Create a Personal Outfit Guide So You’re Always Ready For a Night Out
Don’t let “I don’t have anything to wear!” keep you from living life off the wall
As I look at the wardrobe I’ve built so far since reaching my weight loss goal, I’ve over-indexed on work clothes. I recently reached out to a group of girlfriends to organize a night out, and then panicked: What am I going to wear? And my closet didn’t say ish.
I need my closet to say “I got you, girl!” And I’ll share with you how I’m getting there so you can copy my swagger.
First, I unpacked the wallflower whys.
Before my weight loss, I never had much to wear for evenings out. I didn’t expect to be asked out on dates, I didn’t go out often in general, and when I did go out, I didn’t always look forward to it.
I don’t have to tell you that people living with obesity are socially isolated. You’ve either lived it or witnessed it, so I don’t need to drag out quantifying stats here.
Since using my wardrobe as a catalyst for self-discovery, I’ve found that saying the quiet parts out loud—specifically, acknowledging harms and limiting beliefs—helps me address and change them. Maybe you can relate to things I realized I’ve done:
Overdressing for work to try to offset weight bias. I’ve spent most of my wardrobe budget on work clothes, which didn’t leave much to spend on nights out clothes. (Facts: When it comes to stereotypes someone else holds, you can’t change what they believe. Only they can.)
Working overtime to distract from a painful or non-existent social life or from a toxic environment at home. Or believing that being a workaholic dispels the stereotype that people who have obesity are lazy. (More facts: That doesn’t work, either.)
Avoiding going out because it can be physically challenging. This is especially true in big cities where some restaurants are tiny. Booths and close tables don’t accommodate larger bodies, some bar stools feel like spin cycle seats, and then there are the people who stare or even say something about how difficult it is for you to just sit down. Some people in larger bodies have mobility issues that make it hard to go out.
So, my issue isn’t just that I need to add some pieces to my wardrobe. It’s also about being aware of beliefs that got in the way, and being intentional about crafting my social life. I’ve wanted more fun in my life for years! And having some outfits ready can enable that.
This isn’t to say that clothes can totally revive a social life. There are complex dynamics that impact people who have or have had obesity that can’t be fully addressed with a new wardrobe. And certainly, the fashion industry has been part of the problem. It can be helpful to work with a professional to unpack harmful internalized messaging and limiting beliefs.
Steps to personalize outfits for a social life
Putting together a mini-wardrobe for my social life seemed much harder than doing the same for work outfits. The day-to-night wear thing doesn’t put me in the fun mood I want to have when I’m out. And imagining what I need for events I haven’t even planned yet feels too speculative.
What’s working for me instead is looking at where I’ve been lately. Why the retro? I’m likely to attend similar events. Recreating outfits for the things I did last year seems a more specific and intentional way to plan ahead for nights and weekends. This could mean no more last-minute scrambling and no more unworn NWT clothes in my closet for a “someday” event that never happens.
So, I:
Opened my calendar
Made a list of last year’s social events
Grouped like events together
and recreated outfits for those events.
The outfits
Some of these outfits use pieces I already have in my closet (how about that!), and I used some pieces in more than one outfit. Even if I don’t buy the pieces to build out every outfit, I’ve got a clearer idea of how I want to show up when I go out.
A Missy Elliott concert and a Stevie Wonder concert
These very different (and tremendous!) artists have a common thread in their music: Afrofuturism. A colorful geometric wax print dress from Ghana fits, and it would also work for other concerts, too. This is from Yevu, a woman-owned and led company that pays its staff of mostly women above living wages. Women’s empowerment aligns with Missy’s feminist work, and social justice seems very Stevie. I actually had this dress in my closet when Missy came to Atlanta, but for an outfit redo, I’d do a better job accessorizing. I’d wear this with some white ankle boots and oversized bangle or cuff bracelets.
Yevu Smock Dress in Big Business, sizes XS to 4XL, $146
Soko Capped Quill Dangle Earrings in Gold Plated / White, $218
A Leslie Odom, Jr concert at the Atlanta Symphony
The venue and vibe make this concert different. The setting is more intimate and a little more dressy. Since Leslie Odom’s genres are jazz and crooning, I don’t think this outfit needs to be as formal as what I’d wear to a classical music performance. I’d wear flats because I love comfort, but heels would be lovely.
Dressed in Lala Mad About You Long Sleeve Mesh Dress in Forever Young Check, sizes XS to 3XL, $108
Vivaia Square-Toe V-Cut Flats (Margot 2.0) in Ruby Red, sizes 5-11 & widths A to EE, $97
Sunday brunch at an upscale restaurant with women entrepreneurs
I’d definitely like to redo the outfit I wore at this brunch. I wore a goal dress I’d had in my closet for years, a Hale Bob wrap. This was my first time wearing it out because it “finally fit!” Embarrassingly, it was too big up top and did not stay wrapped, despite all the fashion tape I’d used. Lesson learned the hard way about goal outfits.
I have a lightweight pastel yellow sweater, and one of my favorite brands has a couple of skirts that I think would pair nicely. The skirt has elastic in the back of the waistband.
Mango Pastel Yellow Fine Ribbed-Knit Sweater, sizes XS to XL, originally $50, presently on clearance.
Wolf & Badger Baby Blue Suede Square Buckle Belt, sizes S to XL, $69
Boden Isabella Cotton Sateen Skirt in sorbet pink or green and pink wide stripe, sizes 2 through 20/22, $135
Soko Capped Quill Dangle Earrings in Gold Plated / White, $218
Birthday party at a friend’s house, 60+ people
In my previous mindset (the wallflower “there are no cute clothes for big girls like me” type of thinking), casual meant clothes that covered my body and didn't look bad together.
Now, my perspective is shifting: Casual to me now means comfortable but definitely curated to express my personality. In this case, my outfit contributes to the party atmosphere and helps me introduce myself to people I don’t know.
I bought these metallic jeans recently to celebrate a milestone. They’re comfortable and fun. I’d pair these with two pieces I picked up in Mexico: a pair of hammered silver hoop earrings and a black leather bracelet with a silver plate.
Black crew neck cardigan: I bought this a few years ago from H&M, and a recent check shows only XS and S are in stock ($38). Universal Standard and other retailers sell similar sweaters.
GAP High Rise Vegan Leather Cheeky Straight Pants in silver metallic, sizes 24-35 in regular and petite, originally $98, presently on sale for $50.
Vivaia Mabel Square-Toe All-Day Standing Flats, sizes 5-11, $129. These are very similar to the shoes I wore (which are now out of stock). If you need a wide shoe, Vivaia has other styles in wide widths.
Girls’ night out
Twice last year I went to a ‘70s-themed speakeasy in Atlanta. Both times I wore cheap flare jeans that I bought in haste. They were too long, and the first time I ended up taping the hem at the last minute. I’d like to dress with more intention.
This outfit has a ‘70s vibe. Two notes: Platform shoes would have totally made this, but I love it when my feet are comfortable. I have the Vivaia Margot 2.0 flats in multiple colors. Large gold hoops with a necklace stack would be great with this outfit but I’ve had these Ivie Leopard Hoop Earrings on my wish list for a while. They’re by Symbols of Authority, a Black woman-owned jewelry company that uses ethical and sustainable practices. The jewelry designs incorporate culture and mythology and are meant to help women feel powerful.
WHBM fitted blue velvet blazer, thrifted from ThredUp.
Boden Polly Jersey Top, sizes up to 20/22, originally $60, presently on clearance. This print is out but there are other patterns. I’ve also seen this pattern on some thrifting sites.
Joe’s “The Molly” high rise flare jeans, sizes 23 to 34, originally $188, presently on sale for $132. I also spotted a pair of Frame mid-rise flare jeans on ThredUp for $60.
Vivaia Square-Toe V-Cut Flats (Margot 2.0) in Navy, sizes 5-11 & widths A to EE, $97
Exhibit at an art museum
I caught the Giants: Art from the Dean Collection of Swizz Beatz and Alicia Keys exhibit at Atlanta’s High Museum. Comfortable shoes are important, and the museum can be a little drafty. I want an outfit that’s comfortable and a little artsy. I actually like the outfit I wore; I’d stick with it.
Maeve by Anthropologie Kick Flare Cropped Pants, sizes up to XL, purchased on Poshmark, price varies (I paid $38)
Black crew neck cardigan. Again, I bought mine at H&M but similar sweaters are available from multiple retailers or thrifting sites.
Boden Durham Wool Blend Coat in Cherry Jam, sizes up to 20/22, $350.
Vivaia Mabel Square-Toe All-Day Standing Flats, sizes 5-11, $129.
The final touch: Confidence!
The Hale Bob wrap dress fail changed me. Now, if I’m trying something new—a mini skirt, wedges, metallic pants, a strapless bra—I’m going to wear it before the event, even if it’s just wearing it around the house for a few hours. Spending some time days before the main event gives me time to make adjustments, get comfortable, and go slay.
*Note: None of the links above are affiliate links.
I love these outfits AND I love the whole idea of outfit planning.
Love these outfits!