How To Dress Sporty Classic Style

How To Dress Sporty Classic Style

Bring that sporty vibe into your classic wardrobe.

How to dress sporty classic

You’ve seen this woman before. She has a casual style that still looks put together. She looks comfortable and chic, but she doesn’t look like she’s headed to the gym. She could wrangle kids or a volunteer committee. Her sporty outfit wardrobe is perfect for travel because it’s easy to wear, easy to move in, and still stylish. She’s usually busy, and her wardrobe can’t get in her way. Sporty doesn’t mean sloppy. 

If you’ve been following along with the classic closet style series, first we covered how to dress classic without looking dated. You can also read about Edgy Classic StyleMinimal Classic StyleCute Classic Style and Soft Classic Style.

I hope you read all of the versions because sometimes wearing the wrong details is as big as wearing the right details. If you’re not sure what your Classic Style Twist is, take the quiz to find out!


A sporty classic woman is on the go and needs her clothes to fit into that. She has a lot to do, whether she is a stay-at-home mom, an empty-nester, works in a casual environment, or volunteers with an organization she is passionate about, she has a busy life. She wants to be ready for anything but still look great. The key is not to confuse this with athleisure, which is far more casual (even though according to this article everything we wear is athleisure!). You don’t want to look like you would actually drop and give me 20 right now, but your wardrobe hints that you dug into your weekend hobby/sport wardrobe. Your keywords are practical and functional.

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CS Image Template

The hoodie style sweatshirt, the varsity stripes on the sleeves and the slip on sneakers are all sporty, and were perfect for a cool evening on the lake that day. The tailored fit of the sweatshirt and the colors kept it classic.

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If you want your outfit to say sporty, it’s the details that will tell the story. Look for details that hint at athletics, outdoor activities, and a slightly casual aesthetic. Just because you weren’t on the high school volleyball team doesn’t mean you can’t rock this casual-chic vibe. Sporty outfits could hint at basketball, hunting, gardening, boating, tennis, skiing, biking, golf, swimming, hiking, and anything that takes you outdoors. Everything suggests that you are active and don’t mind getting your hands dirty or working up a sweat when the time is right. That sounds like too much, doesn’t it? Keep reading. I’ll show you how to make it perfect for you.

Outerwear like utility jackets, utility vests, denim jackets, bomber jackets, leather jackets, denim vests, puffer jackets, hoodies, and puffer vests are an easy layer to throw on over a t-shirt, sweater, sweatshirt, or flannel to add a sporty vibe. The key with puffer vests and jackets is to get the super slim ones. Like, paper-thin. If it’s too puffy, you will feel suffocated. The key to keeping your layers chic and classic instead of frumpy is to make sure your layers are thin, have a tailored fit and some stretch when possible.

Hoodies don’t have to be frumpy and oversized. If you get them so they are fitted, they can be quite chic. And then you can even add a slim puffer vest or other layer on top without feeling smothered.

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CS Image Template

This is a sporty classic look I wore this spring when it SNOWED in late April. I tend to gravitate toward this look on my busiest days, when I have a lot to get done. I’m wearing a fitted hoodie, and the contrasting cuffs and waistband add a faux layered look and finished this sporty outfit look with minimal jewelry and slip-on sneakers. I kept it classic with my dark wash jeans that are stretchy and comfortable, the stripe pattern on my top, patent finish on my shoes, and bold color palette,  I was so comfortable this day, but felt very chic and put together. 

Hats like ball caps, trucker hats, baker boy caps, and beanies will save you on bad hair days or if you overslept. They will actually make you look more put together, which is the best kind of trick!

For pants your number one style will be jeans, but you might also like jogger style pants, cargo pants, leggings, and chinos. Honestly you can wear any pants as long as they have a little stretch. If you work in a dressier environment, even trousers and pencil skirts can have stretch to them.

Shirts can be t-shirts, golf shirts, button ups, sweatshirts, henleys, sweaters, pretty much anything as long as you get the details right. 

Details on clothes like thumb holes on sweatshirts, pockets, anything that hints at a letterman jacket or athletic uniform like sleeve stripes, numbers, raglan sleeves, or other graphics. Also rolling your sleeves or pushing them up suggests you are ready to get to work.

Try patterns like plaid, stripes, graphic tees, racing stripes, and camo (if you can find it in bold colors). Consider texture and textiles as well. If you love the water, fabrics that look like neoprene will hint at your inner mermaid. A lot of classic style clothes, like polo shirts, are now being made in technical fabrics.


Camo is a classic hunting pattern, and the utility jacket and boots add more sportiness to my outfit. The crossbody style of my bag is also ideal for Sporty Classic because it’s hands-free. The accessories are Edgy Classic, but you can combine any of the Twists!

The best fabrics will be chambray, denim, flannel, knit, t-shirt, cotton, and technical fabric. Natural fabrics that breathe like cotton, linen, wool, cashmere will keep you comfortable. Silk is probably too delicate for you. Stay away from dry clean only items. Anything that requires babying is too high maintenance for you. You want things that are comfortable, movable, breathable, and stretchy. You can even get finer fabrics with a little spandex added.

One of the key details to a sporty classic look is layers. Sporty people need to be able to shed layers because they get hot while doing their activity of choice, even if that’s walking to work. That can be achieved with outerwear, layering a button-up or sweater over a tee, or even a shirt tied around the waist, or a sweater around the shoulders for an apres tennis look.


This sporty outfit was perfect for a busy travel day. The down jacket is lightweight and packable, the hoodie added extra layering options (I wore a black tee underneath because I was traveling from snow to the beach).


The stretchy jeans are comfortable enough for a long international flight, sneakers meant comfort and style while rushing between connecting flights.


Simple accessories like studs or small hoops and delicate chains that won’t get in the way. Silicone watch bands or rings that you can wear while doing sports. Waterproof (looking) athletic watches, fitness watches and step counters infashion colors are functional and fashionable. Aviator and wayfarer style sunglasses are perfectly sporty, chic and classic. If you are outside a lot, investing in polarized sunglasses would be worth the money to protect your eyes.

Your purse is functional as a crossbody, backpack, or tote, but still stylish and chic in material and color. You’ll want something that leaves you hands-free, so skip the handbags. You can get nice leather bags, but avoid any material that needs to be babied, like lambskin. If the purse needs its own chair, it’s not for you. When considering sizes look for something that is big enough to fit your water bottle or small enough for just the basics. A cardholder wallet carries the essentials and will slip into the smallest bags.


The sneakers, utility jackets, tote and crossbody bags are all functional but stylish.


Your shoes should be able to take you on an adventure at a moment’s notice. They can be anything from boots to flats to sandals, but they have a substantial sole and non-slip tread. Nothing that requires a careful step or makes you walk like a baby gazelle, and they are probably very comfortable. Footwear like sneakers, boots, boat shoes, and moccasins are perfect. Sneakers can be cute and chic like slip ons, Converse, or stylish running shoes.

Fashion sneakers are a thing right now and come in all the colors. A recent study found that for the first time in over two decades the most popular types of shoes are “sports leisure,” which really means nothing to do with performance and everything to do with the look!

Continuing on with shoes, boots of every variety work, but especially duck boots, hiking boots, leather booties, and rain boots. Even flats and sandals can be sporty if they have a sneaker or non-slip sole. Something with good traction is important.


The tee and shorts are both stretchy but structured, the size of the bag is perfect, as is the crossbody style, and the sneakers are stylish but can take me anywhere. I added the Edgy Classic details I need to feel complete with the studs on my bag and the angular shapes in my earrings and tee.


Makeup is another way to keep it sporty. You probably prefer not to wear a lot of makeup because if you get active it could end up a melty mess on your face. To bring some definition to your face without feeling too made up, consider adopting the French makeup aesthetic: Brows, lashes, and a bold lip. Brows and lips frame the face and give just enough definition for a classic without being too much for your I-don’t-mind-getting-messy side. 

If you have light brows and lashes, and don’t want to risk raccoon eyes, try waterproof makeup like mascara, eyeliner and brow gel, or try dying or tinting them for a more natural look that still gives you the face-framing to enhance your features. If you want to wear a subtle smokey eye, then go for a light lip color. You might like this neutral eye makeup look as a quick and easy, everyday look. 

Neutral makeup look
A neutral makeup look keeps you polished without looking overdone in the heat or on a busy day.
This neutral makeup look goes perfectly with this sporty fair isle ski sweater, jeans and boots.


Hairstyles need to be out of your face, and even if they are high maintenance, they look effortless. Buns, ponytails, top knots, braids or pixies are all great options and suggest you just rolled out of bed and threw your hair up. You want to be able to keep your hair out of your face when you are active, so short enough to stay off your neck or long enough to tie back when necessary will be most comfortable. 

Instead of delicate nylons, try thick tights or layering with leggings, but remember: leggings aren’t pants. We aren’t going to yoga. Wearing them under a tunic or dress is a great dressed up sporty option.

Sports and Classic Brands

There are some brands that were made for you. Any of the athletic brands will be great for shoes like Adidas, Nike, Puma, and New Balance. Eddie Bauer, Columbia, Burberry, Lululemon, Athleta, Abercrombie, Converse, Sperry, G.H. Bass, American Eagle Outfitters, Born, Land’s End, Birkenstock, Tory (Burch) Sport, Chaps, Levi’s, Ralph Lauren, Polo, DKNY, Fossil, Patagonia, Frye, Lacoste, Hunter, L.L. Bean, Minnetonka, Ugg, Barbour, Under Armour, and Skechers. My favorite jeans are from Express because they are stretchy but hold their shape, flattering, and so comfortable. 


The classic is in the style and fit of the clothes. Classic includes button ups, dark wash tailored jeans (look for 2% spandex so they stretch for comfort, but hold their shape), stripes, chino shorts, flats, loafers, trench coats, and a very tailored fit. The overall look of the clothing is classic, and you sprinkle in some sporty details to add a hint of your active side. Your favorite striped Breton tee might be worn under a utility jacket. Your flats could have an athletic tread. You could wear a trench coat with jogger pants. You might enjoy more denim besides your pants. Make sure your flannels have a nice, tailored shape instead of sloppy oversized cuts (if it says boyfriend fit, it’s probably a no). Add some subtle accessories that suggest what you do to stay active. Have fun with layering, but don’t let it smother you.


Here is another sporty classic outfit I wore one wintry day last year. The sweater and jacket are reminiscent of skiwear, the aviator glasses are a favorite style among athletes, and the denim and boots complete the look. The tailored fit, the bold color palette, the stripes, the metallic silver, and the bold red lip are all classic.


I just listed a whole lot of options for adding sporty outfits to your wardrobe but don’t wear all of them at the same time. The trick is to pick and choose one or two sporty details. If you feel like you’re ready for the gym, you’ve gone too far with the sporty and you need more classic structure. You might be happiest getting your sporty details in your layers and accessories. 

Only you will know the perfect balance. Do you feel too dressed up in your clothes? Do you feel sloppy or underdressed? Is there too much athleisure in your outfit and you don’t feel like you got dressed for the day? Start with one sporty detail in your outfit and see if you want more. Some women feel better in more, and some can only take so much. It’s very personal. Also, don’t forget the bold hues and tailored fit. Those say you mean business.


I do sometimes get a little sporty classic in my wardrobe, as you saw above, so I love this particular style. I couldn’t find one specific blogger or celebrity who consistently sticks to this style and gets the colors right, but some you can check out who wear it are Merrick (though her color palette is very warm and brown-based. She also likes Edgy details as well) and Kelly in the City (she also does a lot of Cute Classic). I searched the interwebs to find a collection of outfits from various bloggers. 

Outfit #1:  The only thing I would change about her outfit to make it truly sporty classic is her shoes. Some sporty flats, slip on sneakers or booties would make this a perfect sporty outfit. That utility jacket has a nice, sleek fit, but is also functional. Also, I love that she’s not a 20-something could-be supermodel. She’s a stunning woman over 40 who looks perfectly at home in her style. This style isn’t reserved for college students. Her utilitarian bucket bag is structured and unfussy. Photo credit here.

Outfit #2: This outfit is heavy on the sporty with the vest, leggings, socks and rain boots, but with the stripes, chic black and white color combo, the very tailored fit, shiny hardware, and perfect manicure, it’s got plenty of classic. Her nails are also painted, but in a darker color that won’t show the dirt underneath if she gets her hands dirty. Notice that her sweater is long enough to cover her rear. Photo credit here.

Outfit #3: I love that she stuck to a crisp black and white color palette with her raglan baseball tee, jeans and sneakers, and added a bold red lip to it. A sleek black leather backpack or crossbody bag would be perfect with this. Photo credit here.

Outfit #4: Even dresses can be sporty classic. The denim shirt dress with the sneakers is a dressed up version of this style. Denim is sportier than a more delicate fabric. The cut of her cardigan lends toward Soft Classic if you want to add that undertone as well, but the layering is perfect for the Sporty look. The sneakers mean she’s ready to go anywhere. Photo credit here.

Outfit #5:  A nautical vibe is an easy way to get some Sporty Classic in your outfit. The striped sweater and boat shoes mixed with the denim and a baseball cap show she is ready for a crisp fall day on the lake or the dock, but this outfit would be appropriate for any casual day. The red jacket will keep out the wind and damp while adding a fall-appropriate dose of color. Photo credit here.

Outfit #6: The bomber jacket, baseball cap, jeans, and sneakers are all sporty, but the black color scheme, structured bag, shiny accessories and fit is all classic. Photo credit here

Outfit #7: The plaid on gingham, structured button-up and bag are pure classic, but the layered puffer vest, denim, crossbody style of the bag, and booties add a sporty vibe that says she could explore that trail over there. Photo credit here.

Outfit #8: This is how you take sporty classic to the office for casual Friday. A black blazer and trousers, a white tee paired with white athletic shoes and a chic, structured leather backpack take business casual to the next level. Her MLBB lip and natural makeup are perfect for the office or a casual day out, or for more drama add a red lip. In cooler weather, she could even layer a thin hoodie with the tee and blazer. Photo credit here.  

Outfit #9: Layer a sweater over a plaid flannel, add some sneakers, jeans and a tote, and this is perfect Sporty Classic weekend outfit. Make the jeans dark wash if you want a more dressed up look. Photo credit here.


As important as it is to add the sporty elements you want, it’s equally important to avoid certain elements if you want that sporty, active vibe. Studies have found that the way you dress shows who you are before you say or do anything. Your style is your biggest weapon in forming the first impression.

I’ve showcased Edgy Classic StyleMinimal Classic StyleCute Classic Style and Soft Classic Style. Learning about all of them will help you avoid the details that will take away from your sporty classic look.

In the Stunning Style Wardrobe Guide, everything is strictly classic, but in the shopping links, I provide as many style options as I can find.  You’ll find Edgy, Cute, Sporty and Soft options for many of the items so you can customize the wardrobe to your personal style and 100 outfit options for inspiration!!

Are you serious with a sporty side? How do you show that in your classic outfits?

Now that you know your Classic Style Twist, read about the different Twists to learn how to bring your own personality through while still embracing classic style.

Are You Ready To Create A Classic-Style Wardrobe That Makes You Feel Amazing?

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