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75 Tips to Help Make Shopping for Clothes Enjoyable and Easier

April 11, 2019

It wasn’t until I ventured into style blogging that I became aware of how many women really do not enjoy shopping for clothes. I had just mistakenly assumed that all women either loved shopping for clothing, shoes and accessories or they at least enjoyed it somewhat. Silly me.

I get it. If I spend a day or even half a day shopping, I often return home with swollen feet, feeling sweaty and discombobulated, disheveled and a little discouraged. Fashion shopping isn’t for the fainthearted. And it’s not easy…for anyone.

75 Tips for Shopping for Clothes

But if we’re going to dress for our day we’re going to have to shop for our wardrobe. And I’d rather we be savvy, smart and successful shoppers than discouraged and defeated store hoppers. So today, based on the valid complaints I’m hearing from women on Facebook and around restaurant tables, I’m sharing with you 75 tips that can help make shopping for clothes more enjoyable and easier.

#1 – Approach shopping with a realistic and positive attitude.

#2 – Realize that no one can wear every thing. Some women probably look to you like they can easily slip into and look fantastic in every garment ever made. Not true. You have that in common with every other woman. They can’t wear everything. You can’t wear everything.

#3 – Understand that you will have to try clothes on to see how they look and fit. That, like flossing your teeth and scrubbing your toilet, is part of “adulting.”

#4 – Count on trying on more that doesn’t fit or flatter than does. If everything happens to work that day, great. You’ve hit the jackpot. But realistically, you’ll probably discard more than you purchase. (By the way, did you know that on average you have to try on 15 pairs of jeans before you can find one that fits correctly? Yep! It’s not just you!! We all have to try on a lot of jeans.)

#5 – Create and work a shopping strategy.

#6 – Set a reasonable budget for your lifestyle and plan to stick with it. If you don’t have a budget you’ll either over spend and later have regret or you’ll opt for cheap items when you could probably buy better quality for a more economical cost per wear.

#7 – Plan to build a wardrobe that works for you. Rather than just shopping willy nilly, do the foundational work I describe in this post about building a wardrobe that works for you.

#8 – Have a wardrobe essentials list for each season and stick with it. If you’re a subscriber to my blog, you have access to my fall/winter and spring/summer wardrobe essentials lists in the Freebies for Subscribers. And you can begin building a wardrobe essentials list for spring with the help of this post.

#9 – Know your style essence and shop for it...not your girlfriend’s style, your mother’s style or your 20-something-year-old daughter’s style. If you’re not sure what your unique style essence is, you might want to take my free and simple Style Essence Quiz and/or read this post, How to Dress for Your Personality.

#10 – Quit cramming new items in your overflowing closet. Streamline your wardrobe instead. It turns out one of the most prevalent reasons women dislike shopping is because it invokes feelings of guilt. They already have a closet full of clothes they’re not wearing, so they feel guilty stuffing new items into it. If that’s your story, start with this post, 10 Things to Take Out of Your Closet.

#11 – Get real about your lifestyle and shop for it…not the lifestyle you wish you had or the lifestyle you used to have. You can learn more about this here.

#12 – Narrow down the colors of your wardrobe and shop only those colors…ruthlessly. Most of my shopping regrets are results of straying from this advice. But when I heed it, I never have regrets. Read here to learn How to Choose the Colors of Your Wardrobe.

#13 – Use Pinterest effectively to strategize. Don’t just pin pictures willy nilly to your Pinterest boards. Organize your boards by seasons, types of clothing, etc. Then try to pin blog posts that actually include styling tips and shopping links.

#14 – Download the Pinterest app to your phone so you can pull up your pins when shopping.

#15 – Utilize style bloggers as resources. Follow bloggers who stretch you and that you just plum enjoy. But to help with a shopping strategy, make sure you’re following bloggers who share your body type, style essence and/or price points. Ask them questions, pay attention to their styling tips, notice where they shop and how.

#16 – Choose 3-5 stores to be your go-to stores for clothing and accessories.

#17 – Choose retailers where the clothing generally fits your lifestyle.

#18 – Choose stores where the clothing usually fits your body type and proportions. You can learn more about how to discover your body type and proportions in my style series, Dressed for My Day…My Way.

#19 – Choose retailers where the clothing is appropriate and flattering for your age. A lot of women are growing frustrated shopping because they’re pulling items off the same racks as their children or grandchildren. Not that you can’t ever shop the same stores. Of course you can. But be smart about it.

#20 – Choose retailers where the clothing generally falls within your budget. Of course, keep in mind that most retailers – but not all – have frequent sales where their clothing is marked down as much as 50% on a regular basis. So don’t rule out stores based on their full prices. That’s another reason why so many women avoid or dislike shopping. They’re shopping in stores where the clothing is lackluster when they could get similar prices during sales at higher end shops and department stores.

#21 – Cultivate relationships with the sales staff at your go-to stores. As someone who worked in a women’s clothing shop fairly recently, I know that these people truly want to help you have a good shopping experience. You don’t need to be afraid of them, annoyed with them or skeptical of them. Instead, get them on your team!

#22 – Enroll in the frequent buyer programs for your 3-5 go-to stores. (Generally, I don’t recommend enrolling in every frequent buyer program out there, just the places that are your go-to retailers.) If you stick to these 3-5 stores, you’ll accumulate points faster and reap more rewards, making shopping much more enjoyable and fruitful.

#23 – Subscribe to the email service for your go-to retailers. Not only will you receive sale notices, but you’ll probably receive styling guides and tips that help you shop better.

#24 – Follow your go-to stores on Pinterest.

#25 – Follow your go-to stores on Instagram. This past week I saw a styling video from White House Black Market on their Instagram story. So when I went into their brick and mortar store the next day I felt more prepared to shop there.

#26 – Follow your go-to stores on Facebook. Not only will you hear about flash sales here, but you can learn a lot about specific products if you read the comment feeds on their posts.

#27 – If appropriate for your budget and personal guidelines, get a store credit card at 1-3 of your go-to retailers. That way you’ll get even more benefits such as, potentially, free shipping, deeper discounts and special shopping days.

#28 – Go shopping with ample time and a can-do attitude.

#29 – Visit stores during the least busy shopping hours. Statistically, 6-8 p.m. on weekdays is when the least percentage of Americans are in retail stores.

#30 – Block out an ample amount of time to shop. Nothing is worse than feeling rushed when you need to make decisions.

#31 – Be prepared to try on clothing.

#32 – Wear some makeup and fix your hair pretty so you like what you see in the mirror.

#33 – Wear no jewelry. It gets in the way and I’ve lost earrings that way.

#34 – Wear the appropriate undies for what you’re shopping for. In general I’d suggest wearing a nude colored bra and silky nude panties. Nude so they don’t show through whatever. Silky so jeans slip over them easily. If you know you’ll be trying on sleeveless options or dresses, you might want to carry along shapewear and a strapless bra.

#35 – Carry in heels if you’re trying on dresses.

#36 – Take a comb to fix your hair if necessary.

#37 – Keep your attitude positive and your self-esteem in check. Remember #s 1-4.

#38 – Be picky about who goes shopping with you. If you have a friend or sister or mother or daughter (or husband) who genuinely loves you, has a positive attitude, has good style herself and will let you be you, take her. Leave everyone else home.

#39 – Ask the salesperson for assistance.

#40 – Ask the salesperson to bring you other sizes or colors. Use that call button on the wall of the fitting room.

#41 – Ask the salesperson for help selecting coordinating items. At least at boutique retailers like Talbots, Ann Taylor and Loft, they receive books with each shipment that explain how to coordinate the outfits. She or he should be able to help you mix and match items.

#42 – Ask the salesperson to help you select accessories, if needed, and try them on with the clothing. I take jewelry, scarves, handbags, etc. into fitting rooms with me.

#43 – When you look in the mirror, ask the right questions.

#44 – Ask yourself if the clothing fits well. Fit is king. Want to know how your clothing should fit? Check out this post, 9 Signs Your Clothes Don’t Fit.

#45 – Ask yourself if you like how you look in the clothing. Don’t just look at the clothing; look at your face. Does the clothing make your face shine or do you get swallowed up in or hidden behind the clothing?

#46 – Ask yourself if you can move and really live in the clothing. Sit down, walk around, bend over, reach up and around. Is it truly comfortable?

#47 – Ask yourself if anything about the clothing annoys you. Is there a tag that itches, a cuff that’s too tight, a seam that’s binding, a ruffle that looks funny, a weird little bump in a weird little place??

#48 – Ask yourself if you have at least 3 things to wear with the piece, either in your closet or in your purchases.

#49 – Use the 3-way mirror to check out all the views.

#50 – Take photos with your phone camera of every outfit or piece.

#51 – Take a breather.

#52 – Ask the salesperson to hold the items you’re considering. Then step away. You need a break. Another reason women loathe shopping is because, indeed, it is exhausting. It’s up to you to make it less so.

#53 – Take a break. Treat yourself to a coffee, soft drink or lunch. Or just get outside and sit for a while.

#54 – During your break or once you’re home, look over your photos. You may be surprised that your opinions change drastically from this vantage point.

#55 – Shop like an adult.

#56 – Shop for quality. You’re not a child who is going to outgrow your clothing. If it’s a wardrobe essential, you’re going to wear this for a long time. You don’t want to have to shop for this same item again this time next year. So make it a worthwhile purchase.

#57 – Shop for a good fit. You’re not a child who needs to grow into her clothing. You don’t have to “have a little growing room” in your pants. That growing room will just get you into trouble.

#58 – Shop for what makes you happy. You’re not a child who needs to please your mama or anyone else. Only purchase that which brings you joy.

#59 – When you get your purchases home, don’t remove tags immediately.

#60 – Try on your new purchases with other items in your closet. 

#61 – Save your receipts and packaging for at least one month.

#62 – Learn to shop effectively online.

#63 – Shop on a desktop or laptop computer, if possible. The websites are usually easier to navigate on a computer than they are on a phone or tablet.

#64 – Set up an account with any store you are shopping. That way you’ll have the ability to track your order more easily. You’ll also potentially be awarded coupon codes.

#65 – Use the online chat option if you have questions or concerns. I use these frequently.

#66 – Use the filter function when scanning the offerings. For instance, if you’re looking for jeans, use the filter to designate your size, the cut and color you prefer. That way you don’t have to look at all the jeans that don’t meet your specifications.

#67 – Shop stores online that offer free shipping. If they don’t offer free shipping, check to see if there is a minimum purchase that receives free shipping. Also, check to see if they offer free return shipping.

#68 – Shop stores online where you can return items to a brick and mortar store that is nearby. This is my preferred way to shop. I do whatever I can to get free shipping, then I take my returns to the store in Tucson. I get more selection than they have in the store this way, get to try the items on at home, but don’t have to pay for return shipping.

#69 – Order multiple sizes and colors of the items. If you are reasonably sure you will be returning something anyhow, why not order all you need to get a good fit? I’m generally able to get my extra items returned before they show up on my credit card bill. And since shipping is usually a set amount, the weight of your package is immaterial.

#70 – Walk away from your online cart. Usually, if you’ll walk away from your full online shopping cart, you’ll soon receive an email offering you either a discount or free shipping if you’ll come back and purchase your items.

#71 – Enjoy trying on your ordered items in the privacy of your home. But still, try them on with the right undergarments, a little makeup and the right shoes.

#72 – Try a shopping service like Trunk Club.

#73 – Utilize your personal stylist. She’s trained to help you shop for your lifestyle, body type, personal style essence and preferences. But she can also stretch you so you’ll try new things.

#74 – Set a budget for the service. Set a personal budget so that you only spend so much on each box or each month. But also set a budget for your stylist. Let her know how much you’re willing to spend on jeans, outerwear, accessories, etc. A shopping service doesn’t necessarily have to result in big ticket item purchases. It’s really up to you.

#75 – Refer friends to your shopping service. Bloggers aren’t the only ones who can refer friends to Trunk Club and other shopping services. You, too, can earn $50 toward your Trunk Club account with each referral who spends $50 on a trunk.

Look, you can follow all these tips and still find shopping for clothes to be less than enjoyable. But hopefully these suggestions have equipped you to make shopping a little easier and less painful. You don’t have to feel discouraged or defeated by it either. There’s a way to shop for your wardrobe…so you can dress for your day…beautifully!

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Blessed for My Day

When God gives us strength to overcome something, it isn’t so that we can shine, but so that He can shine through us. God strengthens us so we can withstand the pressure, get up the hill, put one foot in front of the other and close our eyes to rest. His strength doesn’t usually include a change of circumstances, but it often includes endurance, patience and surprising joy…in the face of those circumstances.

If you’ve been wondering when God will alleviate your trouble or remove that difficult person from your path, hmm, you might need to think differently. Instead, consider how He has already strengthened you in recent days to endure the hardship and be patient with the difficult people. That, dear friend, is the source of your joy!

May you be strengthened with all power, according to His glorious might, for all endurance and patience, with joy. ~ Colossians 1:11

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xoxo, Kay
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9 thoughts on “75 Tips to Help Make Shopping for Clothes Enjoyable and Easier

  1. Wow, Kay, this is an incredible list! Thank you for taking the time to walk us through these do’s and don’ts of shopping! I’m one of the shopping haters, LOL, so I’m especially thankful. Safe travels to you, dear friend. Enjoy a little break. 🙂

  2. I used to HATE shopping. But, in the past year I have lost 30 lbs through diet/exercise and have discovered some of these tips the hard way. This post would have really helped me if I had it when I started dieting! LOL. Before shopping, I like to window shop online and keep up with blogs like this one for ideas. Then, when I get to the store I can save time because I have a list to try right away. Of course not everything works, but I am in and out much quicker because I am a little prepared. When I am eyeing something, I try to wait for a sale and you do a great job of keeping us readers posted on those events. You talk about using the sales staff while shopping, I really need to do that more! Great tips, love this post!

  3. Super post! Since I’m newly retired, I have to keep in mind your suggestion of shopping for the life that I actually have. So for me, that includes mostly polished casual items with a few dressier things included. But now that I actually have time to shop, it’s not such a dreaded chore. Thanks to your encouraging words, I did order 5 pairs of white jeans via on-line shopping, finding the perfect one and sending the other 4 back. Have a few sweet days with your hubs!

  4. You do a wonderful and comprehensive approach to your blog which gives us all a great opportunity to learn and enjoy as well. I appreciate your hard work and your dedication to doing a good job. Thank you so much!!! I love your blogs, and the wonderful person you project through your work.

  5. Hi Kay,

    As someone who gets completely overwhelmed by clothes shopping (and therefore tries to completely avoid it until absolutely necessary), I love this post! I’m now due to go shop for a few wardrobe items for upcoming events, and I’m absolutely going to use your tips. So glad you shared them! ?