Black Friday Deals for Investment Dressing
Much to my surprise, this summer’s article about hiring a stylist to help me revamp my style is among my most-read and shared. My theory? It’s disorienting when you wake up one morning and feel like you don’t recognize your own body in perimenopause. Finding things that flatter can help you take back control and move forward with confidence.
I recently had a touch base with my stylist to talk about how to wear current trends without looking either too trendy or dated. And while we may not all be the same shape, there is a flattering fit for all of us. This week, I’m sharing an update about investment dressing (including my favorite wear-anywhere black dress), avoiding unnecessary purchases, and some pieces I’m eyeing for Black Friday to very intentionally fill gaps in my wardrobe.
Quick recap for new subscribers: After I started Phosis, I realized I didn’t have the wardrobe for the job. My years as a yoga teacher allowed me to perfect the athleisure look, but I didn’t have anything to wear for meetings with suppliers, beauty editors, and my team. After interviewing several women, I felt inspired by San Diego-based virtual stylist Connie Jesperson of The Art in the Find. She helped me zone in on three words to describe the modern classic style I’m going for — feminine, architectural, and elegant — and we went to work sourcing pieces that work for my lifestyle and proportions. We covered:
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Finding your color palette
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Favorite stores, among them Sezanne, which I’m particularly loving right now
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Shopping for your shape
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Tailoring to customize your clothes
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The importance of understanding your proportions
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Building a core wardrobe
Eighteen months later I’ve found the investment very much worth it. I’ve learned how to discern what trending shapes and colors will actually look good on me (and which ones to avoid), and that slowly investing in fewer, quality pieces that work together as a whole is more cost-effective than a closet full of less expensive items that don’t.
As it’s been over a year since we last met, I realized I had a couple of gaps in my winter wardrobe, so Connie and I reconvened for a Zoom call. Here’s a round-up of more of her wisdom:
Start With a Clean Slate
I relayed to Connie that I seem to keep reaching for certain pieces in my closet while others just hang there. I have a pair of slightly tapered black pants in particular that I now realize I’m not thrilled with. They fit well, and there’s nothing wrong with them, but I don’t reach for them. She dropped this advice: “It’s time to pass those pants along to someone who will love them just as much as you love other pieces in your closet.” (I prefer to donate items to my local Dress for Success.)
Questions as you’re considering what to keep and what to purge:
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Which pieces do you put on but then take off? Is it worth keeping these pieces?
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Do these pieces align with your lifestyle and what you want to do? Or would that piece serve someone else better?
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Are you hanging on to something that used to fit your pre-menopausal body but no longer suits your shape? Time to donate it.
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And finally, just because it’s cute on someone else does not mean it’s cute on you — especially if they have a different lifestyle than you do.
“Your clothes should be like your friendships — you can’t wait to see them, have a conversation with them, and be excited to wear them. What do your clothes bring to the table? Do they support you or do they drag you down?”
— Connie Jesperson, stylist and creator of The Art in the Find

My faux leather skirt doesn't look great with my eyelet blouse, even though I love both pieces. I love it with something that drapes close to the body.
Shop Your Closet
Instagram and TikTok will tell you that life isn’t worth living without a pair of over-the-knee boots, extreme wide-leg jeans, a barn jacket, and an oversized blazer this winter. Before adding a million things to your cart, Connie suggests styling what you already own in a new way. This sounds crazy, but I have tried on almost every top I own with every bottom, so I know which fabrics and cuts work together and which don’t. Yes, it took a lot of time. But it helped me understand how to pair items in my closet. I now know my fabulous faux leather skirt does not look great with the eyelet Sezanne blouse, even though I love both pieces. Rather it pairs better with something that drapes closer to the body. And the Sezanne blouse looks better with a pair of jeans.
Know Your Measurements + Proportions
When I used to buy things online based on what caught my eye, I could never figure out why I didn’t like them in person. Anyone else have this problem? Connie taught me to seek out each retailer’s measurement guide to ensure A) that the piece will work for me and B) that I order the correct size.
I’m petite so when buying jeans or pants, I now pay close attention to the details for rise and inseam, so I have a better idea of how it will fit on my frame. For example: high-waisted jeans are really high on my 5’2” frame, so not always a good choice.
Balance and proportion are also important. For example: Wide-leg leg jeans with a long oversized blazer will overwhelm a small frame, so it’s better for me to pair wide-leg pants with a cropped top, preferably one that fits closer to the body.
Need help figuring out what is the best length of pants for you? Check out Connie’s Insta post here. I promise it’s enlightening and fail-proof.
My Shopping List
My chat with Connie is helping me resist the urge to buy things just because they’re on sale or look fabulous on the model. Here’s my much more intentional Black Friday shopping list. (And no, I’m not getting a dime from any of the companies or products below.)

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Short Sweater Dress
The French are too fancy for Black Friday, apparently, so this short-but-not-too-short sweater dress I just bought is full price. I love it so much I recommend springing for it without a discount. J.Crew’s entire site is 50% off, so if I hadn’t already sprung for the Sezanne version I would have considered this one. -
Cocktail Party Flare
This black dress from Room 502 is hands down my favorite investment piece from my first session with Connie. I wear it constantly because you can dress it up or down or layer with different jackets and sweaters to make it seasonless. Right now it’s $100 off, so run, don't walk. I also just picked up this cream sweater with gold polka dots in case a holiday party comes up, but it’s sadly already sold out. -
Wide Leg Jeans
FRAME is one of those luxury denim brands that doesn’t really go on sale, so this is a great time to use Shopbop’s code (HOLIDAY) to get up to 25% off sitewide. This mid-to-high-rise pair sucks you in at the middle, but has enough give to be comfortable to wear all day. If you’re not petite or want regular denim instead of black I highly recommend this pair, which is 100% incredible but excluded from the sale. -
Cream Boots
I’ve been wanting a pair since spring, and Staud’s coveted Wally ankle style is 20% off with Shopbop’s code. They’re more of a want item than a need item, so admittedly I’m still thinking about this one. The knee-high style is on sale in tan suede if that’s more your speed. -
Fine-knit Turtleneck
I’m looking for ways to adapt my existing pieces for cooler weather, so I’m looking for a fine-knit turtleneck to layer under blazers and short-sleeve dresses with tights, so I can wear them with boots. Quince’s cashmere gets incredible reviews, and they have an array of offers that start tomorrow. Nordstrom has this version available at up to 40% off, depending on color and size.