20 Questions to Define Your Personal Style

The ultimate guide to figuring out what you actually like, not what your Instagram algorithm told you to like.

Feb 04, 2026

I’ve been known, at times, to be a trend-follower in both my style taste. I went through the peplum tops, blazers, and turquoise accent necklace phase of the late 00s. The twee indie sleaze hipster scene of the 10s that had me wearing ironic mustache jewelry, ballet flats, and American Apparel skater skirts. Then, of course, came the years of matte plum lipstick, giant top buns, and infinity scarves.

Just five or so years ago, I can remember saying vehemently, “I don’t care what’s in style, I’m NEVER giving up skinny jeans.” Now you wouldn’t catch me dead in a pair of them; my closet is full of wide leg and flare jeans.

As someone who has always been obsessed with and aware of design in all its iterations, I think this is natural. But over the years, there have been colors, textures, and motifs that have come back to me time and time again.

I loved millennial pink before it was even named millennial pink (and I still love it now that it’s passé – my office is painted that color, and it makes me smile every time I walk in the room). I will always be drawn to a chunky knit cardigan. I love anything with a retro feel, especially Mid-Century or 70s inspired. And I adore color and pattern – no one would ever mistake me for a minimalist.

These are the pillars of my personal style. And while I enjoy keeping up with trends, knowing these things about myself can help filter things through my own lens.

Most people approach personal style by looking outward – scrolling endlessly, saving inspiration, trying to recreate what looks good on someone else. But the colors you love, the textures that feel right, the way you naturally arrange things – these are deeply personal.

The good news? Your actual preferences have been with you for years. You just haven’t been systematically paying attention to them. So, let’s pay attention.

Below are twenty questions to help you untangle the patterns and preferences you already have. I promise you’ll learn something about yourself, whether you’ve had your personal style on lockdown since adolescence, or you change your aesthetic labels once a month.

Part 1: What You Already Own

Your current belongings are a goldmine of information about your actual style. Not what you think you should like – what you demonstrably do like.

1. Which five items in your home do you use or touch most often?

Think more aesthetically and less about utility. For me, when I grab a coffee cup in the morning, I always grab my Rifle Paper Co. mug with a gold handle and illustrated books. When I’m cold, I usually go for the fuzzy pink blanket as opposed to the many others in my house. I always go for one of two pairs of ruffled-edge socks I have from J.Crew, despite the numerous other socks I own. And I own a shocking amount of coats, but if the weather is cooperating, I always grab either my brown plaid teddy coat or my pink teddy coat. I just love them.

What are yours? List them out.

2. What do those five items have in common?

Now look at them together. Do they share colors? Textures? Materials? A mood?

Mine are all warm toned, cozy and soft, and a bit vintage-inspired. Whether I realized it or not, that’s my actual aesthetic showing up without me trying.

3. Which clothes do you wear until they’re threadbare?

Forget what’s hanging in your closet collecting dust. What do you actually wear on repeat?

I’ve gone through so many different versions of black knit turtlenecks. I wear them with stuff constantly in the fall and winter. It has to be a specific style and weight of knit to be flattering but still layer under skirts or dresses too.

I’m also very drawn to rib knit tees – I’ve purchased the same Marine Layer tee shirt in like five different colors now, and had to replace a couple already. I just love them.

What’s falling apart in your closet because you love it so much?

4. What’s the oldest item you still love and use?

Not the oldest thing you own – the oldest thing you genuinely still love.

I have so many cardigans in my closet, but the one I always reach for is an oversized, mustard yellow one that I got in the clearance section at Target in college. Nothing special, and worn to hell, but something about the hue and the chunky knit still calls to me after all these years.

Think about yours. Why do these items have staying power when others don’t?

5. Which items have you purchased multiple versions of?

This is a big one. When you love something so much you buy backups or similar versions, that’s your style speaking loudly.

I will always buy a knit sweater with a polo collar. I have probably a dozen variations on that style of shirt in my closet, because I just love them. I also have half a dozen pairs of black ankle boots that my husband swears are identical (they aren’t – some are chelsea boots and some are lugsoles and some are heeled).

What do you buy on repeat?

6. What’s in your cart right now that you haven’t pulled the trigger on?

Sometimes what we’re considering buying reveals as much as what we actually purchase. In the past few weeks, I’ve saved five different multi-colored striped sweaters to my wishlist. Three pairs of low-heeled mules. Half a dozen carmine red sweaters.

Check your cart, your saved items, your bookmarks. What patterns do you see?

7. What did you buy that you thought you’d love but never use?

The items you bought but don’t use are just as informative as the ones you love. They show you where your aspirational aesthetic diverges from your actual one.

Over the past couple years, I’ve purchased so many of those frilly little smocked crop top blouses – you know the ones, with the square neck, stretchy bodice, and puff sleeves? They always look so pretty online or in the store, but I NEVER end up wearing them. They’re always too short, a bit scratchy, and impossible to wear a regular bra with. Plus I never know what to style them with.

What purchases revealed a gap between what you thought you wanted and what actually fits?

Part 2: Your Visual History

Your childhood and teenage years hold huge clues about your authentic preferences – before you learned what you were “supposed” to like.

8. What was your favorite color as a kid? Do you still love it?

Mine was pastel pink, and guess what – it still is. Your childhood color preferences are often remarkably persistent.

9. What did your childhood bedroom look like?

My walls were pink and white striped (I was going for Parisian) and absolutely plastered with anything and everything I loved. Posters of boy bands, pages torn from magazines, dried flowers, framed art I found at a thrift store. If it made me feel something, it went up on the wall. (You can see photos here).

While I like to think that my styling skills have gotten a little (a lot) better since 2008, I still love a good gallery wall, and have a deep-seated need to customize any and every surface of any space I inhabit.

10. What stores or places made you feel something as a kid?

I have always loved a little curated gift store with candles and cards and cute accessories – lots of colors and textures, all impeccably styled together. Of course, I’ve always loved bookstores and libraries too. The hush, the smell of pages, the rush of finding a new story to get lost in. And I LOVED antique stores. (Yes, really, even as a child). The stacks of treasures waiting to be unearthed, everything a little chaotic and haphazard but brimming with potential.

Those places revealed what I respond to: maximalism, curated clutter, vintage touches, things that tell a story, warm lighting, and a plethora of colors and textures.

Even as a child, I hated anything stark or minimalist. I once famously told my mom that a room on some HGTV was “too white” and it freaked me out. I couldn’t explain why then, but it made me anxious and uncomfortable to think of existing in a space so undecorated and sleek. Now it makes perfect sense.

11. What did you collect?

Kids collect things they’re drawn to. Shells, stickers, books, rocks, postcards, whatever.

I collected old books, crystals or cool rocks, trinket dishes or small boxes, anything that felt special or like it had a story behind it.

12. What posters or pictures did you put on your walls as a teenager?

My wall art as a teenager always had to perfectly encapsulate exactly what I was into at that moment in time. I had posters for Pirates of the Caribbean, Twilight, Harry Potter, Vampire Diaries, Paramore, and Taylor Swift at varying times. I put up art class projects that I was proud of. Aspirational images of the life I wanted to live, clipped from magazines or printed from the internet.

13. Look at photos of yourself from 5, 10, 15 years ago. What visual elements are still present in your life?

I have always loved a good cardigan, some fun accessories (Claire’s hated to see me coming), a rotating selection of vintage-inspired purses (almost all leather or faux-leather), and some impractical but super cute shoes (ask me about the red polka dot Rocket Dog brand wedge heels I had in high school – would I wear them now? Hell no. But the principles are there).

The execution has gotten better as I’ve learned design principles and had more money, but the core preferences haven’t changed at all.

Part 3: Your Instinctive Reactions

These questions help you notice what you respond to in the moment, without overthinking.

14. When you walk into someone’s home and immediately feel comfortable, what specifically makes it feel that way?

Not just “it’s cozy” – what creates that coziness for you? For me: warm lighting (lamps, not overhead lights), full bookshelves, comfortable seating (nothing stiff or formal), plants, worn rugs, the smell of coffee or something cooking.

What makes a space feel like somewhere you could stay forever?

15. When you’re shopping and something catches your eye, what specifically caught it?

Train yourself to notice this. Was it the color? The texture? The shape? The weight? I’m always drawn to anything pink, brass, 70s inspired, or colorful. Start paying attention to what makes you stop and look.

16. What compliments do you get most often?

People notice when you’re wearing something that really suits you. What do they comment on? I notice that I get more compliments when I’m wearing something that I really feel like myself in – anything that’s colorful, or a bit fun.

17. What makes you feel most like yourself when you’re wearing it?

Not your fanciest outfit or your most expensive pieces. What makes you feel like you?

I have a few go-to’s – a plaid mini skirt, my gingham trousers from Sezane, the red acetate sunglasses I bought in London, a striped sweater with a polo collar, my fuzzy pink teddy coat, the round pink Bando crossbody purse that I hunted down on Poshmark after I spilled an entire latte in my first one on a plane (I also own the black version and I’m considering hunting down the red one – I love these things).

18. When you’re stressed or need comfort, what do you surround yourself with?

I put on a comfy sweater, grab a cozy blanket, make a cup of coffee in my favorite mug, and snuggle up in my vintage rust velvet armchair with a new book.

Your comfort choices reveal your truest preferences.

19. If you could only keep 10 items in your home (excluding furniture), what would they be?

This question forces prioritization. What do you genuinely love versus what’s just there?

Mine would include: my books (this counts as one, shut up), the rug in my living room, the vintage paint-by-numbers painting in my dining room, my vintage brass turtle magnifying glass, my record player, the antique Staffordshire dog statues I found for a steal, my brass library-style reading lamp, the brass hand-shaped curtain tie-backs in my office, the set of tarot cards I got in Salem, and the pink glass canister from my grandmother’s house.

Some patterns emerge – clearly, I love anything brass. I like vintage or vintage-inspired things. And I like things that tell a story or remind me of a trip or a memory. These are all great insights.

20. If no one would ever see it or know about it, would you still want it?

This is the ultimate test. Remove performance, Instagram, what anyone else thinks.

If you’re looking at an inspo photo, ask yourself – if you could have this exact aesthetic, this home, this wardrobe, this visual world, etc. but no one would photograph it or know about it, would you still want it?

If the answer is “yes, absolutely,” that’s your style. If the answer is “I’m not sure,” you’re probably borrowing someone else’s aesthetic.

What To Do With Your Answers

Now look at all your responses together. Print them out or write them in a journal if it helps you see them visually. Heck, gather up some of the items you mentioned in one spot if it’s feasible.

Look for patterns:

Which colors keep appearing?
Which textures or materials show up repeatedly?
What mood keeps coming through? (cozy, minimal, dramatic, playful, sophisticated?)
Are you drawn to bold or subtle? Warm or cool? Busy or calm? New or vintage?

You’re looking for consistency. The things that show up across multiple answers – across what you own, what you loved as a kid, what you’re drawn to now – those are your real preferences.

This is your style foundation. Not a borrowed aesthetic label. Not a Pinterest board. Your actual visual language that’s been with you all along.

Once you see these patterns, everything gets easier. Shopping becomes simpler because half the options don’t even tempt you anymore. Getting dressed becomes faster because you know what feels like you. Decorating becomes more confident because you’re making decisions from clarity, not confusion.

Ready to go deeper?

These 20 questions are a great start – they’ll help you see patterns you might not have noticed before. But there’s a more complete process for turning these observations into a fully articulated personal aesthetic.

That’s what we’re doing this month inside the Well-Designed Life. Over four weeks, we take you from “I’m noticing some patterns” to “I have a complete visual language documented in a reference guide I can use forever.”

We build your exact color palette (not just “I like green” but your specific bases, accents, and statements). We define your material preferences in detail. We help you understand your compositional style. And we create a written aesthetic manifesto that makes every future decision easier.

But February is just one month. The Well-Designed Life is a year-long curriculum that helps you design your entire life with this same intentionality – your work, your creativity, your space, your learning, all of it pulled together into something coherent.

This content is only available on my paid tier – but it’s only $6.50/month or $65/year. For less than the cost of an iced latte (with oat milk!) each month, you can get the full experience – bonus content, the full Well-Designed Life syllabus, and access to an ever-growing resource library of tools to help you build your dream life (coming soon!).