A Guide To Selecting Your Outfit Everyday

Today I want to give you steps to picking out an outfit for the day. I’ll give tips to elevate your daily outfit and pick looks that are your personal style and match what you’re doing each day.

Let’s talk about picking out an outfit. Your outfit choices can set the tone for your entire day, boosting your confidence and make you feel ready for anything.

In this post, I’ll dive into my process for picking an outfit everyday, and some tips to help you pick one as well so you feel excited to get dressed and confident in your choice.

4 Things I Think About Everyday When Picking Out An Outfit

1. What am I doing today??
   • This is the first thing I think about when getting dressed. If I’m working from home all day and then cooking dinner, I’ll choose something simple and comfortable for sitting at my desk all day, and working in the kitchen. Some days the comfy thing will be a dress, sometimes it’s leggings and a sweater, other times it’s soft wide leg pants and a lightweight blouse. If I’m going to be out and about during the day, that leads to my next question…
2. What’s the weather?
   • If you’ll be outside during the day, weather appropriate clothing is a must. Are the shoes you’re wearing appropriate for the weather? Will your clothing choices be cool enough or warm enough? Will you be going from hot to cold places and need a layer? If you take off the layer, will your outfit underneath be appropriate for the location and the temperature? Will you be outside all day and want to make sure to avoid something that could easily get sweat stains? These are all things to consider when choosing your outfit.
3. Start with one piece and build from there.
   • If I have a new item in my closet, I’ll often reach for that cause it feels new and exciting. This is a good place to start. I always start with the most statement piece first…like a colored pair of pants, or a statement blouse, or a dress. From there, it’s easy to add neutral pants and then finish with shoes.
   • If I’m starting with a top, I’ll pull it off the rack and set it out so it’s easy for me to pull pants or skirts out of my drawer and hold them up. If I’m wearing a layer, I’ll hang my shirt on the hook in my closet and put the layer over the top on the hanger so I can see how they’ll look layered together. I’m a visual person, so it’s easiest for me to hold things up together to see if they’ll work.
4. Don’t be afraid to try several variations before the right thing works!
   • I often choose a pair of shoes in my head while I’m putting together an outfit, but there are plenty of times that I put on the shoes and they look totally different than I expected. Don’t get frustrated…it happens to all of us! Instead, try something different. It usually helps for me to put two different shoes on and hold up one foot and then the other to see how they’ll look. I do the same with jewelry…hold up two earrings and see which one works! Don’t be afraid to put something back and try something else if the first choice isn’t working.

I asked you what your biggest struggles were, and these were your challenges. Hopefully I can give you some help with these!

• Going in and out of AC vs outside heat
  • My suggestion: If your workplace is super freezing, keep a couple of jackets or sweaters there. Choose ones that are neutral and go with lots of outfits. If you have several, you’ll always have something to wear and you can bring one home each week and wash, so they always get rotated.
  • Alternatively, if you’re just talking about going in and out of grocery stores or movie theaters that are cold, carry a jacket or sweater in your car and tie it around your waist while you’re out and about for an effortless feel but a backup layer.
• How to combine shapes – loose pants with tight shirts, etc.
  • My suggestion: read THIS POST all about outfit balance!
• Accessorizing – too much or too little
  • My Suggestion: I think two jewelry items is always a safe bet. I do earrings and bracelets, or a necklace and bracelets, or earrings and necklaces. I rarely do all three. I also rarely do statement rings, and my regular rings don’t count for me!
• Convincing self to get dressed when you stay home all day
  • My suggestion: give yourself a challenge and try getting dressed everyday for a month. If you notice a difference, keep doing it! If you decide at the end of the month that it wasn’t worth the effort, go back to what you’re doing. For me, I feel way more happy and productive and confident, and I’ve just created a habit of getting ready. That doesn’t always mean full makeup or hair, but it means putting on clean clothes and a little makeup, pulling my hair into a bun or brushing it, and that makes a big difference.
• Picking out shoes that balance the outfit
  • My suggestion: try on a few shoes! I often try on shoes, thinking they’ll work with an outfit, and then look in the mirror and hate it. Don’t be afraid to try a few and see what feels best. Also think about your activities for the day…does that shoe make sense with your agenda and the weather??
• Different combinations so it isn’t always the same (shorts and t-shirt)
  • My suggestion: Accessories! If you’re wearing the same kinds of basics, make an effort to add some accessories to your closet to add interest to your basics. Like a few hats, headbands, or hair clips, or embellished sandals or fun sneakers. Also add earrings or necklaces or bracelets to make it feel fun. And if you look in your closet and everything is plain and simple, think about adding a few better than basic tops to your closet this summer to mix things up.
• Take a good look to a great look
  • My suggestion: There are three things that take an outfit to the next level: hair/makeup, shoes, and jewelry. If my hair is a mess and I have no makeup, any outfit looks worse. A little makeup and my hair curled or pulled back in a sleek bun takes it up a notch instantly. Jewelry does the same for me…a statement earring, or a stack of bracelets or a few layered necklaces just add a little sparkle. And for shoes, a pair of nice sandals or cute sneakers are much better than a pair of rubber flip flops or a pair of athletic sneakers.
• What to wear when you’re having a tough body image day/bloated
  • My suggestion: We’ve all been there! This is when pieces with structure are your friend. Thin fabric that shows every lump and bump can make you feel more conscious of your areas you’re feeling bloated. A structured linen or twill or thicker jersey will smooth over your body and help you feel more confident. Also, put on some makeup and do your hair…things you can control! These always make me feel pretty and confident.
• Not enough time to think through an outfit for the day.
  • My suggestion: lay out your clothes the night before, or plan them out all at once for the entire week!
• Summer mom clothes that aren’t workout clothes but aren’t too dressy
  • My suggestion: look at this post with lots of outfit ideas for summer!
• Not feeling excited about getting dressed
  • My suggestion: If you’re bored of your closet, consider investing in a few new accessories (jewelry, shoes, hair accessories) that make it fun to wear your basics. If you only have basics in your closet, try adding some colorful pieces, like a bold colored top or dress or pants! Just make sure you can think of 3 ways you can wear that new item with things already in your closet, so you don’t get home with it and have nothing to pair with it.
• Looking cute without trying too hard
  • My suggestion: Add a classic piece to all your outfits! Instead of multiple trendy pieces put together (like colored pants and high tops and a graphic tee), try colored pants with classic sneakers and a white tee. The classic pieces keep your outfit feeling timeless and not overdone.
• Incorporating more FUN
  • My suggestion: add color and prints and embellishments to your closet! A pair of pearl embellished sandals, a bold red dress, a printed tee or blouse…they’re all ways to add more fun!
• Working in enough variety
  • I’m not sure if this means you’re not wearing what you have, or you don’t have enough to wear. But if you don’t wear what you have, try turning hangers backward after wearing (and washing) an item. This helps you easily see what you’ve worn and make sure you’re going through all your clothes before wearing a repeat!
• Not knowing attire etiquette for various activities
  • My suggestion: I create THE OUTFIT GUIDE for this specific purpose! It has outfit ideas by season and occasion. Also I have dozen and dozens of outfit ideas for other occasions, so if you google “merricksart what to wear to a high school reunion,” or my blog name with “what to wear to____” you’ll probably find outfit ideas! But if not, google “what to wear to ______” and there are often many many articles and ideas from around the web that will help you get dressed. The internet is your friend!!
• Colors that go together
  • My suggestion: The only way you can figure out if a color pairing doesn’t work for you is to try it! Don’t be scared to try different combinations. I’ve started a new series this year with color combinations to help you get out of your rut of neutral colors only…here’s “what to wear with olive green,” “what to wear with navy blue,” and “what to wear with blush pink.” More to come in this series!
• Finding looks that are truly comfy but still look put together
  • My suggestion: We live in a world where it’s all about comfort, and while I totally understand the desire to be comfortable, there has to be a little bit of give and take here. You can still have comfortable jeans, but they’ll never be TRULY as comfy as pajamas because it’s a different kind of material. That’s fine! Just find jeans that you like and make you feel great and are comfy, but it’s comparing apples to oranges if you’re comparing comfy denim to comfy pajamas. They’re just different. But there are so many dresses or pants or jumpsuits or tops out there that can make you feel very put together and very comfortable, but just accept the fact that you’ll feel a different kind of comfy to your pajamas.
• Feeling like I always look boring
  • My suggestion: add accessories! A little jewelry, a pair of embellished or interesting shoes, or maybe a hat or headband can take your look up a notch!
• Need it to be quick – no time to deliberate or change
  • My suggestion: choose your outfits ahead of time! If you know you’ll deliberate or want to change in the morning, take the weekend to try outfits for the week on, and then have them ready to go on Monday.
• Staying on trend but age appropriate
  • My suggestion: Mix classic pieces with trendy pieces! Can you still wear trendy sneakers at age 60? YES! But choose to pair them with a classic pair of dark wash jeans instead of distressed denim full of holes. Or you want to wear a trendy dress? Great! But add a structured blazer or denim jacket over the top and pair with classic flats or loafers to keep the outfit looking more elevated and less “teenager.”

I hope this is helpful!!

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