Tips For Successful Mom-Drobe Shopping (Cause It’s a Whole Lot Harder Now)


Dressingroom From time to time, we get reader questions that are focused on shopping – what to buy, where to shop, etc.  And unless I know you personally (or have some idea of your taste, body type and what’s in your current wardrobe), it’s a tough question to answer.

However, I realized that since having kids, my methods for shopping have changed drastically.  I tend to shop online (where I can google to my heart’s content while the kiddos are sleeping), and I tend to do better when buying all at once – meaning I shop once in the fall, maybe once in the winter, and once in the spring/summer.  Pre-kid, I was picking something here and there up almost constantly.  These days, I don’t have the time (or the budget).  And the few times I have tried to spontaneously shop post-baby (without doing my homework first)…the item typically ends up hanging in my closet, unworn.  UGH.  The WORST.  Money and time wasted.

So….here’s what I would recommend to mamas needing to shop.  I’ve tried to keep things easy, but this process takes some time.  Plan to give yourself a couple of weeks for the planning, shopping, final selection, just thinkin’ it over, and returning.

1.  Know ThySelf

Do you know your own style?  Do you know what you like?  This Mamas, is number one.  I don’t care what the trends are….know thyself first.  If you need some help determining your personal style, we came up with a quick and dirty method to determine your personal style last Spring.  Keep some of your fav style inspiration handy…just take a cell-phone picture or try sites like Pinterest (here’s a snapshot of my current pin board for Fall).

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Once you have a good understanding of what you like, take a quick look at what you need.  My method is simply this:

Pull on your most worn outfit – include everything: shoes, accessories, bag, etc.  Ask yourself:  What could make this more wearable?

That’s it.  You’re done.

Want more explanation on this point? Ok. While looking at your most well-worn outfit, try asking yourself some of these questions:

  • Does this outfit need to be warmer as the nights cool? YES?  Add an interesting cardigan (maybe nordic?  maybe cable knit?) or a cute hat to your list.
  • Do you find yourself wanting to wear this outfit more often, but something is in the laundry from over-use?  Maybe it’s time to get a few more.
  • Are you happy with the outfit, but bored?  YES?  Try switching out the boots and bag for something more current, add a of-the-moment scarf (see M’s tips on adding flare to basics for some rockin’ ideas).
  • Is the outfit just looking old?  YES?  Replace the denim/shorts/dress/whatever and add some new accessories.


That really is the core of this exercise:  Understand what you almost always wear….buy new things that make it better.  You’ll be happy with your closet and look great.  Success!

If you have more time, follow this same process with a few more outfits. Try on what you wear to the park, to brunch, to work, to date night, to playgroup, the outfits for lounging around the house.  How happy are you with these outfits?  What you “need” is partly defined by what you wear the most often and how happy you are with your existing outfit.

Be sure to write down your “needs”.

2. Establish Your Plan of Attack

‘Cause this is battle, people.  

We have so little time, once the kiddos come, that I strongly recommend you spend a few precious hours looking online before you start shopping.  Scope out your major retailers and see if they have anything that looks interesting to you.

Also scope out online catalogs and lookbooks, etc.

Come up with a reasonable budget.

3. Shop!

I strongly encourage shopping online.  It takes less of your time, and the selection is virtually unlimited.  Keep the following in mind:

  • Shop online at places that offer free shipping and free return shipping.  My favorite online retailers are:
  • All of these retailers will ship out a free return label.  Anything you don’t want put back in the box, slap on the return label, call UPS for a pick-up.  So. Stinkin’. Easy.
  • When in doubt, buy multiple sizes.  This can be scary.  Why?  Because hitting the submit button on a $2,000 order when all you want is a pair of jeans is scary.  So is your husband’s face when/if he sees the credit card statement.  But you need to order enough so you find the pair of jeans that makes you OVER-THE-MOON excited…instead of “these look OK….I wish they were a bit smaller/bigger/different color/whatever.”  It’s easy to get bogged down in returns when you buy and return in onesy, twosy fashion.  Buy big, return once.

If you’d rather shop in person….

  • Wear your favorite outfit, do you hair, wear makeup, get all spiffed up.  Bring your inspiration photos and a shopping list to help keep your focus.
  • Once in the dressing room, ALWAYS try on and ask yourself this:  Do you LOVE it?  Do you LOVE it more than you love your favorite outfit?  If the answer is no….proceed with caution.  (If you don’t love it while looking your best, you sure aren’t going to love it on mornings when you have dark circles and spit-up in your hair.)
  • Be prepared to leave empty handed.  (That’s what chocolate is for.)

4.  Try EVERYTHING on at home

boyfriend jeans how to shop Go through all purchases.  Try everything on with your existing favorites (your cutest jeans, shoes, etc.)

Why?  Because if you don’t like something while wearing your hottest jeans and high heels….you probably aren’t going to like it while wearing your slouchy boyfriend jeans and flats.

Start a return pile.

You now have a bunch of clothing you’d like to keep.  Go through again – are you SURE you’ll wear it?  Try them all on again with other well-worn pieces from your closet.  If a new item doesn’t easily go with the clothing you wear all of the time…it may not be as versitile as you hoped.

Be realistic.  One of my clients had the cutest preppy style, and so many of her outfits were DYING for a blazer.  And she loved blazers – she had a closet full of them.  The problem?  She found them too constricting to wear around the kiddos…which was, uh…most of the time.  It was time to give up on the blazer dream and go in another direction.  (We found sweater blazers and soft moto jackets instead).


5. Final Selection

If you’ve managed to find everything you were looking for and stay under budget, then you probably aren’t a woman.  Most of us are going to have to cull.  One of my favorite tricks is to check Ebay, especially for items like boots, bags, and accessories.  For example, I’ve needed a pair of cognac colored boots for a while….and just scored a pair of Veronica Slouch boots on Ebay for $90…saving myself at least $200.  (Little known fact: I rock at buying on Ebay.  Here are all of my Ebay Shopping Secrets.)

Lastly, check the price online – see if you can find your item cheaper somewhere else.  Also call the stores and ask when it’ll be on sale.

When in doubt, pair down to the nicest you can afford for something you’ll wear the most often.   That date night dress?  Unless you guys are hitting the town several nights a week….I’d probably move that to the bottom of the list, or at least look for something very budget friendly.

And please:  don’t settle for anything less than true love.  You want your heart to beat a little fast.  If you’re not thinking, “Yay!  This is perfect!!”, then return and keep looking.  Unless all of your clothing was lost in a fire, you won’t freeze to death while waiting to find that perfect sweater.  It’s always easy to get distracted by “new”…but if that’s the only thing that attracts you, the item is destined for the giveaway pile.  Focus in, laser-like, on only what you love.

Good luck!!





  1. This is genius! I just went jeans shopping on Friday and I wish I would have read this. It makes perfect sense. I guess I need to do some thinkin’ before I head out again…
    Oh and I totally laughed at the $2,000 order, ya, that would not go over well around here. I think I would be doing some serious couch time if I did that without some explaining before I clicked submit. 😉

  2. Thanks for these AWESOME tips. I do not have the energy to try on all my outfits, but it is pretty simple…levis or lee and black or grey fitted tshirt is my FAV. Add scarf or jewelry or jacket or cardi and change up the look so easily. I get birthday moolah in Nov and plan to buy Gap tshirts and just accept this is what I do. I also plan to get some nice dress pants tailored now that I am slimming down, ditto two boxy linen jackets I have that I think would be better fitted…glad to have teh free shipping and return links. YEAH!

  3. You’ve got to be kidding me. You shop three times a year? Are you going through a growth spurt too? Instead of being trend obsessed, you can save time and money by picking out classic pieces and replace them when they wear out instead of when the go out of fashion.

  4. I found this helpful as I reorganized my closet and thought about a few new pieces that would be helpful (AGAIN).
    It feels like the 2 years of pregnancy and then postpartum have required closet reorganization and strategic shopping every 3 months…actually, I think a blog piece about how to approach closet organization/clothes storage/shopping for that 2 year period would be super helpful. You know, like it would’ve been helpful to know that I would need 5-6 storage containers through which I could cycle (1) early pregnancy (2) mid-late pregnancy (3) immediate postpartum (4) nursing with post-partum body (5) nursing with back-to-normal-ish body but big boobs and (6) weaned and back-to-normal-ish body…and some discussion of how to strategize that whole process. I mean, some of the stages overlap to some extent (e.g. early pregnancy and immediate postpartum). Sigh. Especially since, having now finally arrived at stage (6), we’re now about to start TTC again!

  5. Excellent advice! I agree that if you go shopping in person, dress for the occasion. Not just for the reason you stated, but for added confidence. You won’t be so likely to let the bossy salesperson intimidate you into buying something you don’t truly love if you are dressed up. It gives you (or me, at least) confidence.

  6. Casey, I’m really surprised by the snarkiness of your comment. We’re a group of nice, supportive moms, and comments like these don’t jive with our community. Yes, I’d say starting at less than a hundred pounds, popping up 40 lbs during pregnancy, down again and everything in between (including all the permanent changes many women’s bodies undergo throughout the child bearing process) TWICE over the past 4 years, would qualify as a “growth spurt,” or in most cases, worse.

  7. great article. the idea of shopping just three times a year for what you’ll need for that season is SOO much easier than what i have been doing … trying to cram it in at whatever store i’m at when the littles seem like they’ll be in a good mood for awhile and will hang out in front of the dressing room mirror with me. 🙂 my body has been changing like crazy throughout the journey of pregnancy/postpartum/nursing/trying to get back to “normal” (really, a new normal) and things that used to work last year or even last season just don’t work anymore. thanks for the tips on the websites with free return shipping! that just saved me big bucks. 🙂 luv the blog and keep up the good work!

  8. THANK YOU for such a great post! It is so spot on and popped up at the perfect time. Now, I have a question – what do you do when you don’t have a favorite outfit?? Well, I have an outfit I wear all the time, but it consists of yoga pants and a t-shirt. And, it is far from pretty on me 😉
    I think I might be able to shed light on Casey’s comment. For I know I will be shopping several times this year and in future years as well.
    I am a mom whose kiddos are older – 5 and 7. I went through all sorts of body stuff in terms of doing round after round of IVF/pregnancy/nursing and then repeating it all over again. My body has been all over the map – literally with things shifting, growing, shrinking (who knew I could go from a C cup to AA?!). My boys both had a lot medical issues and my life was just chaotic and filled with trying to keep them healthy, out of the hospital and juggling appointments. I purged a ton out of my closet and lived in whatever worked in the moment.
    Thankfully they are now happy and healthier than ever. They are both in school, and I am ready to regain my style. I know from reading the blog posts, and from living my life, that I will be a lot happier and feel a lot better when I am able to look in the mirror and see my fashionable self smiling back. It is time to reclaim “me”…
    That being said – there is not much in my closet. So, I will be shopping over the year to rebuild a wardrobe that represents the basics, but also reflects who I am and the new body I am embracing post kiddos. That will take time…Thankfully I am at a stage in life where I will have the time to do so.
    Thanks for all you do! I love this blog – if only you guys lived in Boston!

  9. Thanks for the comments, Gang. Glad to know this helped! Shopping (and spending $$) can be tough, post-baby.
    @RS – I have no storage / organization tips for you. I tend to purge things from my closet as my body changes, and I just shove everything into a garbage bag…only to be raided at uneven intervals and shoved back in. M and I have often laughed about what feels like the VAST amount of clothing we’ve amassed in the last four years. Especially considering that we both once had work wardrobes in addition to all of our transition wear. Wow. It sounds, however, like you DO have a system. Wanna guest post? 🙂
    @NoDramaMama – GREAT point. Especially when trends have shifted (as they have done in the last few years)….it’s intimidating to stare at a rack full of stuff thinking WTF? Those salesgirls can smell an easy kill a mile away. 🙂
    @Beth – You are right on – it will take time. Because the styles have changed SO much in the last 5 years, I’d take it slow. To be honest, if you are a daily yoga pant wearer….maybe just up that uniform a notch. Pick out a cashmere sweater, scarf and flats that go with your yoga pants, or a really cool workout jacket (try Stella McCartney for Adidas or Lululemon, etc). Or swap out your yoga pants and tee for cute jeans and a drapier, more stylish tee. That gives you some options while you are figuring out your style. I’d go outfit by outfit, though. Make sure you have a complete outfit – one that includes the shoes, bag, accessories. It won’t help if you get a bunch of cute tops and jeans, but don’t have the shoes (or boots) to go with them. Does that help? (And I’ve heard Boston is amazing. )

  10. Awesome post! I live in Germany and while I can find great things here, the euro to dollar exchange rate still dictates that I make make most of my big purchases online with US stores… and now, thanks to your article, I feel totally justified doing the “buy and return” game!! 🙂

  11. What a great post!! 🙂 Great tips, and I’m going to give them a try. My biggest downfall is the clearance purchases… I grab things that are okay because they are cheap, whether online or in a mad dash through the store with kiddos in tow. Then when I have time to try them on and think about it, I realize I don’t love them, but don’t bother to take them back because it’s not worth the trip or return shipping for such a low-cost item (or, uh, the “final clearance-no returns” dilemma). The result? I have drawers and hangers full of almost-new clothes that I don’t really want to wear. I need to plan my purchases more carefully and buy fewer things that I really love. I think I end up actually spending more money clearance rack shopping, since I keep constantly shopping because I feel dissatisfied with all that’s hanging in my closet, despite it being new!

  12. Loved this post!!!!! I had never thought about the outfit I wear most being the base to help me figure out what I need to buy. Thanks to your post on personal style and now this one I am all set for fall/winter. Love your blog Thanks.

  13. Shana – Thanks for the advice – it makes perfect sense. I wouldn’t have thought to do one outfit at a time, but now that is the plan. I do think that I will go with some skinny jeans (lord help me!)and drapier tops so I am able to break the yoga pant theme. Love my Lululemon’s but I need a change. I’m still so intimidated by making the wrong choice, not liking clothes on my body, or not finding things I LOVE. However, your post gives me a plan of attack!
    And, I live exactly halfway between Boston and Providence, RI – it is perfect!

  14. I sort of have the opisopte problem…I get rid of clothes all the time because I don’t like how they fit anymore (like 5 times after I wear them) haha.

  15. Love your tips! I have been struggling with my wardrobe for a while and have been doing all my shopping online only because of all the effort it takes to go in person with my baby. I ended up buying a lot of clothes while I was pregnant thinking I would wear them after pregnancy, but realize how silly that was! Not only has my style changed, but my body and needs have changed too.
    I really like the you say to try on everything with your existing clothes. I make the mistake of not doing this and end up with clothes that just sit in my closet. Great tips! I’m going to make updating my wardrobe a higher priority!

  16. To the first question I have to say that it completely depends on how you define success. If success is defined as a mad dash to the top of the ladder and whoever gets there first is successful then yes having children definitely interferes. But if success is defined as quality of life as in being loved and showing love and having deep, long term relationships that cause you to question the meaning of life and love and art and help you to look at the world through different eyes well then I would say that having children helps you to be successful.

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