How To Pick Out An Outfit

In my previous post on my Outfits of the Week, I teased sharing my outfit picking out process in a future post, and ever since I have been brainstorming and paying close attention to when I pick out my outfits so I can best share my process here. In this post I will write about how I pick out my outfits each week as well as how I classify if I a like an outfit once it is picked out. I hope you enjoy reading and possibly even pick up a new tip.

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Step One:

The first thing I always do is pick out a piece to start off with, normally I have a specific piece in mind that I want to wear, but if not I will just choose something random from my closet and build my outfit off of that, In my opinion, this step is important because without it I have no jumping off point for the rest of my process to go. This piece can really be anything from a plain white tee to a pair of statement pants, it just needs to be something that I can build the rest of my outfit off of.

Example: Thrifted soft purple satin button up dress, I picked this because I love the fit and when looking through my closet, I noticed I haven’t worn it in a while due to its recognisability so I defiantly wanted to incorporate it into this outfit.

Dress: Thrifted

Step Two:

Now that I have this piece picked out my next step is to go through my closet and look for a piece of juxtaposition. For example if I choose a form fitting tight skirt, then I’m gonna want to match that with an oversized or more conservative top. When this step is replaced with a matching step (pairing with a piece that is the same fit/style as what is picked out first) I often notice that that is when outfits turn basic. This step can be utilised many ways, such as a more formal piece mixed with something more casual, it can be a drastically different material, the fit of the piece doesn’t always have to be what’s different, just something to juxtapose the first piece.

Example: Lately it has ben getting cold(ish) in SoCal, so I wanted to make this outfit more wearable by adding a cream thick turtleneck. This juxtaposes my dress (now skirt) because my skirt is more 90’s/ trendy style, whereas my turtleneck is more loose-fitting sophisticated piece. So they balance each other out it a way that feels seamlessly me.

Turtleneck: Vintage

Step Three

For step three it’s all about accessorising, now that you have a top and bottom its time to really make it your own. For me it depends on the look i’m going for as well as the colors of my outfit when picking out jewelry, I try to stick with only silvers or golds however mixing metals is never a bad idea when done right (like with rose gold and silver), I later want to do a whole post on jewelry (co-written with namer of this blog and sustainable jewerly maker Charlotte Brandman) on buying quality pieces and how to style them, but for now just keep in mind that you don’t want to overload it with jewelry, and having simple staple pieces is all that you really need. All my belts are not small enough to really hold in my pants, so I always wear belts as more of a structural device in my outfit to break up my top and bottom half in a cute way, but make sure that you are only wearing thick good quality belts, as a cheapy thin belt just makes your outfit look uber and unnecessarily trendy/childish. And last on accessorising is a jacket, and for someone obsessed with style, throwing on a sweatshirt and calling it good enough is never what I want to do. So I usually use my jacket as a form of structure, as a fit and flare silhouette is one that I commonly go for and adding structure to that is a must. I do this in the form of a trench coat or a oversized blazer.

Example: Because this turtleneck is thick and knit, I did not want to layer necklaces over it as there already was enough going on in my neck region. However I have the cutest pair of pick and purple/blue dangly earrings that pick up the soft purple in the skirt. I also just always wear my claddagh ring that was my aunts, my matching ring with my mom and my pink Tiffany & Co. heart bracelet.

Earrings: https://www.instagram.com/char.makes.jewlery/

Ring: Chelsea Market

Bracelet: https://www.tiffany.com/jewelry/bracelets/return-to-tiffany-bead-bracelet-GRP06688/

Step Four

Step four is shoes. Personally I'm not really a shoe obsessed person, so shoes are always my last step and just something to tie off the look. I normally am wearing a variation of the three shoes I mentioned in my 12 items post. Under the knee boots with a short skirt or dress, booties with a statement pant or more formal/ NYC chic girl look, and converse with a casual, schoolgirl outfit. In my opinion, converse are always a good default, however if you have Tabis in your budget then thats a different story.

Example: Because my turtleneck and skirt were pretty muted and classic, I wanted to further juxtapose those by wearing my black boots that I got from Forever 21 (before I was educated on fast fashion.) This way my outfit was a healthy mix of trendy and sleek as well as soft and classic, which is what I always go for.

Shoes: https://www.everlane.com/products/womens-day-boot-black?collection=womens-shoes

Step Five

Trying it on. I either hate or love trying on an outfit, I love it when it fits exactly like I hoped and looks like I wanted it to on me. And I hate it when it fits weird or just doesn’t work like I envisioned. Safe to say this step is kinda nerve-recking not going to lie.

But once I have the outfit on (or I’m silently judging someone else outfit) this is the criteria I have to decide if I like an outfit.

Is it too much? For me a simple outfit is always the most chic. I notice when I have on tights and a skirt and a collared shirt and a sweater and jewelry and boots I never really feel my best, however when I have on a simple classic top and bottom with minimal jewelry and nice shoes, that’s when my confidence comes through. For me a simple outfit represents a certain command over ones style, as they do not need to pile on layer after layer to put together an okay outfit, but a few pieces styled well will never go out fashion. I think an outfit is two much when it contains more than 2 or 3 prints, more than 2 severely contrasting textiles (fabric), or is just too layered.

Example: When I tried this outfit on I liked the little peak of skirt my sweater was allowing, I liked the fit of the clothes together, I liked the small detail of the dangly earrings, and the slight grunge twist that I got by adding the black boots.

So that is how I pick out an outfit! I hope you enjoyed reading and learned something about my process that you could possibly apply to yours, make sure to subscribe to my email list, the first email is going out next Sunday with my top beauty tip as well as some bonus and behind the scenes content about how this post was written.

Regan <3




Regan Mading

Regan Mading is a senior at the Orange County School of the Arts. She enjoys writing and social justice work. Her pieces have been published and featured in the New York Times,  LA Times High School Insider and Women In Politics Magazine. Her blog What She Really covers topics of fashion and feminism. In her free time Regan has been working on the perfect chocolate chip cookie recipe and cuddling up with Indiana, her attack dog.

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