Lifestyle-Based Outfit Planning (Part 2)

The More Boring Your Life, the More Boring Your Outfits. Or not?

Last week I assessed how I spend my time so I could identify which clothes I would wear the most frequently. Here are the categories I came up with:

• WFH – Comfortable & Casual: 70%. Working from home, school runs to an outdoor (very muddy!) school, and getting groceries.

• Business Meetings – Business Casual: 10%. Tech-related meetings, business events, and business travel.

• Meeting Friends & Family – Elevated Casual: 15%. Lunches, spending time with extended family, visiting friends, and running errands in more formal environments.

• Dinner / Theater / Events – Refined: 3%. Concerts, theater, evening events, and more festive dinners.

• Parties – Refined & Festive: 2%. Dancing-friendly, festive, sparkly outfits.

Dinner / Theater and Meeting Friends & Family have been the easiest categories to tackle so far and I covered them in my previous newsletter - and now I’m focusing on the rest.

Business Meetings – Business Casual: 10%

Business meetings are an easy category for me. They don’t happen very often - maybe twice a month - and I generally use one of my three favorite Tibi blazers for these occasions.

Left to right: Tibi Boiled Wool Fitted Blazer, Tibi Compact Stretch Fitted Blazer, Tibi Wool Slim Shirt Jacket (All sold out, but may reappear via Tibi.Fans).

In business meetings, I want to look effortless, stylish, sleek and professional. At the same time, I want to make sure that the outfit is not something that draws a lot of attention - it is in the background, and not the main player. I work in tech, so even a blazer can seem too conservative; I usually tone it down by wearing jeans. If I have something more formal - like meeting politicians or visiting an embassy - I’ll switch the jeans for wool pants, but I still usually rely on these three beloved blazers.

Outfit details (all old pieces): one of the 3 Tibi blazers, Flattered bag, Levi’s jeans, Cos ballerinas, Flattered loafers, Cuyana silk shirt, Uniqlo ring 3 T-shirt.

These outfits follow two main formulas:

• Interesting slim blazer + Levi’s 501s + T-shirt in various colors + relaxed bag for the business-as-usual meetings.

• Interesting slim blazer + wool pants + silk top + relaxed bag for more formal meetings.

How happy am I with my wardrobe in this category? I’d give it a 10/10. It’s easy, I love it, and I don’t use it often enough to get bored.

WFH – Comfortable & Casual: 70%.

This is my worst category - the “problem child” that really frustrates me. While working from home, I usually choose sweatpants for comfort - I hate wearing stiff jeans at home (though I never minded them when I worked in an office). The sweatpants need to be tapered (no wide-leg styles) because I bring my kids to a school that’s outdoorsy and often very muddy. I add a T-shirt and my beloved cashmere sweater from The Curated. Comfort-wise, these outfits are perfect, but style-wise…not so much. Also, I wake up while everyone else is sleeping, so there’s no time for a big try-on session.

All pieces are old: Tibi, Uniqlo and Arket sweatpants, The Curated sweaters.

In reality, I stick to one formula (at least for colder months):

• Sweatpants (simple or designed) + T-shirt + sweater. Yes, that simple.

How happy am I with my wardrobe in this category? I’d give it a 3/10. It’s comfortable, sure - but I want a combination that’s both comfortable and stylish, and I haven’t quite figured that out. My only idea so far is to explore casual skirts that I can wear while working from home, which would bring a level of refinement to the outfit - but I’ve yet to try it.

Parties – Refined & Festive: 2%.

My party outfits are troublesome because I have a lot of wishes for these outfits:

• No open arms or shoulders if I can avoid it.

• No dresses that ride up when I lift my arms.

• No mini skirts, mini dresses, or anything inconvenient for dancing or tricky when sitting.

• Nothing that overly accentuates my waist - I don’t want to worry about sucking in my stomach after a good dinner.

Surprisingly, I can’t think of many options that meet these requirements. I’m trying to find party dresses that check all these boxes, but I haven’t had much success so far. I was also quite uninspired when I tried looking in my wardrobe - only these two outfits were somewhat close to what I was looking for, and they are both black - a color I prefer to highly limit in my wardrobe.

All pieces old. Left: Tibi Elfie jean, off the shoulder top, Flattered shoes. Right: Lie Studio necklace, & Other Stories transparent top, Tibi Celia drape Stella pants, Tibi shoes.

How happy am I with my wardrobe in this category? I’d give it a 4/10. I simply don’t like it and haven’t found a suitable formula. The only reason my rating isn’t lower is that I rarely go out partying, so I don’t have to deal with this issue very often.

So the diagnosis and problem areas are clear, and I may look for different options to spice up my WFH and party life. For now, my plan is to let them marinate in the back of my head until I can figure out a good solution - let’s see how it goes!