Why Is Shopping So Hard?

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Why Is Shopping So Hard?

Shopping is often a pain in the ass – and shopping for clothes can be that much harder.  You head into a store (or look online) knowing what you want, and you either can’t find it, or find it but it’s not in your size or the color you wanted.  Or you wander stores and websites hoping for something to catch your eye, and nothing does.

I work with many clients who hate shopping for clothes, or who have a really hard time and are usually unproductive.  It is different for me – shopping is part of my job, and I need to know where to find what I need for my clients.  And I have a 20+ year background in retail, so I know the ins and outs of how stores work (and how to make them work for you).  But for many people, it’s a challenging chore with minimal reward.

So why is shopping so hard?

Brick and mortar retail is having a very tough time.  Business is scarce, which results in tighter in-store inventories and less help on the sales floor.  Online shopping is the next best option, but you really need to know what you’re looking for or you’ll spend hours perusing websites.  And then there’s the matter of knowing the brands that fit you best and what size you are in which designer.  And then it’s delayed gratification – the anticipation before the arrival, and the hope that it fits/looks good/look the same as it did online.  And one of the hardest things about shopping?  Returns!  There’s a very strong chance that once something is in your house, it will never get sent back.

So why is shopping so hard?  And what can you do to make it better?


Walking into a department store (and even boutiques) can be overwhelming.  There are so many things to look at – the stores purposely create eye-catching displays to draw your attention, so it’s easy to get distracted by the newest colors and prints, even when all you really want is a great pair of black pants (I know this intimately, since I spent years in visual merchandising, where part of my job was to update displays and product placement so that stores looked fresh and new, even when there weren’t any new clothes).

And once you get inside, where do you turn?  Some stores are set up by end use (work, weekend, social), while others are arranged by prices or separated into distinct designer shops.  Once you’re able to find what you’re looking for – can you find your size?  Do they have it in another color?  Are there other similar options you should be considering?


Familiarize yourself with the styles that work for you – take stock of what you already have in your closet, and which styles are your favorites and why.  Is a fit and flare dress the most flattering, or are sheaths best for your figure?  Are skinny jeans your go-to, or do you prefer straight leg or boot cut?  Do you find printed blouses the most versatile, or are solids your wardrobe workhorses?  Once you have a clearer idea as to which fits and styles align with your preferences, body type and lifestyle, you’ll have a better filter and be able to more adeptly hone in on what you need, whether you’re at the mall or cruising the web.

Familiarize yourself with stores/brands that work for you – as time permits, schedule a shopping trip (or do some online research) specifically focused on learning which stores and brands work for you.  Who cuts pants appropriately for your body type?  Where can you find the petite, tall or plus sizes that you need?  Which store carries styles you love at a price you can afford?  After you’ve put in some time and energy, you’ll be able to target specific stores, designers and departments on future shopping trips.

SHOPPING TIP: Bloomingdale’s stores are arranged by designer, but Nordstroms are arranged by price.

Ask for help – yes, there are times that you just want to wander on your own and check out the store.  But there are also times that you have a specific purpose in mind – so just ask.  Even when salespeople are scarce, hunt one down and let them know what you want.  It’s their job to help, so they can, at minimum, find another size or let you know where more options are placed.

SHOPPING TIP: When a store appears essentially devoid of sales help, you’ll almost always find someone at the register or in the fitting rooms.

Why Is Shopping So Hard?


Some salespeople can be super helpful – and some, not so much.  If you’re lucky, you’ll land upon a career salesperson that is familiar with the product, knows which styles flatter different body types, and is aware of what’s in current inventory.  But if you’re not as fortunate, you’ll end up with someone who only works once a week, isn’t aware of the latest floor moves and doesn’t have the knowledge to enhance your shopping experience.  And never forget – a salesperson’s ultimate job is to make you spend money.  In one of my first retail jobs, there was a saying – SWAT, standing for Sell What’s Available Today.  Sales people are judged on various goals – overall sales $, units per transaction, credit card acquisition, etc.  They are rarely judged on the quality of the interaction, or the ability to create and engage loyal customers.


Be clear with what you’re looking for – whether it’s a search for the ever-elusive perfect white blouse, something to wear with a skirt you already own, or the location of markdowns – clearly communicate your needs.  And even feel free to tell them that you’re okay right now, but they can check back with you in ten minutes (because you might not be able to find help when you’re ready for it).

Don’t be shy about your budget – it’s not always easy to find what you want at the price you’re willing to pay, so don’t be shy about communicating your budget.  It will truly help the sales person to know how much you want to spend, or even a range so that they can more accurately guide you to what works.

SHOPPING TIP: Don’t be shy about asking other questions – such as, “when is the next delivery?” or “what days do you do markdowns?” At best, you’ll get the answers you need – and at worst, you’ll find out if the sales person is knowledgeable or not.

Be prepared – if this is a shopping trip with a distinct focus and/or your time is limited, do your homework and arrive prepared with your needs.  That way, if you do find an amazing salesperson, you can ask for what you want at your budgeted price, and they can let you know if they have it.  And if they do, great!  And if not – on to the next store…

SHOPPING TIP: If you frequent a store, find the salespeople that you see all the time.  They’re most likely the ones that work more hours and/or have the most knowledge.


You most often go food shopping with a list, right?  But do you go clothes shopping with a list?  The same way that you’re filling the holes in your pantry at the grocery store, you’re filling the holes in your wardrobe at the mall or online.  So if you’ve ever found yourself buying the same thing over and over, spending more than you should, or tiring out before you hit the goal of the trip, devoting some time to preparing and planning will pay off in droves.


Know what you need – a great way to know what you need is to go through your closet seasonally (or annually), to pinpoint the holes that keep you from creating fabulous outfits that make you feel confident and ready to conquer your day.  But if a closet audit isn’t on your agenda, there are other ways.  Keep a pad on your dresser, and when you’re getting dressed and can’t complete an outfit – write down what’s missing.  And think through what’s coming up over the next several months: vacations, weddings, important meetings, and anything that would require something your wardrobe can’t currently fulfill.

SHOPPING TIP: Do whatever you can to avoid desperation shopping.  The same way that food shopping while you’re hungry leads to less-than-ideal results, clothes shopping the day before an event may lead to buyers’ remorse.

Know your budget – you don’t need to determine an overall dollar amount that you’re willing to devote to your wardrobe for the upcoming season, but you do need to know how much you’re willing to spend for a pair of jeans or an investment blazer.  I call these your ‘item thresholds’.  You may have never thought of it before, but if you take a few minutes, you can easily determine what they are – then write them down and put them in your wallet (or as a note in your phone) to refer to if you’ve ever accidentally spent more than intended.

Plan your shopping trip – shopping can be exhausting, so create a situation where you can be successful (and avoid one where you can’t).  If you’re a morning person, hit the stores on Saturday right when they open, with the goal of being done by lunchtime – as opposed to after a long workday.  If you prefer shopping in the evening, have a light dinner and set aside a few hours with a clear goal.  If you’re online shopping, give yourself a time limit along with your list.  Also – it pays to strategize which stores you’ll visit and what you hope to find in each.  Yes, there’s always the possibility of finding hidden treasure in a new location, but a game plan never hurts.

SHOPPING TIP: If you don’t have time to try clothes on, you don’t have time to shop.  Or else you may find yourself back at the store doing returns, when five minutes in the fitting room could have saved you a trip.


For the same reason that you don’t cut your own hair or do your own plumbing – when it’s not your expertise, you call in an expert.  So if it’s time to review and renew your closet, define and refine your style, or if want the process of building a wardrobe to be more efficient, more productive, and actually enjoyable, just let me know.


2 Responses

  1. Great tips, very helpful!

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