Reader Request: Casual Shorts, Dressy Shorts

How to wear casual shorts outfits AND dressy shorts outfits

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Readers Carrie and Kelli had similar requests:

I’d love to find out how to wear shorts stylishly, both casually and more dressy, for spring and summer. And how plus-size women can wear them and look great.

Most of my thoughts on how to pick shorts that flatter your bod – including some recommendations for various heights and body types – can be found in this post on stylish shorts. So if you’re wondering which style to purchase and wear, start there! But if you’re looking for some ways to style your shorts for the season, read on:


Incorporating shorts into dressed-up looks is a fairly recent stylistic innovation, and many people still balk. If you conceptualize shorts as casual items only, that’s just fine. No need to force it. But if you’re interested in a few ways to craft dressy shorts looks, here are a few simple ideas.


Naturally, one of the best ways to dress up a shorts look is to wear shorts that are, themselves, a bit dressy. Printed, scallop-hemmed, embellished, crafted from dressy material, or paperbag-waisted like the ones shown above. There are a thousand variations for sale in just about every color, style, and size range. The bonus? Since the shorts themselves are already dressy, you can go for a simple, no-nonsense top and still look gussied.

Most appropriate for: Weekend wear, seeing friends


No, really! Just look how adorable! In my opinion, the shorts and blazer either need to match or be relatively close in color value. And since this is a summery look I prefer it with lighter tones, but black and darker shades could certainly work for evening. Now, just because the word “suit” appears in the descriptor for this outfit, don’t go thinking this is automatically work-appropriate. I’m sure there are employers who allow shorts, but I’ve never worked for any of them. In my book, a shorts suit constitutes a chic, dressy option for weekend and casual wear. Check your HR manual before wearing yours to the office.

Most appropriate for: Parties, dinner out, slightly dressy weekend events.


Now, I’m not saying that a red crew neck tee and red denim shorts automatically make a dressy ensemble. But pairing some classy shorts with a blouse in the same color or tonal range is both flattering and chic. A wash of unbroken color also gives you the opportunity to go bold with shoes, jewelry, or accessories.

Most appropriate for: Parties, dinner out, slightly dressy weekend events.


Again, trying this look with cutoff jean shorts will create an entirely different vibe. But supple rayon or silk ones, like those shown here, or simple, clean, plain, solid-colored shorts of any kind paired with a gorgeous blouse will look fabulous. Notice that you needn’t limit yourself to sleeveless blouses: The skin you’re showing by wearing shorts balances nicely with a more demure long-sleeved blouse.

Most appropriate for: Weekend wear, seeing friends, parties, dinner out


Undoubtedly, you’re familiar with the shorts-and-a-tee and shorts-and-a-tank formulas. And those formulas are both tried and true, so by all means employ them. But if you’re looking for some alternatives that allow you to flex your dressing muscles a bit more, read on.


Yes, you can wear your boots during the summer months! Pairing shorts with boots is a great way to mitigate any feelings of overexposure.  I recommend slouchy, perforated, light colored, and Western-style/cowgirl boots for shorts outfits.

Most appropriate for: Just about any casual activity


Are you thinking to yourself, “What’s the difference between a shorts suit and shorts with a blazer?” I shall tell you. A shorts suit generally has some level of matchiness between the blazer and the shorts; It’s more obviously a suit if they’re the exact same color, but like shades will do. A shorts suit also involves a blazer and pair of shorts that are made from relatively dressy fabrics: Tropical weight wool, silk, rayon, and the occasional good-looking twill.

But denim shorts, cargos, cutoffs, leather shorts, and all manner of casual bottoms can ALSO be paired with mismatched blazers to great effect. Since blazers are The Great Structuralizers, adding one to a shorts ensemble is a great way to inject some sass, class, and figure definition. Offset the dressiness with comfy sandals and a funky handbag.

Most appropriate for: Casual activities that don’t involve loads of running, lifting, or mushy messiness. So not ideal for taking your kids to the beach or helping a friend move house.


Here we’ve got another shorts-based monochrome look that skews casual instead of dressy. Why? It’s that darling collar and the sassy rick-rack detailing. And the fabric, of course. This casual cotton is far less formal than the silks and twills in the black monochrome outfit pictured above. If you love sassy details but worry about skewing young, just make sure to create balance within your outfits. Those peep-toe espadrilles keep this ensemble from veering into cutesy territory, as do the flattering fit and length of the shorts.

Most appropriate for: Just about any casual activity

Images via (in order of appearance) In Fashion Rehab, District of Chic, BET, Cupcakes and Cashmere, chictopia, Weesha’s World, Sartiography, the Snug Bug.

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details. Sustainable options are either used, handmade, made in the U.S., artisan made in non-sweatshop conditions, or made using sustainable/fair trade practices.

Originally posted 2011-06-20 06:11:32.

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30 Responses to “Reader Request: Casual Shorts, Dressy Shorts”

  1. Becca

    I love all these amazing pictures of these amazing outfits! I wore dressy shorts for the first time on Saturday (coincidentally my most recent post). I really enjoyed them – more than I expected to, as it happens.

    By the way, have I ever mentioned how much I enjoy your hair? I’ve liked all the incarnations – longer and how it is currently more cropped. Suits you to a tee!

  2. Katharine

    One thing about all these examples is that they are almost all too short for my taste… but we ARE in fact allowed to wear shorts to the office. (“Dress” shorts, in a length no more than 2 inches above the knee.)

    I generally prefer “skirtlike” shorts; I have a drapey pair with a wrap front, and I used to have quite a collection in a shape similar to the “shorts with a dressy blouse” example (I had a lovely pattern, and made them myself, back in the 90s. I wish I still had that pattern….) That style, with the shaped waist and A-line silhouette, is very flattering to the larger-size hourglass, I might add.

    Pleated shorts, on the other hand, tend to be even less flattering than pleated pants. I don’t really feel the paperbag waist, either (not good on a short-torsoed hourglass, folds over and looks bulky). I also need to be careful with slash pockets — very popular on shorts, and gap horribly.

    This spring, I bought the Gap “boyfriend” style shorts in the catsick ochre colour, and, among other outfits, pretty much duplicated the fifth from the left look in the SS Margaret Howell collection ( with my favourite (well, only) Tahari boyfriend blazer, a white silk T-shirt, and black Everybody sandals.

  3. Cynthia

    Heh. My “shorts wearing style” is “…and a t-shirt and sneakers”. If I’m wearing shorts I’m rarely fance-ing it up and creating a coordinated look. To me, shorts are for times when I’m just relaxin’ and don’t care much. I did buy some non-grubby bermudas last summer and sometimes I end up looking almost styled, I guess. Some weekend I’ll get my sh*t together and post a couple of shorts outfits.

  4. Patti @ NotDeadYet Style

    Great collection, Sal! I would so do the Queen’s look in a heartbeat. Those are the only shorts shown that are long enough for *my* personal style. But I also love looking at the shorts with boots – very cool – and the shorts-with-long-top. Great timing, as we shall see 92 degrees again today!

  5. Bubu

    Ok, feeling totally inspired now! And have to just say: that photo of you, and that outfit, is just hella-cute, absolutely love it! Also a big shout out for showing such a nice range of women in this post, the fact that it is so striking and positive makes me realize just how rare it is in the fashion world (though not on your site, thankfully).

  6. Stephanie

    I really love this post. I’m all about shorts. I love how much longer they make my legs look and sometimes I run into a wall when thinking of how to style them. This post really is beautiful. You did great.

    The dressy detail short, the short with a dressy blouse, the casual shorts with a blazer and the shorts with sassy details suit me best.

    I really would love to try the short suit, but I don’t own any blazers long enough to pull it off! Oh, well! 🙂

  7. Diana

    I am loving all the wider leg shorts options that are popular right now! For those of us with flabby upper thighs they are wonderful, comfy and flowy. The length is generally good too, not too short and not too long. I like a 5-6 inch inseam which is hard to find normally, but it’s perfect – not too short so they don’t ride up between the legs but still short enough to be hip (I have an irrational dislike of bermuda shorts!). I also like your classic cutoff jean shorts so long as they are not too snug in the thigh. I usually make my own by chopping the lower legs off of old jeans that have shrunken too short to wear as jeans.

    For me, shorts are a casual only thing, so I wear them on weekends and on vacation but never to work even though my work (lab) is very casual.

  8. joelle van dyne

    this collection of looks is AWESOME! i feel confident in shorts approx 1% of the time, but you’ve given me so many new ways to style them, i’m sure i can up that to maybe 20% or so, hehe. i really love your shorts w/ the cowboy boots, and the idea of pairing shorts with a long-ish blazer.

  9. Amy

    I love your website and read you daily. Thank you so much for showing ladies of all different sizes, shapes and colors in your shorts post–they all look fabulous–and so do you!

  10. Tabithia

    They are starting to come out with shorts that look like skirts, but don’t look like the skorts of the 90s. In fact, I have picked up a few thinking they’re skirts before and they’re just darling! They can give you the look of a casual mini skirt with the comfort of knowing they won’t show off your bum!

  11. Eleanorjane

    My theory on dressing involves accentuating the positive and minimising the negative. For that reason, I never wear anything above kneelength as I’ve got big knees and nasty bulges above my knees. (Don’t worry, I know I have many great features, it’s just that my upper arms and upper legs are not among them.)

    I love the style of the girl in the second picture down (dressy detail shorts) and I love her shorts, but I think they’d be more flattering just a few inches longer. If I had shapely legs, I would show them off like the girl in the last picture (shorts with sassy details) who looks so cute in a 1940’s pin-up sort of way.

    (Hope you don’t think I’m being disrespectful or hostile… just my opinion as a medium-large size person.)

  12. malevolent andrea

    Question, please, Sal. When you wear boots in the summer, are you barefoot inside them? Just the thought of socks+boots in the summer makes my feet sweat, but, OTOH, I think any of my boots would give me blisters without socks.

    • Sal

      Personally, I do socks. They add some cushion and a bit of absorbency! I have pretty thin socks, tho.

  13. Trystan (the CorpGoth)

    I lovelovelove all these photos! While ‘monochrome’ is prob. the only one I might wear from a personal taste pov, they all look fantastic & are flattering & stylish. Makes me want to wear shorts in public more — my problem seems to be finding flattering ones that fit which I *could* style like these photos, alas. More hunting, I guess, but at least I have better inspiration now.

  14. Lauren

    I live in a tropical country so I wear shorts ALL the time. I’m not very adventurous with my short choices though. I own a basic black pair and a cuffed denim pair, then go wild with my tops (usually long) and shoes from there. I’m a little afraid to try high-waisted shorts for fear that they’ll make my tummy or hips look too big. Maybe one of these days!

  15. The Waves

    I tend to have trouble with shorts; I like wearing them but can’t seem to make them work all that often. You picked very pretty ensembles; my personal favourites were the shorts suit and shorts with a dressy blouse.

  16. Nadine

    I never wear shorts (I’m a dress-wearing maniac), but Hoover DAM these are some fantastic outfits!

  17. Sonja

    Hi Sal,
    in your post you especially mentioned wearing shorts with boots, but in my opinion the shoes are so important in general! I bought a lot of shorts during the last three or four years and usually wore them in a very tomboy fashion with sneakers. But lately I’m exploring my feminine side and found a pump-like style of shoes with heels (by Camper, by the way) that I can walk in, and they are both oh so feminine and comfortable. Whereas the sneakers-look was more about just comfort and liberty of movement and actually made my legs look a bit stubby, my legs look slender and longer and those same shorts instantly look elegant and dressy with my heels on, independently from what kind of top I wear. I really recommend the combination!

  18. bravoerunway

    I love your ideas of ways to wear shorts aside from the typical t-shirt casual looks! I’ve yet to try shorts with boots but I may give it a go in mid September when it is cooler and I am trying to transition between seasons and pieces!

    I am definitely following this blog and look forward to your next post! Would you mind making an appearance at bravoe runway? 🙂

  19. sartoriography

    Thanks for the feature, lady! This is such a great post. I don’t often wear pants or shorts, but all this info and the photos make me rethink that whole plan. You even reminded me that I like one of my own shorts outfits! 🙂

  20. irina

    This is funny. I’ve found this web site in search for dressy shirts on the short girls, like myself. I love shirts and high boots and I always have been curvy and juicy type, known like this to my friends and being liked like this to my guy-friends too. Now I am loosing weight, though, for health, youthfulness and detoxing. Anyway, I found that heavier girls looks so much better in the shirts. I am a big fan of curves, still, and struggling in adjusting to my own-choosen sporty image in my head. Thanks for the posts though 😉