10 Questions To Ask Yourself When Trying Things On

The topic for this post occurred to me as I was writing last week’s Try-On Haul. There are so many factors to consider when trying to decide whether to buy an article of clothing (or to keep or return, if you ordered online.)

I thought I would pull together a list of the things I ask myself when trying on clothes, in case this is something you need. In fact, I even decided to make a checklist for you to download, if you’d like!

First of all, you do have to try things on. And ideally, you should try on the item in question with a complete outfit you might wear with it.

That’s why I’m a huge proponent for ordering online and trying things on at home. That way, I can play around with various outfit combinations and be sure I really like the piece before committing to keeping it. Even when I shop in-store, I usually bring the items home and play around with them a bit before ripping the tags off.

I also highly recommend taking pictures of the potential outfits. Just a simple mirror selfie will do. For some reason, it’s a lot easier to tell if an item looks good or not from a picture than just looking in the mirror. Plus, I also like to have those pictures to help me remember the outfit combinations I liked. Then whenever I’m feeling stumped to get dressed, I can look back at those pictures for reminders and outfit inspiration.

Okay, so here’s a list of the questions I like to ask myself when debating whether or not to keep a certain item of clothing.

10 Questions To Ask Yourself When Trying Things On

#1. Does it fit correctly? (And does it fit my current body correctly?)

The most fundamental question you should ask yourself is whether the clothing item fits well. Pay attention to the shoulders, sleeves, waist, and inseam. Don’t be afraid to be picky. If you know you can do better, the item should go back.

If it’s an issue that is easy to tailor, be honest with yourself about whether or not you’re willing to go to the effort and expense to have that done. Some stores like Nordstrom offer alterations, so if you’re purchasing there, go ahead and deal with the tailor at the time of purchase. It’s too easy to procrastinate that task once you get it home.

Finally, avoid the temptation to buy something that’s too tight or too loose with the hope that it will magically fit someday. Let me let you in on a little secret: Someday almost never comes. Buy clothing that fits your body as it is right now.

#2. Does it complement your body type?

Understanding your body shape is key to dressing well. If you aren’t sure what your body type is, I highly recommend Kelly Snyder’s Adore Your Wardrobe Body Type Calculator or Jen Mackey-Mary’s Everyday Style School Body Shape Quiz. Both of those women offer paid courses, as well, if you really want a deep dive.

Ask yourself if the clothing item enhances your best features and flatters your unique body shape. Most of us are happiest in silhouettes that highlight our strengths and downplay any areas we’re less comfortable with.

Not to suggest that you should never wear a style you love even if it isn’t the best shape for your body, but in general, knowing what looks best on you will help make those decisions easier.

Sundry Stripe Henley (2) // MOTHER Pixie Dazzler (29) (option) (budget option) // VEJA Esplar (39)

#3. Does it work for your lifestyle?

Be honest about your lifestyle and daily activities. Is the item of clothing practical for your everyday life, and do you have somewhere to wear it?

So many times I am tempted to buy something, and I sadly put it back on the rack, thinking to myself, “I don’t live that life.”

There’s nothing more depressing than having a closet full of clothes for a life you don’t lead. Even if they fit and look great on, they won’t get worn, and you will feel terrible getting rid of them, so they will just sit there, creating guilt and visual clutter.

#4. Does it align with your personal style?

Your wardrobe should reflect your personality and style preferences. If you’re unsure about an item of clothing, perhaps it feels like a departure from your usual aesthetic. This is a time to ask more of these questions, and consider whether or not it’s worth the investment.

Sometimes, we need to take a risk to get out of a style rut, but if the item is too far outside of your personal style aesthetic, it may be hard to make outfits with it from your closet, and you may not find yourself reaching for it.

I like to compare most items I try on with my three personal style words: modern, polished, and understated. If I feel unsure about an item, chances are it doesn’t fit all three of those criteria.

similar jacket (S) // sweater (S) // MOTHER denim (29) // LOCI sneakers (39)

#5. Can you shop your closet and come up with two or three outfits with this item of clothing?

When considering a new item, I try to envision how it will fit into my existing wardrobe. Or better yet, I take it home and try it on with a few different outfit combinations.

If I can’t make a few complete outfits with it, I either purchase the pieces I need to complete the look, or I just return it.

#6. Is it versatile?

Consider the versatility of the clothing item. Can it be dressed up or down? Does it work for multiple occasions?

Versatile pieces will provide more value for your money. If it isn’t super versatile, but you still love it, maybe find a less expensive option. Always consider cost per wear when adding to your closet.

#7. Is it good quality?

Examine the quality of the fabric, stitching, and overall craftsmanship. Investing in well-made pieces may cost more upfront, but they tend to last longer and provide better value in the long run.

Again, consider the cost per wear, and don’t always be looking for a “bargain” or a “deal.” It’s generally worth it to pay for a quality item, especially if you plan to keep it for a few years and/or wear it often.

This is probably a good place to remind you not to purchase something you don’t love “just because it’s a good deal.” Shopping the clearance racks should be done very intentionally with a lot of discernment, because it’s too easy to fill your closet with a bunch of stuff that’s just so-so because “it was a good deal.”

If you wouldn’t pay full price for it, you probably don’t really love it enough to buy it on sale.

#8. Is it comfortable?

Style is important, but you shouldn’t need to sacrifice comfort to get the look you want. If an item is not comfortable in the fitting room, chances are it won’t be comfortable in your daily life.

If you aren’t sure, wear the item around the house for a couple of hours with the tags on. Sit, bend, stretch, do all the things you normally do… (except eat, of course; you don’t want it to get stained) but be sure it will be comfortable for your day-to-day life.

sweater (S) // denim skirt (29) // similar boots // belt (M) // necklaces (option) // earrings // Clare V. crossbody // similar sunglasses (option)

#9. Does it make you feel confident?

Clothing is a powerful thing. What we wear has a huge impact on our mood and self-perception, so only purchase items that boost your confidence and make you feel fantastic.

That might mean you have to kiss a few frogs before you find your prince, but it’s worth the time and effort to build a wardrobe you love that makes you feel good about yourself.

#10. Are you excited to put it on and wear it right now?

Sometimes we settle for things just because it’s a good deal or we’re too lazy to keep looking. But if you aren’t excited to put it on and wear it right now, chances are you won’t reach for it when you go to get dressed in the morning.

Avoid settling for “good enough” and carve out some time to find pieces that make you excited to get dressed in the morning.

Even if your time and/or budget is extremely limited, you deserve to have a closet full of clothes you love to wear. Hopefully this list of questions is helpful, as you are clothes shopping and making purchasing decisions this spring!

Okay, here is that checklist I promised you! Click here to download, or you can also save it to your phone.


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28 Responses

  1. Number 10 is my big deciding factor, as I’ve learned that if I’m not excited about an item, I’m probably not going to want to wear it. If I do wear it, it will be obligatory because I paid money for it.
    Some women might be making the mistake of wearing the wrong size. So they’re trying to decide if they like something enough to buy it, but not wearing the right size can skew the evaluation process. Maybe an important question to ask oneself is “Am I wearing the proper size?”. I see so many ladies online and in-person wearing clothes that don’t fit well. It’s usually jeans or pants that look one size too big.

    1. Great point! And just because something is trending doesn’t mean it’s flattering on everybody. I think now the women wearing clothes a size too big are trying too hard to fit into the current baggy pants trend, just like many women wore skinnies a size too small.

  2. Great post! Thank you!! I love that you echo one of my personal mottos- don’t buy it on sale if I don’t love it enough to pay full price. When I worked retail I was forever telling clients this. I think Bloomingdale’s is great for this when they do their buy more get more sales, etc. since their sale is current styles I’ve had my eye on and am getting a better price than I was willing to pay.
    PS is there still a website update coming? I’m on my third attempt to leave a comment without everything disappearing. Happy weekend!

  3. I love that you’ve comprised a list for us to keep… I saved it right away in my notes! I will say I take a lot more caution when making purchases based on these questions especially since reading your blog! I wish I had known many of these when I was in my 20’s and 30’s and made some purchases that really just ended up being a waste of money 🙈! Lessens learned! And it really does make a difference when getting dressed! I do number 5 a lot now when buying something new!!

  4. I love your list! I’m printing it right now to put in my wallet. For the last few years, I have been so frustrated with my closet. I would shop and have plenty of clothes, but always felt like I had nothing to wear. I also found myself having to declutter my closet too frequently. I would always donate the clothing to one of my favorite charities, but still felt guilty over spending money on things that had barely or never been worn. Then, something I read in your blog a month or two ago, helped me realize that the problem was my ratio of dressy clothes to casual clothes. It was all wrong. My lifestyle and activities have become much more casual over time, but I was still mostly shopping for the life I used to have. I would focus on buying clothes that were more appropriate for an office situation or dressy social occasions and not really invest any time, money, or effort into casual clothing. Once I realized this, I turned my focus to my casual clothes and began to level up in that area. By investing in stylish denim, elevated sweatshirts, and cool sneakers instead of silk blouses and dress pants, I can still have fun with style and actually have a functional wardrobe at the same time.

    Thanks again, and please do more posts like this in the future.

    1. Rhonda you said everything that fits me too. Since I retired it was hard to quit buying office clothes. Through this blog and other bloggers I am learning to buy for the life I lead.

      1. I asked my daughter to come over to help me build a more casual wardrobe and donate my office attire. It was difficult to let go

  5. Yes and for #6 under versatility, I try to always consider whether it’s good for multiple seasons. To me, those are “wardrobe stretchers”. Silk blouses would fall under that category for me, for example.

    1. Great point! And definitely worth taking your climate into account. I live in a hot humid area with six months of summer and only one or two months of a mild winter. I do buy heavy sweaters and winter coats, but since there will only be a handful of days I wear them, I don’t pay full price. But I’ve given myself permission to buy higher quality shorts since I can wear them for half the year. The same is probably true in reverse for ladies in colder areas.

  6. Great post! I echo the other comments left so far. #10 is a great one. If I don’t want to wear it right now, or even tomorrow, am I that excited about it. Another good one is the sale price vs. full price question. One question I ask myself, when purging clothes or even after buying and not wearing, would I buy this right now if I was shopping? If no, out it goes.

  7. This is great Jo-Lynne! To #8, I’d add that it’s a definite no if you will either have to fuss with it (constantly pull up the straps/neckline/etc) or sit/stand a certain way (it looks ok as long as you remember not to raise your arms, cross your legs while sitting, etc). As my mom always says, if it aggravates you in the dressing room, you won’t wear it!

  8. Your best tip for me is take pictures of yourself. It has been an eye opener for me
    Saved me many of those “what was I thinking?moments”

  9. #4 and #10 are my downfall. I see something that looks great on a model and order it, and it just doesn’t fit my aesthetic! I am petite and while I love bright bold patterns, they overpower me and make me self conscious. I would love to be one of those Lily Pulitzer wearing types, but I am simply not.

  10. Great list Jo-Lynne. I learn more the longer I’ve been shopping and I’m more selective. You helped me decide on the jeans I’ve been trying to decide on. I think I’d just feel like I stick out with the different lighter wash denim cuff on the ones I want to look good. I also struggle with……..my life style is casual and then when I need to dress for something or even dress little more for church, I struggle to have the right outfit for that. So, there has to be a balance when shopping. I prefer jeans and casual tops with sandals or booties or sneakers. I’m starting to buy more coats and completer piece jackets/blazers too. That helps to add interested to an outfit this time of year especially. Thanks for the great list…..its spot on.

  11. Thank you for this excellent list that I need now! I have finally realized that I feel the best when I am wearing my signature colors, so I no longer buy tops that are not in a good color for me. And I have started donating tops that aren’t one of my colors, no matter how much I like them. My closet does not need to be filled with a whole bunch of colors. I love everything about the light green trench cot you recently shared with us. But it does not fit my lifestyle or my personal style, so I will just enjoy seeing pictures of you wearing it.

    1. Yes Ginger……..since I let my hair go grey I’ve purged so many clothes in colors I just don’t feel good in anymore. It was hard, but now I’m finding new colors I enjoy wearing. More the colors I knew I should have been wearing all along. I just added some new pewter loafers and grey Sorel suede booties. I was needing shoes that went with my more cool tone clothing colors. I’m adding more upscale sweatshirts also, like Jo-Lynne shares.

  12. I love posts like this. That’s why your my favorite blogger because of you offer good advice about fashion . I’m working on #3. I do ask myself where am I going to wear this piece and how often. I’m working on #4. Often out of convenience I don’t always dress my personal style. I’m also working on #7. I am looking at quality and fabric content. #10 I do have some new spring pieces that I am waiting to wear but I know what you mean about it hanging in the closet a long time. In my case it’s because I buy things that don’t fit my lifestyle. I also think buying too many trends can be a mistake. I just got rid of puff sleeve blouses. Right now I’m trying to decide on whether the Treasure and Bonds brown plaid jacket would be wise for me to purchase. Since you wear it with jeans I am thinking I should buy it. Thanks for all you do.

  13. I would never buy another article of clothing (or leave the house) if I took pictures of myself in said articles of clothing.

  14. Great tips! My stylist friend always told me, if it doesn’t rank an 8/10 (scale of 1-10, 10=perfection) for you, don’t get it. I learned over time she was right. I used to allow 6s &7s by but never ended up wearing them much. Now if it’s not an 8, I don’t put it in my wardrobe. Knowing my most flattering colors also helps a lot. I don’t waste time or money on colors that don’t look good on me.

  15. Hi Jo-Lynne! This is the best post ever! Love the check list – I will buy something on sale only to wish that I didn’t- so then my “ catch and release “ game begins: return, return, return😁
    You are my new guru for style!

  16. Thank you the great tips! I took a pic with my phone and will go back to this list when I am out shopping again. Definitely need to quit buying so quickly and if it more thought for now on.

  17. Great set of questions. Especially the ‘does it fit my lifestyle’. I am a drawn to anything sparkly and tailored when my current lifestyle is anything but!

  18. This is a great list. Very helpful!
    It might be obvious, but a question I always ask is: Is the color flattering?
    That eliminates a lot of clothing that I wouldn’t end up wearing or enjoying.

  19. Great list! Honestly I feel like throwing almost everything in my closet in the trash and start over with items to fit this list.

  20. Thanks Jo Lynne – good reminders. I’m going to pass this along to my college age daughter (who tends to buy based on trends w/out asking more questions) 🙂

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