Ask Allie: Stylish Casual Summer and Spring Attire

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Hi Allie:

I need some advice about my spring and summer wardrobe. I am a curvy, petite 41-year-old and look best in tailored clothes. For work, I tend to wear classic pieces with a vintage twist and black is my neutral. Casual has always been harder for me, and therein lies my problem: while I am able to come up with a small summer work wardrobe with light weight versions of what I normally wear, I am lost when it comes to casual. I don't like the boho styles that tend to dominate summer, I don't look good in florals, white near my face is awful, I HATE pastels, and I am constantly disappointed by the quality of lightweight T-shirts, which aren't that flattering on me to begin with. I don't wear tank tops and capri pants make my legs look chopped off. I need some direction! Can you help?

I know by looking at stores’ summer collections you would feel like the minority, but you wouldn’t believe how many similar emails to this I receive. Not only that, I hear this same rant from my mom, who has a classic, clean personal style and isn’t one to wear boho styes, flowers, or pastels. Here’s some suggestions:

summer fashion

City or Bermuda Shorts. Just a few years ago, it was mid-thigh shorts or capris with nothing in between. Then around 2008 the City Short became a popular piece, often creating a summer short version of a suit. Not only that, Bermudas and City Shorts started coming not only in slightly varying lengths, but also leg widths. This meant if you had thick thighs you didn’t end up looking as though you were wearing bike shorts, and if you’re not a true petite or tall, you could find a flattering length without requiring alterations.

A pair of white shorts in a heavyweight cotton twill is amazingly versatile and surprisingly flattering. Paired with black and a pair of heeled sandals, such shorts are perfect for an evening barbecue or summer party. Wear with a brightly-colored tee and tan sandals for trips to the market or mall, and wear with a silk blouse and metallic sandals for an ensemble appropriate for a bridal shower or a creative office environment.

Other neutrals like black, khaki, ivory and olive can also be fabulous, but can look a bit extreme if you are petite, curvy, or pale. Be very aware of fabrics, length, and width to find a style that will fit and flatter your frame and personal style.

Midi Skirts. A softly gathered or pleated skirt in a lightweight cotton or gauze is a fabulous summer wardrobe addition. Pair with a fitted tee and flat sandals and wear anywhere from the mall to the farmers market to happy hour and even Casual Friday. Make it work with your personal style by adding accessories. Take a simple white scoop tee and black skirt – with a neon skinny belt and wristful of colorful bangles it is a trendy ensemble; with a brown wide woven belt and wooden bead necklace it’s boho; with a fitted colorful knit blazer it’s a great workplace look; with big silver hoops, a wrist of silver bangles and a gauzy oblong scarf at the neck it’s artistic.

Midi skirts give you the freedom to sit in the grass, hop on a bike, chase after your toddler without having anything exposed, but has the airflow missing from maxi skirts. In a lightweight fabric it’s comfortable on the most humid of summer days and gives a vintage feel without being too twee. By pairing with a simple fitted tee it’s not too dressy for weekend activities.

Maxi Dresses. I’m sort, I’m curvy, and a lot of fabric makes me look even more short and curvy. However, I do love me some maxi dresses come summer! Anywhere from below the knee to the ankle bone, I am a fan. The way I make them work is by choosing lightweight fabrics, and have them pretty small on top. I know you don’t like tanks and I can relate. However, I find a halter or spaghetti strap to be more flattering than tanks. Last summer thanks to a professional bra fitting, I found a strapless bra as comfortable and supportive as a regular bra and it opened up my casual summer fashion options. I also love the look of a big floppy-brimmed sunhat with a maxi dress – the hat really balances out the fabric of the dress and it distracts from the upper body.

Tee Shirts
A quality tee shirt in fun colors is hard to find. Many brands I found to be tee shirt Meccas have changed their fabric and cuts (hello Old Navy and J. Crew). However, these brands have proven time and time again to have a great choice of colors and styles made from quality knit.

  • Talbots – Talbots does a fantastic job of creating tees and knits that are classic, yet never boring. Strategically placed ruching and pleats, unusual necklines, multiple lengths and cuts of sleeves, petite and plus sizing means there is a tee shirt for most anyone.
  • Ann Taylor – I know I know, I am always preaching Ann Taylor. One wouldn’t think of Ann Taylor for basic tees, but they know how to do them well. In 2008 I was heading to a Washington Nationals game and wearing the opposing team’s color. I hopped into Ann Taylor hoping to find anything in red, navy, white or even black to show my team spirit. I picked up a red crewneck tee… and that tee became a favorite until it became too big. Because it became too BIG, not because it faded, shrank, stretched, or got icky over time. I washed and dried and wore that tee shirt for two years and it still looked great when I donated it. Since then, I look to Ann Taylor each spring and summer for standard tees. While they have creative styles with fun necklines and details, they also do a great classic v-neck, scoop, or crewneck tee in fantastic on-trend colors that are anything but boring (and there are very few pastels in the bunch).
  • Lands’ End – Lands’ End consistently makes high-quality knits in flattering styles. Each year they update their silhouettes and color choices. I wrote about many current styles here, but they have even more options online and in their catalogs. Also check out Lands’ End Canvas, a more youthful and trendy version of Lands’ End with the same quality and customer service.

Non-Tee Shirt Shirts
While tee shirts are an easy casual choice for summer fashion, there is more to life than short-sleeved knits. Here’s a few of my favorite summer styles of shirts:

  • Thin Cotton Tunics. Made of linen, thin cotton, or gauze, a tunic with sleeves can be even more comfortable in the heat then a jersey tank. They breathe, they catch any breeze, and they are usually pretty easy care (and actually look good with a few wrinkles and creases). While many can look pretty boho, there are many that can be quite classic and polished. This linen tie-front top from J. Jill has clean lines that would look great with dark jeans and flat sandals, with crisp Bermudas and a low wedge, or even tucked into or belted over a skirt. This roll-sleeve tunic from Gap has a great self-belt that hits at the smallest part of a woman’s torso, slimming and elongating the frame. I like the detail on this embroidered linen/cotton tunic from Eddie Bauer, and think the Vintage Blue or Sable would look smashing with white jeans and metallic sandals for evening, or a pair of faded denim or white shorts for daytime.
  • Striped Tops. If you’ve taken even a quick glance at my outfit posts, you know I adore stripes. While many think stripes widen a figure, I find them to distract the eye, and they are a cheap and fun way to add a current trend and a bit of pattern into the wardrobe. Stripes can give a preppy or nautical touch, a French Chic feel, or even a rocker vibe to your wardrobe. This pieced stripe tee from LOFT is a change from the typical knit top, and the color story would look amazing with black, denim, khaki, or an unexpected bright like orange or green. The short sleeve Breton top from Boden comes in a variety of fun colors, and has a wonderful feminine cut to it that makes it look anything but ordinary.

And now I ask you brilliant readers – what are your favorite wardrobe go-to pieces come summer? How do you stay cool and chic in the heat?

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  1. this post is so useful. Currently due to the climate of where I live my summer wardrobe is  basically my winter wardrobe minus the coat, however I am moving abroad soon to a much hotter climate and am at a loss as to how to dress. I bought a couple of maxi dresses and was looking for maxi skirts, but I think after reading this I’ll try finding midi skirts instead. I like the idea of mixing plain items and making it fancier with light accessories- it will save on suitcase space! Gotta find some quality t shirts too- its hard to find affordable ones that aren’t thin, see through cotton or worse, polyester D:  thanks for this post!

  2. When I go to Bonnaroo I LOVE midi and maxi dresses – they are boho enough for me to fit in, but can be clean enough of a style to still feel like “me.” I find nice cheap ones at Ross every year that can handle some mud and grime of a fest. Glad I could help – know it’s been a while since you wrote but I’m trying to catch up as best as I can! 🙂 Have a fabulous weekend!

  3. I DID write this question! Thanks so much for featuring it. These are all great suggestions. I like the outfits featured and that gives me something to work toward.

    The thing I didn’t mention in this question (because it was already so long….) is that every summer we go to a big hippie fair in Oregon and while I don’t feel any pressure to hippie it up (because anything goes with hippies) I do need a couple of things that are comfortable, able to get filthy, and cool – it’s much warmer there than where we live. I think the maxi dress is going to be my solution this year – I’ve avoided it until now, but I think that I can find basic enough styles that aren’t “too much.” The maxi in the picture is beautiful!

    Thank you, thank you, to you Allie, and to everyone for your advice! Glad to know it’s not just me.

  4. I could have written that question as well. I am currently vacationing in the US, (Myrtle beach to be exact) from 2 hrs outside of Toronto and had tons of luck in Ann Taylor and The Loft outlet here (yeah me!) I am a curvy hourglass and 5’4″. the tshirts are great and I found a couple dresses, a little embellishment, ruching, just a tad fancier than at home, dresses it up a bit

    Also Chico’s had great capris with a cuffed hem that just fit me above the ankle bone…your stores here seem to cater to curvy bums 🙂 I am loving it…if I can only talk the hubby into stopping inErie PA

  5. Nope, and not a silly question at all! Spandex will help a knit keep its shape, but it isn’t required for a fitted or feminine shape. I have many tees that are 100% cotton and still have a great silhouette, many of the ones from Ann Taylor that I mention (including that red one) are 100% cotton.

  6. Allie,

    Sorry if this is a silly question. Does a t-shirt have to have spandex in it to be considered a ‘fitted’ t-shirt?



  7. The necklace is from – if you click on the image it will go to the Polyvore page for it and it has all the details. 🙂 I LOVE the idea of a chevron skirt! As for shorts, I have the best luck at Target of all places – last year I found two pairs there that were surprisingly flattering, a great price, and a perfect weight of twill. I have also found some at Gap in the past that I really like the shape of on my apple self.

  8. Allie – where is the necklace in this post from?  (The one shown with the turquoise blouse.)  I love it!  Great advice here.  I also want to suggest chevron striped knit skirts, comfy and not too fussy –  White House Black Market has a great maxi one, and Old Navy has midi chevron skirts.  Any particular suggestion on where to get shorts?  I’m apple-shaped, so shorts that fit on my tummy tend to flare out like a skirt on my thighs!

  9. Some of my summer staples are light modal knit dresses for casual days with flat sandals, camp shirts with bermudas and flat sandals or boat shoes, light cotton sundresses with a-line skirts, etc. 

    I am a big fan of linen as well! 

  10. Wow,  I could have written that question myself.  Your reader perfectly echoed my summer casual challenges and style preferences.  Allie, I love the outfits you posted and your suggestions and would like to add a few additional suggestions.  I have, for the first time ever, made a concerted effort to create a summer casual wardrobe that I don’t hate..and doesn’t make me pray for a quick end to the summer months.
    Susan Graver (QVC) makes a number of lovely “classic, basic” T-shirts in “butter knit” fabric.  They are very durable and the colors are beautiful and style variations are great (bateau neck, V neck, elbow sleeves, short sleeves, 3/4…too many combinations to name.  They wash and wear well, are comfortable and look more polished and classic than cotton T’s.  They are a bit pricey, but the are economical when you consider cost per wear and durability.  They run in the BIG side…so size down.
    I love summery pencil skirts with stretch.  A floral skirt with a solid top may be a good solution.  I never wear florals on top…not a good look for me; but a skirt in an abstract, watercolor floral works well.  
    I am very, very curvy on the bottom..a true exaggerated pear; and I have found that well fitting ankle pants work very well!  I found a great pair at Dress Barn in the Jones line in hot pink, white and black.  Never thought I could wear hot pink!  I also found a beautiful green Calvin Klein pair at TJ Maxx.  I have always shied away from bright colored pants (and even tops) but these ankle pants look great and elongate my legs when worn with a stripy wedge sandal.  These are not skinnies.
    I don’t wear jeans often (almost never) but I did find a great pair of fairly lightweight curvy fit slim leg boot cut jeans with stretch at New York and Co.  They are one of their basic and they carry them most of the time.  I bought them in a dark wash and they are so comfortable and look great with a pair of wedge, platform sandals (or heels), and I can throw on just about any summer top and it looks great.
    A few knit blend summer dresses that are a bit more tailored also boost my wardrobe.  Calvin Klein’s summer dresses can be found at TJ Maxx; I have found numerous flattering styles there.
    It takes some work, but I finally have my summer wardrobe.  I hope my tips help.

  11. I second Ann Taylor t-shirts – they have a nice weight to them and hit at a flattering length to wear them untucked. If you hit a sale, you can pick them up as cheaply as Target or JCP and they last and wear so much better. 

    I’m not a big fan of long skirts, but I also have a few maxi dresses that are great for wearing on the plane, to a conference, or out to dinner. They are so much more comfortable than jeans, but also provide some warmth when faced with the always frigid a/c in Houston. 

    I’m also not a fan of pastels – but how about bright, saturated hues for the summer? I’m not sure where the OP is from, but tropical colors are huge down here and can be balanced with black to keep them from being too overwhelming. I’m also a big fan of a crisp shirt-dress during the spring and summer months. 

  12. First of all – the maxi dress you feature is GORGEOUS. Love maxi’s – especially that one!

    I found the best t-shirts at The Limited this season. They are heavier weight and not strictly t-shirts (a little nicer – more work appropriate) with beautiful scoop necks, longer (but not too long) length and perfect sleeves. They come in a TON of colors and I bought two black ones, a navy one and a fab black and white stripe one. Highly recommended. 

    In terms of shorts -I have never been able to find bermuda shorts that work on me. I carry most of my weight in my thighs and they never seem to do anything but call attention to that area. Wish I could find a pair that works – but until then, I guess I’ll stick with breezy skirts and dresses.

  13. For someone who doesn’t like boho and feels best in structure, what about a lighter weight camp shirt? The ones in (or was it last year?) – even ones i’ve found at Target – have sweet (and practical) buttons to secure a rolled up sleeve, either bracelet length or at the elbow. Even the ones in the “wrinkly” fabrics can stay that way – it’s summer, and it’s the weekend – who wants to iron!

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