When your style is Classic, but your lifestyle is casual
How to balance Classic style and a casual lifestyle…
jeans | dress (similar) | skirt (similar) | pants
loafers (similar) | espadrilles (similar) | sneakers
A prior post about “style geography” generated a lively discussion in comments. Some of you mentioned that you either have moved or are in the process of relocating to a region where a more casual lifestyle (and style) predominates.
This article was published previously and has since been updated. I’ve left prior comments in place.
shirt (similar) | turtleneck | cardigan (similar) | shirt
jeans | dress (similar) | skirt (similar) | pants
loafers (similar) | espadrilles (similar) | sneakers
(I’ve created this basic capsule with a pared-back palette of navy, blue and white to provide a general idea of the types of pieces a Classic might wear in more casual settings. You can always adjust to your preferred colors.)
The elements of Classic casual style
“Classic” style by definition is elegant and understated. (Think Grace Kelly, Kate Middleton, Amal Clooney.) Because of the structured element it can read as more formal. So how can a Classic “casualize” their wardrobe without sacrificing their style essence?
✅ First, don’t forego structure. Classics NEED some structure in their clothing or they can look drab and tired. Structure doesn’t have to mean stiffness, though. Collared shirts, set-in sleeves, a front crease on trousers are all ways to add structure. Look for these details in your more casual clothing.
✅ Blazers and Chanel-esque tweed jackets can be dressed down (especially with jeans), and some sweater jackets may work well (avoid oversized, look for collared or structured styles).
✅ Yes, you can wear jeans. Look for neat fits (not super skinny) even washes, no distressing. Avoid extreme shapes like large flares. If you can, tuck your shirt in and add a belt. Woven trousers with a bit of stretch (again, not too skinny or relaxed) can dress up or down.
✅ Skirts and dresses can have a more relaxed fit, but shouldn’t be too soft or oversized. And avoid big ruffles, voluminous sleeves, gathered tiers, large or irregular prints.
✅ Stick to good quality natural fabrics as much as possible: cotton, linen, wool, fine knits. Nothing too fluid, flimsy, stiff, or bulky. Tee shirts are fine as long as fabric is substantial, not flimsy.
✅ Shoes: loafers, ankle and knee boots (in cooler months), ballet flats, espadrilles, classic sneakers can all work in a more casual setting. Remember to keep finishes smooth, and shoes well-maintained.
✅ Structured totes, shoulder or crossbody bags in smooth leather or canvas all work with casual outfits. Again, “well-maintained” is essential, be sure to repair or replace bags when they start to look too worn.
✅ Don’t forget the power of jewelry and accessories to dial up or down the formality of an outfit.
✅ Being well-groomed is important, but you may find you’ll want to wear less makeup in more casual environments. (And if you’re wearing your best colors, you’ll find you need less anyway. 😉)
Best brands to shop for Classic casual styles:
- J.Crew (many styles available to size 3X)
- Ann Taylor
- Talbot’s (many styles available in Petite, Plus, Plus Petite sizes)
- Vineyard Vines
- Boden
- kate spade New York
- MM LaFleur (for structured knits)
- L.K. Bennett
- Equipment (esp. their classic silk shirts)
- Me + Em
Have you recently relocated or made other lifestyle changes that have impacted your wardrobe?
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I’d love to see these posts for each of the style personalities. I was typed a starlet but I am having a hard time with what a starlet wears for casual wear.
You did a wonderful roundup of classic style suggestions.. All of these pieces could take you anywhere. Another blogger/ YouTuber broke down classic style into I think five different categories. The categories range from cute classic to edgy classic. Seeing the different ways classic style translates in each subcategory is interesting.
Do you have a link to the YouTube video? I’d be very interested to watch. Thank you!
Yes, her name is April of Stunning Style, I believe the post is called “What is your Classic Style Twist” https://stunningstyle.com/classic-style-types
For the most part I fit all of the style twists depending on activities. The primary one for me is minimal classic and the one I least identified with is the cute classic. On Pinterest there are quite a few examples of how classic style can translate.
Thank you for the link. I am apparently a cute classic, which explains a lot and makes so much sense. Once I saw her pictures of Resse Witherspoon, I knew I was “home.” Bows, polka dots, animal accents, bright colors: yep. I love minimal on other people, but for me, it always feels like it needs something more: color, fancy flats, or a cute brooch.
Thank you so much for the link. I am an Edgy Classic and a winter. First time ever I’ve found a style blogger
who shares these characteristics!
Susan, your posts on style taxonomy are always my favourites
Robyn. . .I’d love to see the blog post you mention here. Can you provide a link or blog address? Thanks!
I identify as a classic, currently wearing black bootleg jeans (as I have hips) and a black and white striped cashmere jumper. Would love to feel confident enough to tuck tops into trousers, with a belt but find for me, my hips and thighs ruin the look.
LOVE this post Susan! Now my 81-year young face needs something “edgy”in the form of new glasses.. Would you share where you found the frames you are wearing in London photos please.
Try Warby Parker. Lots to choose from and great customer service. If you don’t live near a Warby Parker, the online shopping option is easy to use.
Eyebobs is a brand I’ve been looking at. They have some unique shapes and brighter colors. I bought bright red frames in a small, quirky shape while in Paris, just before the pandemic. Finally got them fitted with my prescription last year and I love the way they add a big spark to even my simplest outfits.
I highly recommend MODO eyeglasses. I have received numerous compliments as they are stylish, lightweight, durable and good value for the mid-range price point. If your optician does not carry MODO, they can be ordered.
FYI: “Founded in 1990 with an international focus, New York-based eyewear label MODO has become synonymous with minimalist, on-trend designs. The label relies on innovative materials and high-tech manufacturing techniques to create frames that are built to last.”
Hi Kaarina, those frames are from Face à Face, purchased from my optician.
Thank you Susan!
Love your classic ideas! I didn’t know I leaned toward classic. I am going to a Southern California wedding in April. What would you suggest for a spring wedding? I am probably some sort of a summer, 5’7”, 160 lbs, 75 years old. I am very energetic and healthy.
I suggest a sleeveless sheath, shift, or A-line dress in a solid color. Fabric could be crepe or Ponte knit. Add a shrug sweater for summer if you like covering arms. Think Talbots.
Hi Julie, thanks! Regarding the wedding attire, it REALLY depends on where in Southern California you’ll be (near the coast it can be quite chilly, while inland it may be very warm), and the type of event it will be (formal? casual? outdoors?)
I’m currently bookmarking some Wedding Guest dresses, will have a post soon with ideas.
This is very much my jam stylewise. Dressing my meno pot has been a challenge as many pants have so much excess material in the hips and thighs that I look as if I could take off in a stiff breeze! Tucking in? If only.
Will keep this post for reference. Thank you, Susan
I have the same issue. I used to have an hourglass figure but thickened up in the midsection with menopause and am stymied about how to dress for it now.
IT has always been a struggle for me to dress down. I am a classic summer, of course. Thanks for the suggestions on this post. I will be keeping it for reference.
My favorite part of this post is your advice that wearing our best colors may require less makeup.
Thanks for this post. I’ve been following you for quite a while, way before you went to Red Leopard. After looking at their website I think I’m a classic gamine, if that’s such a thing. I’m short, 5”2’ and cannot wear big or flowy things. My brunette hair has turned silver and black looks better than ever on me, along with navy, red and cobalt blue. I find I need high contrast colors near my face like black/white or blue with b/w. I hope you show the gamine or classic gamine style soon. I know that gamine is your style too.
I clicked on the links to the retailers in your newsletter about Classic casual looks and was intrigued by the rental clothing program that L.K. Bennett has in the U.K. Have you come across any good rental programs in the US?
I’m intrigued by that too. Vince also has a rental program, but that’s the only one I’m aware of. I will be keeping an eye out for more of these in the future.
Thanks for letting me know Vince has a rental program. Hopefully more retailers will start offering rental programs!
I need to save this whole post! It’s very helpful to focus on why I feel comfortable in almost all of these suggestions. I’m wearing a sweater blazer with black jeans and a tucked in print blouse to a lunch meeting today. I changed out my necklace to one that is a little understated as it was leaning to too dressy. In my neck of the woods not being overdressed is a constant challenge as the mainstream outfit is torn jeans, an oversized sweatshirt or logger shirt, wool socks, Doc Martins and no jewelry. Several friends and I now have a Lunching Ladies date once a week so we can dress in nice clothes and fit in with each other.
What a wonderful idea, a great reason to ‘dress up’. Not sure what it says about society, when wearing clean, classic clothes can be considered’ dressed up’!
Great post!!! This hit the nail on the head for me.
Thanks for this post, full of good suggestions. I have been cast as a classic gamine. I get the classic part, but the gamine not so much. Your ideas here are helpful and what I am leaning towards–classic but mostly casually so. I wanted to note that Southern California has had a cold winter. If you are moving here or coming now, bring a down jacket or warmer coat. It’s not shorts and t-shirts right now.
If you’re interested in incorporating some Gamine into your style, you could try adding some whimsical touches, like a quirky (small) print on a blouse, or a quirky or animal-themed brooch.
Susan, a most helpful post! Thank you!
Tucking shirts in has been a big no for me in the last few retirement years but a good dose of bravery hit me this summer (New Zealand) Since tossing shorts/capri’s and instead wearing knee length pencil skirts, with some ‘ease’ in the fabric, very slightly blousing the tucked tops, I’ve felt both comfortable and confident. Now I just need to find some straight leg pants for the upcoming winter.
Brilliant post, thank you.
Try Trenery or Sportscraft as both labels do a range of straight leg trousers for winter.
Thank you, I’d forgotten about Sportscraft.
Thank you for these classics. Your skill at creating outfits that mix and match help me refresh my looks. I am still searching for a classic boyfriends blazer with structure and style. MWG
Retirement has changed the way I dress, more casual and less corporate. I’m trying to figure out ways to incorporate my work pieces into a casual wardrobe without looking uptight. Or maybe I need to get rid of some of that stuff and add new items. I’ve long thought of myself as a classic dresser but recently realized I’d been brainwashed by the John Molloy/Dress for Success nonsense and stuffy corporate dress codes into thinking that way. I’m probably more an Adventurer or Classic/Adventurer combo, or something that adds a more bohemian touch to Classic. I’m 64 and still trying to find the real me, LOL!
Really helpful post. Classic to soft classic dressing suits me. Your ideas for making classic clothing less stuffy – great suggestions. Thanks
Susan, I love this post! Do you know how the sizing on LK Bennett runs? I almost bought the cute navy top, but I am always between a S and a M and I saw that the buyer pays the cost of any return postage so I hate to guess wrong. I can only imagine how much that postage would cost.
I have some JCrew rewards to use up so am going to try out those pants!
No need to guess. Just call customer service and ask for the actual garment measurements. The chest measurement is usually all I need to determine my size. Actual numbers are so much better than their descriptions. There is a fine line between “slightly fitted” and “too tight.”
This is me. Even the lighter blues are me.
My mother was a classic and so am I.
I wish J Crew had a shop in Amsterdam… I love their style.
Greetje
I am going to the Amalfi coast in May. I’m 70+, short with large hips and dress casual. I am comfortable wearing a dress as opposed to pants. Any suggestions on what I should bring and where I can buy. Thank you.
The weather may be quite warm in in Italy in May. You might want to check out J.Jill for some relaxed dresses in linen and other natural fibers: https://bit.ly/3MM8QOl The offer many styles in Petite sizes.
Hi Susan: I LOVE these posts on style! I’m taking notes because I think Annie said that dramatics need structure too. And neat for gamines (I’m a dramatic gamine)– is that correct? I’d love it if you have ideas about where ‘dramatics’ could find clothing. I’ve been shopping mostly at JCrew and a bit at Talbots and Madewell. I’m not sure that these lines hit the ‘dramatic’ note! haha! I live in Northern California and I’m retired. I still buy some of Eileen Fisher’s pieces too.
Dramatics need both structure and angular details. I’ll keep an eye out for brands that would lean toward dramatic style.
Thank you so much! So far I’ve found nothing stateside.
Thank you so much for this post. I’ve learned about structured clothes from you and Annie but I confess that long standing habits clouded my understanding for a while! Because I’m older and have no waist (!) I’m modifying to tops that can be worn untucked.
I love these posts about personality styles! I’ve been buying from J crew and Talbots for decades—probably because I sensed I needed structure in my clothes (dramatic gamine). My personality isn’t really wanting attention but I get that I need color (vibrant autumn). So the drama is really in extremes I guess and I’m trying to channel Tulsa Swinton . Thanks for these capsules Susan!
I love this mini-capsule wardrobe and could see it working very well on a short trip. This is one of my favorite posts.
To echo Candice….. would love to see this for all the style personalities
I’ll be working on more like this soon. 😉