A Friendly Guide to Avoid Awkward Gifts
Shopping for other people's clothes is often a minefield. So often we want to buy something to be thoughtful, but end up causing embarrassment or discomfort for the recipient. Sizes, styles, cuts and personal preferences all have to be considered, and one misstep could turn pleasure into polite horror. However, with some forethought and some useful strategies, you can avoid the pain and have some fun!
1. Guess Their Size Without Any Clues
No two bodies are exactly the same, even if they appear to be at first glance. Trying to determine someone’s size by eye is nearly as easy as threading a needle with your toes. Guessing can lead to an awkward situation instead of a thoughtful one.
2. Ignore Their Personal Style
Purchasing a piece that clashes with how they normally dress conveys a lack of interest or even care in them. A neutral basics-lover will never wear a loud graphic tee, so why buy it for them? A gift should be a reflection of themself, not you.
3. Buy Clothes That Need “Confidence” to Wear
Big statement items and especially anything sheer and body-hugging are difficult to give, unless you know they have an appreciation for such eye-catching attention. Dressing outside of your comfort zone can be intimidating, and clothes that feel that way often end up not getting worn. It’s a waste of money, and it shows you don’t really know the person.
4. Choose the Wrong Occasion for the Item
Sending your partner bulky winter clothing is fun until they live in a hot and humid area. Picking formal pieces over more relaxed clothing also can backfire if they’re not going to a corporate office each day. Occasion matters when you live outside your own closet.
5. Forget to Check the Return Policy
When returning clothing is a challenge, one sizing mistake can make you a household pariah. Always, always make sure there’s an easy way to return the item if need be. It’s easier for everyone.
6. Buy Something That Requires Extra Effort
Dry-clean-only or fabrics that wrinkle easily can add extra work to someone’s routine, rather than being a joyful gift. It’s a personal choice, but not everyone wants that kind of maintenance in their life. Opting for low-effort clothing means more frequent wear.
micheile henderson on Unsplash
7. Assume One Brand Fits Like Another
Sizes can be all over the map even when the label claims it’s the same number as another. They call it fashion for a reason, and that goes double when you’re buying for someone else. Familiarity with a brand makes a major difference.
8. Overlook Fabric Preferences
Not everyone can wear itchy fabrics or stiff clothing, no matter how stylish. Choosing to ignore this can leave you with an unwearable gift. Texture is key when picking out pieces for someone else.
9. Buy Trendy Pieces That Won’t Last
Hyper-trendy styles and clothing will likely feel dated within months, so know the person’s threshold for chasing trends. It’s better to err on the side of timeless gifts than try to keep up. It might be fun for a moment, but after it passes it’s just another piece of cloth.
10. Make It About Your Taste
Easier said than done, but your goal here is to make them feel good about the gift. Picking something you love rather than what they want is a gift gifting fail. When it becomes more about you than them, the gift loses impact.
Knowing what to avoid is half the battle, and once that’s under your belt, it’s much easier to keep your eye on what you should be doing.
1. Check Their Closet for Clues
See what they wear most and what they seem to be missing in their closet. If they gravitate toward certain colors, fits, and fabrics, these are your clues. It’s much more useful than blind guessing.
Priscilla Du Preez 🇨🇦 on Unsplash
2. Stick With Brands They Already Love
Know where they like to shop? You’re already 90% of the way there. Odds are much higher that you’ll pick the right fit and style with a brand they already trust and wear. It’s also a signal you pay attention.
3. Size Up When You’re Unsure
It’s almost always better to size up if you’re not sure. Most people prefer a looser fit, or it’s easier to tailor if necessary. Tight-fitting clothing is almost never worn unless it’s perfect.
4. Choose Versatile Basics
Neutral colors and timeless silhouettes have universal application. Items like these will blend seamlessly into someone’s wardrobe with minimal effort. Versatile pieces take the risk factor out of a gift.
5. Pay Attention to Fabric Quality
Breathable, soft fabrics are likely to be a hit. High-quality fabric tends to feel nicer even before it’s worn. Comfort is a win with everyone.
Daniele Levis Pelusi on Unsplash
6. Keep the Receipt or Gift Option Handy
Adding a gift receipt is a thoughtful addition that demonstrates you weren’t just throwing darts in the dark. It allows them to make the choice with less pressure and no awkward conversation required. A flexible safety net can make it feel less stressful.
7. Think About Their Lifestyle
How does the person spend most of their time? Do they have to look “presentable” for work, or are they at home in pajamas all day? Focusing on how they live their life will make the gift feel more thought-through. Lifestyle-focused gifts will also get worn more often.
8. When in Doubt, Accessories Can Help
Scarves, socks, hats, and outer layers are more forgiving than fitted items. They can still feel personal without relying on size as much. Risking a little can still allow for a thoughtful gift without crossing into stress territory.
9. Ask Subtle Questions Ahead of Time
Casually conversing about shopping trips or favorite stores can be insightful. You don’t have to give any indication that you’re buying a gift, but a little curiosity now can spare you stress later. Putting in just a bit of effort can result in a much more thoughtful gift that actually gets worn.
10. Trust Thoughtfulness Over Perfection
A thoughtful gift is usually worth more than a flawless one. When they can see the care you put into choosing it, they’ll be much more likely to appreciate it. Clothing gifts don’t need to be perfect to be meaningful.


















