Today we’re talking the ultimate comfort outfit: dresses and sneakers! I got a request on Instagram to cover this, and while I’ve posted related musings before in my Sneakers and Wide Leg Pants style notes, I think it’s still worth discussing specifically for dresses. I do love stompy boots or a sick pair of heels, but I’m always hoping that this combo becomes a complete non-issue because everyone’s feet can probably use some more love.
A lot of the tips here can be applied to any sort of less obviously casual jeans/leggings sort of outfit, but for scope I’m only going to use dresses in the examples. As usual, this isn’t meant as a laundry list of rules you MUST follow! but more as a a collection of details that you can consider when figuring out how you can adjust an outfit to fit your personal vision for it.
Additionally, you may have noticed that I don’t tend to wear a lot of “sneakerhead” type sneakers or streetwear style looks more generally, so I’m going to be covering outfit styling in a way that doesn’t center around making the shoe the star. if you’re already happily wearing your kicks any which way, then keep at it! But I know this is a combo that can be frustrating for people with less sneaker-centered wardrobes to fine-tune, so hopefully this is a good reference.
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So, how do you make your outfit feel intentional? I see two main approaches.
🧢 Keeping a similar enough levels of practicality and formality of all items. That is, going for more casual style dresses (as sneakers are casual active shoes), and/or dressier sneakers.
- Casual cut dress – less tailoring, more relaxed fit.
- Casual fabric – stretch knit fabrics like jersey/t-shirt material, athletic fabrics, or simpler or more rustic fabrics like linen or cotton poplin.
- More casual aesthetic – create an outfit in a style that is associated with a more free-spirited and eclectic look, such as boho, glam/rock/punk, or a more artsy vibe, vs an aesthetic associated with more traditional or formal/buttoned-up clothing like the internet’s favorite “dark/light academia” styles.
- More modern aesthetic – with dressier looks, sneakers will take less styling to look cohesive with more contemporary of futuristic styles as opposed to earlier vintage or historically inspired aesthetics. Think sneakers with an asymmetrical hem minimalist shift t-shirt dress vs a ren faire dress.
- Casual/sporty accessories and outerwear – Baseball caps, digital or smart watches, sleek backpacks, and the like. For example, leather jackets or denim jackets are classics for casual outerwear, although you’re certainly not limited to just those two options. I think these work particularly well with sneakers because they both have a more working/outdoorsy/active connotation historically than say, a cardigan, although all those options are certainly less casual than a suit jacket.
- Sneakers that are more occasion neutral and less tailored to a particular sport. So a more minimalist design of walking shoe versus one that plays up sporty details like springy soles or athletic fabric panels, or something that’s just more of a fashion sneaker i.e. flatform sneakers or sneakers with dressier embellishments (sometimes called “lifestyle sneakers” in stores)
You don’t need all of this at once – they can balance other elements out. For example, a short sleeved knee-length sheath dress in a thick matte stretch fabric will be more casual than the same silhouette of dress in lace or velvet. Or a waistless flared dress in a tinsel-touched baby blue woven fabric with lots of ruffle details will feel more casual than a tea length fitted bodice (more tailoring involved in construction) dress ending in a ruffle hem in the same fabric.
👩🏻🎨 The other way to approach building your outfit is including enough actively styled elements that the whole outfit comes off as something that must have been worn as an aesthetic choice and not as a combo of last resort.
- Color coordination through the dress and/or accessories. My go-to strategy!
- More obvious head styling, (and makeup, nails) – as I tend to repeat in every other post, very “done” looking head styling will have a halo effect on the rest of your outfit. There is of course the standard option of a “standard” polished look of light makeup and a trendy hairstyle, but anything that doesn’t happen on accident is “obvious head styling”. Someone with a buzz cut, blunt bangs, elaborate braids, piercings, bright makeup, or tattoos also has an intentional look.
- When it comes to looking at inspo photos on Instagram or Pinterest, stay mindful of the backgrounds making outfits seem more put-together as well. Think of any blogger wearing a black drop-waist dress and white sneakers looking impossibly cool in front of a backdrop of houseplants, a donut-shaped vase, and a couch with throw pillows featuring embroidered semi-abstract linework faces vs someone in the exact same outfit scurrying through the parking lot of a suburban strip mall to grab a part at the hardware store for their toilet which they realized has suddenly started leaking out of the base. You can’t take the background with you!
- More accessories/layers – aka the perennially recommended “third piece” (or fourth, or fifth). Going an extra step beyond the minimally required dress+shoes is an opportunity to show your outfit had some thought into it through a little more coordination or just some other fun fashiony pieces
- A general trendy look. i.e. a current it-sneaker (I’m not the one to ask about this as I’m not familiar with the latest streetwear and sneakerhead trends, but for example there was that year recently where those super chunky FILA dad sneakers were everywhere on Instagram) with a dress that includes some prominent trendy details, e.g. currently, puffy sleeves still going strong, or one-shoulder stuff seems to be coming back a la y2k for a sleeker look.
Now that we’ve got that reference tome out of the way, let’s take a look at some outfits! These are mostly on the fun-casual spectrum rather than strict bizcaz, but a note on that later.
Here’s a classic casual dress styling featuring white sneakers and white crew socks. It doesn’t have to be complicated! The dress, while pink and gathered, looks like a pretty casual fabric in a comfortable cut (dog walking appropriate, not any dry clean only party frock), so it doesn’t seem like an odd choice with sneakers on its own anyway, but the denim jacket further amps up the easy vibe+structure of the leather sneakers.
This one is a more accessorized summery look. The sneaker design includes a sporty stripe, but the pink coordinates with the dress and mirrors the pop of pink in the earrings. Here again the dress is a low-key fabric with a slightly rumpled breezy feel despite the more extra puffy layered puffy sleeves. The cat eye sunglasses work both to emphasize the outdoors element of sneakers as well as a fashion oriented shape. The purse, while not a utility bag, keeps the bright color scheme going while still feeling relatively sleek and utilitarian, similar to the sneakers!
Here’s an absolutely adorable example with a more formal dress. Monica’s cotton candy colored diaphonous poofy frock is paired with wavy hair and a statement headband, but the pastel lavender sneaker and baby pink sock combo continue the statement color scheme. I think that non-neutral color schemes can often work in favor of making outfits with less standard combos feel more intentional simply because the default for your average person would be something based on traditional neutrals.
This outfit features are more athletic style of sneaker. Gillian wears a relaxed-fit non-embellished black midi dress which works as a nice blank canvas sort of base, and a structured crossbody purse. I love that the purse has a bit of a sporty feel with the two-tone color and the clean streamlined cuts (curved edges, a bit of asymmetry), which feels cohesive with a sportier shoe while remaining in not literally athletic wear territory to make the whole thing read as a fashion look and not just a coming-home-from-the-gym-whatever outfit.
Okay, this one’s not a dress, but I wanted to up the variety of sneaker types and this photo collage from Adina caught my eye! Here the standout piece in the outfits is a boldly striped red and black skirt with a lot of interesting details. It can “hold its own” against sneakers with bold colors or heavy hardware or a chunky silhouette. It’s great when multiple statement pieces can feed off of each other’s energy. The tops keep with the stripe/colorblock/graphic loud feeling of the skirt but are a casual tees and sweatshirts, keeping the formality dimension of the outfit fairly uniform.
This outfit is a fun example on the glam side, accessorized wth with bright lipstick, a gold necklace, and an updo. The leopard print on the sneakers gives them a definitive fashion streak, and the dress too has extra styling details like the mock neck and asymmetric slit hem that add some interest.
And now here are a couple of recent looks including sneakers that I’ve worn!
In this strawberry-colored outfit, I’m wearing basic gray and white New Balances, so I usually prefer to keep those with an equally casual base outfit. I paired it with a sleeveless low-arm-hole textured cotton dress and a matching bralette, and then created more of a palette by color matching green accessories. Since the whole outfit was leaning more sporty, I went with a faded dad style baseball cap instead of the straw sun hat and a white but low profile digital watch (which also coordinates with the shoe color).
I think the matching socks do the most to help sell the sneakers as a coordinated item rather than an afterthought. If you’re working with a more chunky or athletic pair of sneakers, pairing them with crew socks in a coordinating color to the dress (match it to an accessory if you don’t like a matchy-matchy look from matching to the dress) is the easiest way to integrate them into a look. You’re gonna wear socks anyway! It’s also relatively easy to get a couple pairs of socks that complement your wardrobe colors.
Here was one that I styled for the post. These running sneakers don’t usually make it into my day outfits as I don’t typically gravitate towards sportier or streetwear looks, but I wanted to see if I had anything that still worked with them. I thought this tiered drop-waist eyelet dress actually worked pretty well, similar to the loose dress in Gillan’s outfit above. I think the same fabric with a similar level of ruffles in a fitted waist style would read more formal and feel less natural with a sneaker. A sleek backpack or a black/white colorblock canvas tote would be a good touch to tie everything together, but the best I got was the digital watch again for an additional pop of white (I guess the phone sorta helps there too). I don’t expect it reads that way to everyone, but the eyelet fabric reminds me of ventilated athletic fabrics and can read as vaguely sporty from a distance.
The next few are some variations on a puff sleeved quilted dress with white high-top Converse. The babydoll cut is both relaxed and more of a youthful look, which I think helps it blend with more casual shoes. I don’t think this one strictly needs any accessories to tie them together since both items are pretty minimal, but I enjoyed the subtle primary color scheme in this version with the blue padded headband and peek of yellow sock. I’d have liked a more visible sock ideally but I originally bought these ones to wear with my derby shoes and clogs.
One with outerwear! I like that while fleece fabric has an outdoorsy bend, the cut of this jacket is more of a fashion cut, which helps it feel cohesive with the more statement aspects of the dress. The large collar adds some structure into the loose and bulky silhouette. I know that for many people fleece is fleece and is unequivocally a camping vibe, but personally I also enjoy that in the teddy coat color fleece it has a slightly more luxe vibe reminiscent of fur, which works with the tudor/royal feeling from the deep red quilting.
And here’s the classic “white converse with a fancy dress” combo. Again, from my experience this is a love-it-or-hate-it combo, but I love it! People wear converse with everything up to prom and wedding dresses, but for casual looks i personally prefer pairing them with dresses with relaxed lines and matte fabrics like this because more structured or glam style dresses I’d prefer more of a polished styling and accessorized outfit, and I am lazy.
With an embroidered butterfly baseball hat to up the casual-romp-out vibe. Feels like a very Free People styling to me, as they mix statement flowy boho with somewhat grungy items frequently. I went with the burnt orange hat instead of the sage green one because I wanted it to lean more toward the “yeah it’s HERE let’s go do stuff” vibe. This combo certainly isn’t going to make your average fashion website’s “outfits every woman should have” lists, but it feels super mgetsdressed and I’m digging it.
If you’re in a place where you’re interested in adding more comfortable footwear options into your casual outfits that are more functional than floppy backless mules or less squeezy than heeled pointy boots, and are cool with more of a “lifestyle” sneaker, you’re in luck because there is a mind-boggling variety of options for more styled sneakers. You can find something that works in any aesthetic short of anything strictly formal. If you haven’t looked at the sneakers tab in your online shopping and aren’t sure where to look for some more fashion-oriented options, here are some fun shoes that I think would work for some different styles.
If you need a sneaker that reads more like a smarter shoe, hybrid oxford sneakers exist! I believe Cole Haan has the most extensive line of these, ranging from more decorated brogue looks to sleeker styles. These are not going to fool anyone into thinking they’re true dress shoes. They wouldn’t work in a strictly vintage aesthetic, but if your overall styling leans more contemporary and want something leaning menswear or preppy that could slide into a more business casual outfit, they’re worth a look.
If you’re looking for something sparkly and feminine for a more dressy outfit, Keds has a line where they’ve collaborated with Kate Spade to produce cute sneakers in a variety of silhouettes that would fit right into a glam, kawaii, or pastel style.
Besides Keds, a lot of brands will have gold or silver accented options, so don’t forget to filter or search for those metallic options in addition to your standard rainbow based colors.
These aren’t currently having a moment, but if you gravitate towards “hard” style shoes like combat boots, studded sneakers might be a fun option if you’re looking for a metallic touch (although be wary of ones with actually pointy studs, I assume those would suck every time they nip your ankle).
When it comes to colors, while it’s hard to go wrong with all-white, consider a sneaker with 2-3 colors that work with your closet’s common colors. Printed canvas or colorblock options often feel intrinsically more “here for fun and fashion” than going the other direction to the most low-profile pair you can find. For colorblock shoes that are a little less aggressively sports flavored with mesh panels and the like, an option is to look for shoes in a vintage sneaker inspired style. Both New Balance and Saucony have throwback lines.
It’s not super common, but even though it’s not my personal style, I’d love to see more neutral print animal sneakers for the fun touch but staying easy to color coordinate with many people’s wardrobes.
Speaking of Converse, while there of course is also the option of inserts, my recommendation is always to check if the style you want comes in the “Chuck 70” line, which is sturdier and has a little extra cushioning. The particular ones that i wear are the Chuck 70 high tops in “white/garnet/egret“
Especially as I’ve become more comfort-oriented over the past year and gone more towards dresses over separates, it’s been helpful to think about how I could make sneakers work in outfits without jeans or leggings. As someone with a decidedly casual personal style and work dress code, considering whether an item can be styled with more casual shoes has been something I weight more heavily. Since my personal aesthetic leans more romantic, that’s meant going for relaxed fit cuts and rustic fabrics like cotton gauze and embracing a more eclectic style (previously it was more important to me to stick with the vintage/fantasy academia inspired vibe and went for fitted bodices and structured fabrics). While I’m glad that through the old phase I became comfortable walking in heels when the occasion suits it, I love how becoming comfortable styling sneakers has given me more options to blend shoes that I originally bought for a more limited set of jeans-based looks.
How do sneakers fit into your wardrobe? Do you have any go-to accessory combos that you use when you want to dress up a pair of sneakers? Let me know in the comments below! Or feel free to leave a comment below on whether you found this post interesting or helpful, even if you don’t elaborate on it. I love feedback!
You might also like
- Style Notes: Socks
- Style Notes: sneakers with wide-leg pants and culottes (admittedly at this point I hate most of the outfits that I shared here, but I think the “notes on stuff I found searching Pinterest” section is still legit)
- Styling modest vintage-inspired pieces to feel less old-fashioned