choxi are great options for those looking for frocks to run around in on the weekend. Picking up friends for lunch, grocery shopping, playing with your kids, you need not opt for a plain tee and ripped jeans. A cotton dress can be worn alone with flats, or with a pair of close fitting dark wash jeans. If you look for easy dresses with a drop waist or an A-line form, you can wear them like you would a tunic top. This gives you the most coverage while maintaining your range of motion. It camouflages problem areas like the tummy and the thighs. Other alternatives are leggings with shapewear built into them already. Rhonda Shear makes leggings is fun prints with full coverage and tummy control. No see-through yoga pants here! Definitely take the time the night before to plan an outfit. Even if you are just going out for a few hours to get errands done. It boosts your confidence when you look and feel put together.

floral-dress-leggings-boots-layers-6 maegan tintari Layering in rust colors for Fall, Maegan Tintari via Flicker
Maegan Tintari Casual elegance with Creative Layering, Maegan Tintari via Flicker

A Few of My Favorite Things

Here is a sample of some of my favorite layering pieces I often use. Whenever I need some coverage on my arms or my middle, these are my go-to items:

Van Heusen is an established brand that you may associate with menswear. But they make the best lightweight sweaters for women in my opinion. It makes the transition to fall from summer effortless. One of my picks is a Purple Dolman Sleeve Open Front Sweater Shrug. The purple isn’t a deep royal purple, but a muted tone that looks more like a neutral slate color.

As previously mentioned, Rhonda Shear makes the perfect leggings. My favorite is the Charcoal Zebra Ahh Comfort Leggings. Yes, they are patterned. The colors are a deep gray and black, a muted tonal print that isn’t overpowering is a perfect item to use as a neutral. You could also wear these leggings as pants, with a short dress as a tunic top. These leggings provide great coverage, so no visible panty lines here! Plus they do double duty as my favorite pants to wear to yoga because they have a wide band of tummy control fabric at the waist. I find that it gives my core support, almost like a back brace but less constricting. It works great with black dresses that are either dressy or casual. I like wearing shift dresses over these leggings just because it’s an easy look and it is still on trend.

rhonda shear leggings These leggings are my favorite, full coverage and versatile
Black Semi Sheer Open Front Dolman Bolero Shrug Cardigan Jacket Sweater Top 2X eBay A simple shrug is a must for every closet





JustFab is probably my go to place for shoes. I love that they curate a collection for you. If you give me too many choices I won’t be able to decide! JustFab works well for my needs, and when I first joined up I got a BOGO offer. I purchased a pair of old school engineer style boots that remind me of a vintage style in black with silver buckles. I received them about 5 years ago and they still look great. In the fall, these are a staple of my wardrobe because they hit me mid-calf and are perfect for cooler weather or even in the rain. I’ve even slouched them to my ankle and worn them with a summer dress when the weather is warm.

Muted Neutrals

It is best to experiment with your look. Find out what works for you, what you are comfortable in, and then look for styles that are similar. Muted neutrals work well for most everyone. When you think “muted neutrals” don’t think “boring”. Think about dark navy, slate gray, dusty purples and rose hues are all muted neutrals. Classic elements in black and white are important staples to have in your closet. It’s the easiest way to look polished without exerting too much effort. Don’t be afraid to contrast textures, leather, and knit fabrics are warm and inviting once the cooler weather comes. These are also traditional menswear principles that have been leaching into women's fashion for decades. When you think about mixing patterns and texture, look to the masters: Ralph Lauren and Tommy Hilfiger have perfected this styling technique. Gain insight into these designers and their looks by exploring boards on Pinterest.

Some Important Things to Keep in Mind

Always get the size that fits. This is crucial. If it’s a size too small it makes you look uncomfortable and if it’s too big it will not conceal your problem areas, but instead it will make you look larger. You may be committed to a certain number size in your head, but try to get a fitting done by someone in the dress department of your favorite local department store or boutique. Associates are very knowledgeable and are there to help you. Even when picking out a dress like a shift or an open draped front sweater, make sure the fit is right in the shoulders and the upper back. Flowing fabrics in certain places are meant to look easy and effortless. If these types of garments are oversized, they can make you look like a laundry pile.

Know how to pair colors together. It helps to get familiar with the color wheel from grade school art class. If you feel apprehensive about mixing prints, put solid color accessories with a printed dress. This works best in the first example I gave you, big bold print dresses. Let the leggings and shoes be one color. This puts emphasis on the dress and doesn’t clash with the pattern. Make one thing the focal point of your outfit, and chose accessories of the same color to make that statement dress pop. Though these styles may seem more complex, they are actually very easy dresses to make viable for any season.

Shoes can bring an outfit to the level of either dressy or casual in a matter of minutes. A flat ankle boot in a black or mushroom gray leather would work great with a deep navy blue knit legging and Shail K. 3234 Cap Sleeve Cocktail Dress. Easy dresses, such as this one, are short enough to look like a tunic top, given the right fit on a taller person. Bringing this dress into casualwear is a snap, and transitioning over to evening is simply a matter of changing the boots out for a pair of pumps.

Easy Dresses Help Build The Perfect Wardrobe

Invest in key pieces that make you feel good. This may sound frivolous, but it is important to build a wardrobe on a few key items that fit you perfect and are of high quality. They don’t even have to be big brand names, but when you find something that is so very you, you know it right away. Take the extra time and money to have it tailored to you. If you don’t have a seamstress shop or a local tailor in your area, many department stores and dry cleaners can offer you that service.

Just because we are looking ahead to the fall and winter fashion lines does not mean putting away some of your favorite dresses just yet. A few key elements, paired with a bit of creativity, and you'll find that your cute cocktail dresses are easy dresses to extend the seasonal wear of the garment. All while keeping your look on trend and totally fabulous. From dining out on a cold night to running around with your girls on the weekend, layering is a great way to get the most versatility out of your closet.

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